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1000 Longboat Club Road Unit 1105, Longboat Key

Seller wants offers! Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the luxurious St. Regis Resort. This island gem has brought many years of joy to the Seller based on its perfect South LBK beachside location and all it's resort style amenities. The sleek European style interior boasts carefree luxury vinyl plank flooring, along with new carpeting in both bedrooms, LED lighting, dazzling designer tile in both bathrooms, and the color scheme throughout mirrors its direct seaside setting. The open-concept kitchen makes entertaining a breeze and offers gorgeous quartz counter tops, custom backsplash, stylish GE appliances, sparkling hardware, and a customized breakfast bar. Both the primary and guest bedroom each lead to a separate balcony where you can soak up the sun while enjoying the peaceful surroundings and endless water and beach views. Residents enjoy the convenience of on-site management, an updated guest suite & additional guest quarters for your overflow visitors, a secure lobby, tennis and pickle ball, heated pool and spa, a great gym, and a refurbished lobby, hallways, social room, community bathrooms, and the landscaping create an even more exceptional experience in this world-class beach location. A membership to Longboat Key Club’s exceptional offerings will provide many hours of outdoor fun and golf & tennis enthusiasts will appreciate the two championship courses & tennis gardens. These facilities, along with professional instruction and well-appointed pro shops, cater to athletes of all levels. Outside the gates, Longboat Key offers fine & casual dining, deep water boating & fishing, 10 miles of sugar sand beaches, and a great variety of local treasures to explore. The Sarasota Opera & Ballet, Van Wezel Performing Arts, and all of Sarasota's cultural offerings including boutique shopping and popular restaurants are just minutes away, creating the perfect balance of relaxation and activity in this sought-after island paradise.

2 Beds ⋅ 2 Baths ⋅ Privateer South SubDv. ⋅ 34228 Zip Code

Seller wants offers! Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the luxurious St. Regis Resort. This island gem has brought many years of joy to the Seller based on its perfect South LBK beachside location and all it's resort style amenities. The sleek European style interior boasts carefree luxury vinyl plank flooring, along with new carpeting in both bedrooms, LED lighting, dazzling designer tile in both bathrooms, and the color scheme throughout mirrors its direct seaside setting. The open-concept kitchen makes entertaining a breeze and offers gorgeous quartz counter tops, custom backsplash, stylish GE appliances, sparkling hardware, and a customized breakfast bar. Both the primary and guest bedroom each lead to a separate balcony where you can soak up the sun while enjoying the peaceful surroundings and endless water and beach views. Residents enjoy the convenience of on-site management, an updated guest suite & additional guest quarters for your overflow visitors, a secure lobby, tennis and pickle ball, heated pool and spa, a great gym, and a refurbished lobby, hallways, social room, community bathrooms, and the landscaping create an even more exceptional experience in this world-class beach location. A membership to Longboat Key Club’s exceptional offerings will provide many hours of outdoor fun and golf & tennis enthusiasts will appreciate the two championship courses & tennis gardens. These facilities, along with professional instruction and well-appointed pro shops, cater to athletes of all levels. Outside the gates, Longboat Key offers fine & casual dining, deep water boating & fishing, 10 miles of sugar sand beaches, and a great variety of local treasures to explore. The Sarasota Opera & Ballet, Van Wezel Performing Arts, and all of Sarasota's cultural offerings including boutique shopping and popular restaurants are just minutes away, creating the perfect balance of relaxation and activity in this sought-after island paradise.

1000 Longboat Club Road Unit 1105, Longboat Key

1241 Gulf Of Mexico Drive Unit 109, Longboat Key

$950,000

Experience refined coastal living at The Water Club on Longboat Key, where lush tropical grounds meet the Gulf’s powdery white-sand beaches and shimmering aquamarine waters. Priced well below market value, this move-in ready, beautifully appointed Thomas Moser turnkey-furnished residence offers 2,000 square feet of thoughtfully designed living space, with two split-plan bedrooms, two full baths, a convenient powder room and a separate full-size laundry room with sink. Each spacious bedroom features a private en-suite bath, while 10-foot ceilings, warm wood flooring, and floor-to-ceiling hurricane-impact windows and sliders create an inviting sense of light and scale. The exceptional primary suite includes a generous walk-in closet and direct access to the private balcony. At the heart of the home, the expertly remodeled kitchen showcases custom cabinetry, a glass-mosaic backsplash, reverse-osmosis faucet, and premium stainless-steel appliances, including a Viking range and Sub-Zero refrigerator. A separate dry bar with Sub-Zero wine and beverage refrigerators adds effortless style for entertaining. The expansive terrace overlooks peaceful tropical foliage, offering a private setting for morning coffee or evening relaxation. Positioned on the plaza level, the residence provides convenient access to The Water Club’s world-class amenities, including 24-hour guard-gated security, concierge services, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and more than 16 acres of pristine beachfront grounds. Just a short drive from St. Armands Circle and downtown Sarasota, this distinguished residence places world-class dining, shopping, arts, and culture nearby. Discover timeless elegance, modern comfort, and an incomparable Gulf Coast lifestyle at The Water Club.

2 Beds ⋅ 3 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code

Experience refined coastal living at The Water Club on Longboat Key, where lush tropical grounds meet the Gulf’s powdery white-sand beaches and shimmering aquamarine waters. Priced well below market value, this move-in ready, beautifully appointed Thomas Moser turnkey-furnished residence offers 2,000 square feet of thoughtfully designed living space, with two split-plan bedrooms, two full baths, a convenient powder room and a separate full-size laundry room with sink. Each spacious bedroom features a private en-suite bath, while 10-foot ceilings, warm wood flooring, and floor-to-ceiling hurricane-impact windows and sliders create an inviting sense of light and scale. The exceptional primary suite includes a generous walk-in closet and direct access to the private balcony. At the heart of the home, the expertly remodeled kitchen showcases custom cabinetry, a glass-mosaic backsplash, reverse-osmosis faucet, and premium stainless-steel appliances, including a Viking range and Sub-Zero refrigerator. A separate dry bar with Sub-Zero wine and beverage refrigerators adds effortless style for entertaining. The expansive terrace overlooks peaceful tropical foliage, offering a private setting for morning coffee or evening relaxation. Positioned on the plaza level, the residence provides convenient access to The Water Club’s world-class amenities, including 24-hour guard-gated security, concierge services, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and more than 16 acres of pristine beachfront grounds. Just a short drive from St. Armands Circle and downtown Sarasota, this distinguished residence places world-class dining, shopping, arts, and culture nearby. Discover timeless elegance, modern comfort, and an incomparable Gulf Coast lifestyle at The Water Club.

1241 Gulf Of Mexico Drive Unit 109, Longboat Key

$950,000

Laid-back Living on Longboat Key -- A Boater's Paradise! Welcome to 744 Jungle Queen Way, a fully renovated, FURNISHED 3-bedroom, 2-bathroom coastal retreat on the stunning Longboat Key! Whether you're a boating enthusiast, a beachcomber, or someone who just loves the island life, this home delivers the ultimate Florida lifestyle. ***Prime Location & Waterfront Living Nestled just seven homes away from Sarasota Bay, this property is a boater's dream with two boat lifts, offering quick access to the Gulf of Mexico's crystal-clear waters. Spend your days fishing, cruising, or island-hopping--all from your backyard! ***Deeded Beach Access - Just 777 Steps to Paradise... take a short stroll across Gulf of Mexico Drive and find yourself on the powdery sands of Longboat Key's legendary beaches. Enjoy sun-soaked days, breathtaking sunsets, and gentle Gulf breezes right outside your door. ***Close to Local Favorites & Hidden Gems. In just a short walk, you'll find island hotspots like the Lo'Key Island Grille, Guppy's Restaurant, and the award-winning Euphemia Haye. A short boat ride, you can enjoy The Shore, Cortez Kitchen, Swordfish Grille, Tide Tables, Anna Maria Oyster Bar, Bridgetenders and Dockside restaurants. ***Modern Updates with Coastal Charm. Step inside to an open-concept layout featuring a spacious, upgraded kitchen with solid wood cabinetry and stone countertops -- perfect for entertaining. The home's split-bedroom design ensures privacy, while the extra-wide lot provides a natural buffer between properties for peace and tranquility. ***Take a short scenic 1-mile stroll from your front door to enjoy the beauty of Florida's coastal landscape at Joan M. Durante Park and the Sarasota Bay overlook dock for a peaceful escape. This 32-acre bay front nature preserve features winding boardwalks, shaded trails, and scenic waterfront views, perfect for birdwatching, peaceful walks, or catching a sunrise over the mangroves. ***Your Slice of Island Paradise Awaits! Whether you're looking for a full-time residence, a vacation getaway, or an investment property, this home captures the essence of laid-back luxury. Don't miss your chance to live the dream on Longboat Key! ***Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Laid-back Living on Longboat Key -- A Boater's Paradise! Welcome to 744 Jungle Queen Way, a fully renovated, FURNISHED 3-bedroom, 2-bathroom coastal retreat on the stunning Longboat Key! Whether you're a boating enthusiast, a beachcomber, or someone who just loves the island life, this home delivers the ultimate Florida lifestyle. ***Prime Location & Waterfront Living Nestled just seven homes away from Sarasota Bay, this property is a boater's dream with two boat lifts, offering quick access to the Gulf of Mexico's crystal-clear waters. Spend your days fishing, cruising, or island-hopping--all from your backyard! ***Deeded Beach Access - Just 777 Steps to Paradise... take a short stroll across Gulf of Mexico Drive and find yourself on the powdery sands of Longboat Key's legendary beaches. Enjoy sun-soaked days, breathtaking sunsets, and gentle Gulf breezes right outside your door. ***Close to Local Favorites & Hidden Gems. In just a short walk, you'll find island hotspots like the Lo'Key Island Grille, Guppy's Restaurant, and the award-winning Euphemia Haye. A short boat ride, you can enjoy The Shore, Cortez Kitchen, Swordfish Grille, Tide Tables, Anna Maria Oyster Bar, Bridgetenders and Dockside restaurants. ***Modern Updates with Coastal Charm. Step inside to an open-concept layout featuring a spacious, upgraded kitchen with solid wood cabinetry and stone countertops -- perfect for entertaining. The home's split-bedroom design ensures privacy, while the extra-wide lot provides a natural buffer between properties for peace and tranquility. ***Take a short scenic 1-mile stroll from your front door to enjoy the beauty of Florida's coastal landscape at Joan M. Durante Park and the Sarasota Bay overlook dock for a peaceful escape. This 32-acre bay front nature preserve features winding boardwalks, shaded trails, and scenic waterfront views, perfect for birdwatching, peaceful walks, or catching a sunrise over the mangroves. ***Your Slice of Island Paradise Awaits! Whether you're looking for a full-time residence, a vacation getaway, or an investment property, this home captures the essence of laid-back luxury. Don't miss your chance to live the dream on Longboat Key! ***Schedule your private showing today!

744 Jungle Queen Way, Longboat Key

1425 Gulf Of Mexico Drive Unit 308, Longboat Key

$950,000

Huge $100,000 price adjustment and it’s comes TURN Key furnished. Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key at Players Club. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a Queen-size bed, wake up to view of the Gulf, access to the terrace/lania, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. Brand new hot water heat 2026, and HVAC unit 2021 and comes with a transferable maintenance contract with Home-Tec. The Players Club elevates coastal living with all the resort-style amenities you will need, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. This community also has rental opportunities of monthly rentals 12 times per year. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.

3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code

Huge $100,000 price adjustment and it’s comes TURN Key furnished. Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key at Players Club. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a Queen-size bed, wake up to view of the Gulf, access to the terrace/lania, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. Brand new hot water heat 2026, and HVAC unit 2021 and comes with a transferable maintenance contract with Home-Tec. The Players Club elevates coastal living with all the resort-style amenities you will need, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. This community also has rental opportunities of monthly rentals 12 times per year. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.

1425 Gulf Of Mexico Drive Unit 308, Longboat Key

1055 Gulf Of Mexico Drive Unit 402, Longboat Key

$950,000

This direct Gulf-front residence at Beachplace presents a rare opportunity to create your dream retreat in one of Longboat Key’s most desirable communities. Positioned to capture unobstructed views of the Gulf of Mexico, this two-bedroom getaway offers the ideal canvas for personal renovation, combining a beachfront lifestyle with outstanding rental potential. Step into a light-filled floorplan where the welcoming foyer flows into a spacious living and dining area, framed by new, impact walls of glass that draw in sweeping coastal vistas. The highlight of the home is the expansive beachfront terrace—perfect for savoring evening sunsets and refreshing Gulf breezes.The smartly designed split-bedroom layout provides ideal separation for hosting guests, with the primary suite offering direct access to the terrace, a spacious closet, and an en-suite bath. Whether reimagining this residence for personal use or income generation, the fundamental elements are already in place: a premier beachfront location, brand-new windows and doors, plus a generous square footage, with a layout that maximizes privacy and views. Additional conveniences include a rare combination of one coveted covered parking space and an additional outdoor spot, offering ease for seasonal residents or visitors. Beachplace is a sought-after Gulf-front community known for its pristine beachfront access and resort-style amenities. Residents enjoy a 24-hour staffed guard gate, on-site management, a newly refreshed clubhouse, tennis courts, a well-equipped fitness center, heated swimming pool, and spa—everything needed for the quintessential Florida lifestyle. Perfectly located on the southern end of Longboat Key, this residence is just moments from the Longboat Key Club’s golf and tennis facilities. Enjoy a quick drive to the convenience of Avenue of the Flowers shopping plaza or indulge in the world-class dining and boutique shopping of St. Armands Circle. For cultural outings, downtown Sarasota offers renowned theaters, galleries, and waterfront parks just minutes away.

2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code

This direct Gulf-front residence at Beachplace presents a rare opportunity to create your dream retreat in one of Longboat Key’s most desirable communities. Positioned to capture unobstructed views of the Gulf of Mexico, this two-bedroom getaway offers the ideal canvas for personal renovation, combining a beachfront lifestyle with outstanding rental potential. Step into a light-filled floorplan where the welcoming foyer flows into a spacious living and dining area, framed by new, impact walls of glass that draw in sweeping coastal vistas. The highlight of the home is the expansive beachfront terrace—perfect for savoring evening sunsets and refreshing Gulf breezes.The smartly designed split-bedroom layout provides ideal separation for hosting guests, with the primary suite offering direct access to the terrace, a spacious closet, and an en-suite bath. Whether reimagining this residence for personal use or income generation, the fundamental elements are already in place: a premier beachfront location, brand-new windows and doors, plus a generous square footage, with a layout that maximizes privacy and views. Additional conveniences include a rare combination of one coveted covered parking space and an additional outdoor spot, offering ease for seasonal residents or visitors. Beachplace is a sought-after Gulf-front community known for its pristine beachfront access and resort-style amenities. Residents enjoy a 24-hour staffed guard gate, on-site management, a newly refreshed clubhouse, tennis courts, a well-equipped fitness center, heated swimming pool, and spa—everything needed for the quintessential Florida lifestyle. Perfectly located on the southern end of Longboat Key, this residence is just moments from the Longboat Key Club’s golf and tennis facilities. Enjoy a quick drive to the convenience of Avenue of the Flowers shopping plaza or indulge in the world-class dining and boutique shopping of St. Armands Circle. For cultural outings, downtown Sarasota offers renowned theaters, galleries, and waterfront parks just minutes away.

1055 Gulf Of Mexico Drive Unit 402, Longboat Key

5311 Gulf Of Mexico Drive Unit 3, Longboat Key

$950,000

Turnkey furnished and positioned directly on the sandy shores of the Gulf of Mexico, this first-floor, direct Gulf-front residence at Beach Castle Resort offers an exceptional blend of beachfront living and proven rental performance. Averaging six figures in annual gross income, this two-bedroom retreat is ideal for personal enjoyment, weekly rentals, or a combination of both—making it one of Longboat Key’s strongest investment opportunities. The light-filled interior features oversized tile flooring, updated windows and sliders (2009), and a well-appointed kitchen with granite countertops, contemporary cabinetry, modern appliances, and plumbing and electrical upgrades completed in 2006. Designed for effortless coastal living, the open layout seamlessly connects the kitchen, dining, and living areas. Floor-to-ceiling sliders lead to a private patio and screened-in lanai, both just steps from the beach, allowing indoor and outdoor spaces to flow together naturally. The split-bedroom plan enhances privacy for owners and guests. The primary suite enjoys beautiful Gulf views, private patio access, and a peaceful setting perfect for morning coffee or sunset unwinding. A comfortable second bedroom and full bath complete the guest wing. Beach Castle Resort is one of the few communities on Longboat Key offering daily, weekly, or monthly rental flexibility, giving owners the freedom to maximize both personal use and rental income. The community’s beach-to-bay amenities include deeded beach access, a sundeck with heated swimming pool and spa, barbecue grilling areas, a fishing pier, and a day dock for boating enthusiasts (first-come basis, no overnight docking). Lush tropical landscaping and well-maintained grounds create a relaxing boutique-resort environment. Perfectly located on the north end of Longboat Key, the property is minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic walking and biking routes. A short drive south leads to the Longboat Key Club, upscale dining, and the attractions of St. Armands Circle. Downtown Sarasota—home to world-class theater, museums, botanical gardens, professional events, and waterfront parks—is just across the bridge. With direct Gulf-front views, strong rental history, and an unbeatable location, this Beach Castle residence offers the best of Longboat Key’s coastal lifestyle—whether you’re seeking an investment, a getaway, or both.

2 Beds ⋅ 2 Baths ⋅ Mccalls Beach Castle SubDv. ⋅ 34228 Zip Code

Turnkey furnished and positioned directly on the sandy shores of the Gulf of Mexico, this first-floor, direct Gulf-front residence at Beach Castle Resort offers an exceptional blend of beachfront living and proven rental performance. Averaging six figures in annual gross income, this two-bedroom retreat is ideal for personal enjoyment, weekly rentals, or a combination of both—making it one of Longboat Key’s strongest investment opportunities. The light-filled interior features oversized tile flooring, updated windows and sliders (2009), and a well-appointed kitchen with granite countertops, contemporary cabinetry, modern appliances, and plumbing and electrical upgrades completed in 2006. Designed for effortless coastal living, the open layout seamlessly connects the kitchen, dining, and living areas. Floor-to-ceiling sliders lead to a private patio and screened-in lanai, both just steps from the beach, allowing indoor and outdoor spaces to flow together naturally. The split-bedroom plan enhances privacy for owners and guests. The primary suite enjoys beautiful Gulf views, private patio access, and a peaceful setting perfect for morning coffee or sunset unwinding. A comfortable second bedroom and full bath complete the guest wing. Beach Castle Resort is one of the few communities on Longboat Key offering daily, weekly, or monthly rental flexibility, giving owners the freedom to maximize both personal use and rental income. The community’s beach-to-bay amenities include deeded beach access, a sundeck with heated swimming pool and spa, barbecue grilling areas, a fishing pier, and a day dock for boating enthusiasts (first-come basis, no overnight docking). Lush tropical landscaping and well-maintained grounds create a relaxing boutique-resort environment. Perfectly located on the north end of Longboat Key, the property is minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic walking and biking routes. A short drive south leads to the Longboat Key Club, upscale dining, and the attractions of St. Armands Circle. Downtown Sarasota—home to world-class theater, museums, botanical gardens, professional events, and waterfront parks—is just across the bridge. With direct Gulf-front views, strong rental history, and an unbeatable location, this Beach Castle residence offers the best of Longboat Key’s coastal lifestyle—whether you’re seeking an investment, a getaway, or both.

5311 Gulf Of Mexico Drive Unit 3, Longboat Key

$950,000

Welcome to 2323 Harbour Oaks Drive, a light-filled villa with a wide-open layout and peaceful vistas overlooking the Longboat Key Club golf course and a serene pond. Positioned to capture gorgeous natural light throughout the day, this residence lives effortlessly with soaring ceilings, generous room sizes, and seamless indoor–outdoor connection. An inviting great room and dining area open to the screened brand-new pool deck through expansive sliding glass doors, creating the perfect setting for relaxing or entertaining while enjoying views of the fairway and water. The kitchen flows directly into the main living spaces, making daily living simple and intuitive. The spacious primary suite offers privacy, while two additional bedrooms provide flexibility for guests or a home office. Located in Harbour Circle, one of Bay Isles’ most established and well-maintained communities, residents enjoy lush landscaping, a community pool and spa, and exclusive membership to the Bay Isles Beach Club — complete with private parking, pavilion, beach chairs, and direct beach access. Just moments from the Longboat Key Club, with optional membership for golf, tennis, pickleball, fitness, and private dining, the deep-water LBK Moorings Marina, and all the conveniences of Publix, CVS, banks, and boutiques. This location also offers easy access to St. Armands Circle and the cultural amenities of downtown Sarasota.

3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code

Welcome to 2323 Harbour Oaks Drive, a light-filled villa with a wide-open layout and peaceful vistas overlooking the Longboat Key Club golf course and a serene pond. Positioned to capture gorgeous natural light throughout the day, this residence lives effortlessly with soaring ceilings, generous room sizes, and seamless indoor–outdoor connection. An inviting great room and dining area open to the screened brand-new pool deck through expansive sliding glass doors, creating the perfect setting for relaxing or entertaining while enjoying views of the fairway and water. The kitchen flows directly into the main living spaces, making daily living simple and intuitive. The spacious primary suite offers privacy, while two additional bedrooms provide flexibility for guests or a home office. Located in Harbour Circle, one of Bay Isles’ most established and well-maintained communities, residents enjoy lush landscaping, a community pool and spa, and exclusive membership to the Bay Isles Beach Club — complete with private parking, pavilion, beach chairs, and direct beach access. Just moments from the Longboat Key Club, with optional membership for golf, tennis, pickleball, fitness, and private dining, the deep-water LBK Moorings Marina, and all the conveniences of Publix, CVS, banks, and boutiques. This location also offers easy access to St. Armands Circle and the cultural amenities of downtown Sarasota.

2323 Harbour Oaks Drive, Longboat Key

4325 Gulf Of Mexico Drive Unit 102, Longboat Key

$950,000

Experience the relaxed Gulf Coast lifestyle at Tiffany Plaza - direct Gulf-front, accessible community on Longboat Key where every day feels like a beach vacation. Go from your patio onto the sand and enjoy spectacular sunsets. This inviting two-bedroom, two-bath residence offers a spacious open living and dining area ideal for hosting 8-12 guests. Updated with stone countertops, fresh paint, new air conditioner, new hot water heater and hurricane-grade windows. Both elevator and landscape assessments are paid, and there was no storm flooding or damage in 2024, according to the owner. Community amenities include a newly updated pool, barbecue grills, beachside tiki hut, and remodeled clubhouse. Tiffany Plaza is self-managed, well-maintained and beautifully landscaped. HOA fees include cable TV, water, sewer, trash, pool and grounds maintenance, manager and more. Convenient mid-island location near Bayfront Park, dog park, Publix, CVS, shops, dining and fitness centers.

2 Beds ⋅ 2 Baths ⋅ Tiffany Plaza SubDv. ⋅ 34228 Zip Code

Experience the relaxed Gulf Coast lifestyle at Tiffany Plaza - direct Gulf-front, accessible community on Longboat Key where every day feels like a beach vacation. Go from your patio onto the sand and enjoy spectacular sunsets. This inviting two-bedroom, two-bath residence offers a spacious open living and dining area ideal for hosting 8-12 guests. Updated with stone countertops, fresh paint, new air conditioner, new hot water heater and hurricane-grade windows. Both elevator and landscape assessments are paid, and there was no storm flooding or damage in 2024, according to the owner. Community amenities include a newly updated pool, barbecue grills, beachside tiki hut, and remodeled clubhouse. Tiffany Plaza is self-managed, well-maintained and beautifully landscaped. HOA fees include cable TV, water, sewer, trash, pool and grounds maintenance, manager and more. Convenient mid-island location near Bayfront Park, dog park, Publix, CVS, shops, dining and fitness centers.

4325 Gulf Of Mexico Drive Unit 102, Longboat Key

210 Sands Point Road Unit 2405, Longboat Key

$948,000

Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suite at Inn on the Beach offers a unique opportunity to own within the prestigious Longboat Key Club Resort. Spanning 650 sq. ft., this residence provides both convenience and privacy, with an expansive covered terrace offering peaceful Gulf views while keeping you close to every amenity. Completely renovated and meticulously styled, the interior pairs warm wood accents with neutral tones, complemented by faux wood tile floors flowing throughout. Dual sliders frame shimmering Gulf waters and invite natural light into the living space. The kitchen is a standout, with stone countertops, harmonizing cabinetry with glass panel accents and a colorful tile backsplash that adds just the right touch of vibrancy. Off the bedroom space, a beautifully updated bath features all-white cabinetry, a separate water closet and a glass walk-in shower with striking tilework. For added ease, in-unit laundry utilities are included. This unit participates in the Resort Rental Program and has a healthy rental history, with nightly rentals allowed, making it both an enjoyable retreat and a strong investment. As an owner, you’ll have access to the exclusive amenities of the 410-acre Longboat Key Club, including 45 holes of championship golf, 20 Har-Tru tennis courts at the award-winning Tennis Gardens, a full-service marina, private Gulf-front beach with umbrellas and attendant service, a world-class fitness and wellness center, spa and five private dining options. Recently renovated guest services, dining areas, and resort amenities have elevated the experience even further, earning accolades such as the AAA Four-Diamond Award and recognition from Condé Nast Traveler as a Top Florida Resort.

1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code

Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suite at Inn on the Beach offers a unique opportunity to own within the prestigious Longboat Key Club Resort. Spanning 650 sq. ft., this residence provides both convenience and privacy, with an expansive covered terrace offering peaceful Gulf views while keeping you close to every amenity. Completely renovated and meticulously styled, the interior pairs warm wood accents with neutral tones, complemented by faux wood tile floors flowing throughout. Dual sliders frame shimmering Gulf waters and invite natural light into the living space. The kitchen is a standout, with stone countertops, harmonizing cabinetry with glass panel accents and a colorful tile backsplash that adds just the right touch of vibrancy. Off the bedroom space, a beautifully updated bath features all-white cabinetry, a separate water closet and a glass walk-in shower with striking tilework. For added ease, in-unit laundry utilities are included. This unit participates in the Resort Rental Program and has a healthy rental history, with nightly rentals allowed, making it both an enjoyable retreat and a strong investment. As an owner, you’ll have access to the exclusive amenities of the 410-acre Longboat Key Club, including 45 holes of championship golf, 20 Har-Tru tennis courts at the award-winning Tennis Gardens, a full-service marina, private Gulf-front beach with umbrellas and attendant service, a world-class fitness and wellness center, spa and five private dining options. Recently renovated guest services, dining areas, and resort amenities have elevated the experience even further, earning accolades such as the AAA Four-Diamond Award and recognition from Condé Nast Traveler as a Top Florida Resort.

210 Sands Point Road Unit 2405, Longboat Key

210 Sands Point Road Unit 2402, Longboat Key

$935,000

The Resort at Longboat Key Club – Gulf Front Condo-Hotel Investment Opportunity Best Priced Beachview Condo. Rxperience the best of coastal luxury and income-producing ownership at The Resort at Longboat Key Club. This beautifully renovated, turnkey one-bedroom Club Suite offers breathtaking direct views of the Gulf of Mexico, overlooking both the pristine beach and resort-style pool. Designed for effortless ownership, this exceptional residence is currently enrolled in the resort's rental program and professionally managed in partnership with Opal Hospitality, allowing owners to enjoy personal use while generating rental income.Whether you're seeking a vacation retreat, an investment property, or both, this Gulf-front suite delivers an unparalleled resort lifestyle. Ideally located just minutes from St. Armands Circle, you'll enjoy easy access to boutique shopping, exceptional restaurants, arts, culture, and all that Sarasota's Gulf Coast has. Recent renovations provide a fresh, modern coastal aesthetic, making this residence truly move-in ready. Don't miss this rare opportunity to own a piece of paradise in one of Florida's most sought-after luxury resort destinations. Enjoy the benefits of resort ownership, professional management, and spectacular Gulf views—all in one extraordinary property. Guests and owners alike enjoy world-class amenities, including: 45 holes of championship golf Award-winning tennis facilities Full-service marina Luxury spa and wellness services Fine dining and resort lounges Beachfront pool and private beach access Concierge and maid service

1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code

The Resort at Longboat Key Club – Gulf Front Condo-Hotel Investment Opportunity Best Priced Beachview Condo. Rxperience the best of coastal luxury and income-producing ownership at The Resort at Longboat Key Club. This beautifully renovated, turnkey one-bedroom Club Suite offers breathtaking direct views of the Gulf of Mexico, overlooking both the pristine beach and resort-style pool. Designed for effortless ownership, this exceptional residence is currently enrolled in the resort's rental program and professionally managed in partnership with Opal Hospitality, allowing owners to enjoy personal use while generating rental income.Whether you're seeking a vacation retreat, an investment property, or both, this Gulf-front suite delivers an unparalleled resort lifestyle. Ideally located just minutes from St. Armands Circle, you'll enjoy easy access to boutique shopping, exceptional restaurants, arts, culture, and all that Sarasota's Gulf Coast has. Recent renovations provide a fresh, modern coastal aesthetic, making this residence truly move-in ready. Don't miss this rare opportunity to own a piece of paradise in one of Florida's most sought-after luxury resort destinations. Enjoy the benefits of resort ownership, professional management, and spectacular Gulf views—all in one extraordinary property. Guests and owners alike enjoy world-class amenities, including: 45 holes of championship golf Award-winning tennis facilities Full-service marina Luxury spa and wellness services Fine dining and resort lounges Beachfront pool and private beach access Concierge and maid service

210 Sands Point Road Unit 2402, Longboat Key

$935,000

It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot features a healthy and substantial seawall on a private and quiet street, offering a golden opportunity for a luxury new build. Seller will offer house plans from a reputable LBK coastal builder, Brista Homes (plan buyer expense). The Buttonwood Community has been touted by the Longboat Observer as the neighborliest neighborhood on Longboat Key and is unique for having its safe harbor, boat ramp and boat slips up to 28 feet for its residents. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. It's all about connectivity. Sarasota SRQ Airport’s soaring success added 20 flights, 20% passenger growth, a new runway and terminal in 2024, ranks No. 1 for the fastest-growing airport in the U.S., and ranks No. 1 best resort airport in the entire country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. Beyond the numbers is the intangible and powerful increase in consumer confidence, which has always proven to enormously influence the housing market, especially luxury and second-home purchases. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025. Gov. Ron Desantis announced February 20, 2026, another record-breaking year for tourism in Florida welcomed 143.3 million visitors throughout 2025. An estimated 33.5 million visitors as the highest fourth quarter for visitation on record. According to the release, Florida is the #1 domestic travel destination in the U.S. and a standout choice for international visitors.

3 Beds ⋅ 2 Baths ⋅ Buttonwood Harbor SubDv. ⋅ 34228 Zip Code

It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot features a healthy and substantial seawall on a private and quiet street, offering a golden opportunity for a luxury new build. Seller will offer house plans from a reputable LBK coastal builder, Brista Homes (plan buyer expense). The Buttonwood Community has been touted by the Longboat Observer as the neighborliest neighborhood on Longboat Key and is unique for having its safe harbor, boat ramp and boat slips up to 28 feet for its residents. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. It's all about connectivity. Sarasota SRQ Airport’s soaring success added 20 flights, 20% passenger growth, a new runway and terminal in 2024, ranks No. 1 for the fastest-growing airport in the U.S., and ranks No. 1 best resort airport in the entire country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. Beyond the numbers is the intangible and powerful increase in consumer confidence, which has always proven to enormously influence the housing market, especially luxury and second-home purchases. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025. Gov. Ron Desantis announced February 20, 2026, another record-breaking year for tourism in Florida welcomed 143.3 million visitors throughout 2025. An estimated 33.5 million visitors as the highest fourth quarter for visitation on record. According to the release, Florida is the #1 domestic travel destination in the U.S. and a standout choice for international visitors.

615 Buttonwood Drive, Longboat Key

1425 Gulf Of Mexico Drive Unit 408, Longboat Key

$925,000

Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.

3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code

Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.

1425 Gulf Of Mexico Drive Unit 408, Longboat Key

1000 Longboat Club Road Unit 1103, Longboat Key

$925,000

Perched atop the 11th floor, this penthouse residence at Privateer South captures an extraordinary sweep of views spanning Longboat Key Club’s lush golf course, the expanse of Sarasota Bay, the downtown skyline, and the Gulf of Mexico’s turquoise waves. Offering more than 1,400 square feet, the light-filled interiors flow effortlessly between living, dining, and kitchen spaces, framed by impact windows and glass sliders that open to two private terraces—one Gulf-facing and one Bay-facing—inviting you to enjoy sunrises and sunsets alike. The modernized kitchen balances style and function with quartz countertops, a sleek tile backsplash, shaker cabinetry, and stainless-steel appliances. Porcelain tile flooring adds a timeless touch, enhancing the airy ambiance throughout. The split-bedroom plan ensures privacy when guests visit, with the primary suite offering direct access to the larger terrace, a spacious walk-in closet, and a private en-suite bath, while the guest suite is positioned on the opposite wing with its own serene views. Additional comforts include newer impact-rated windows and sliders, covered parking, and an owner’s storage unit located on the same floor. Privateer South, set directly on the Gulf of Mexico, has recently been enhanced with upgrades that further elevate its appeal, including a newer roof, refreshed lobby, and updated common areas. Residents enjoy a lifestyle that blends leisure and convenience, with a beachside heated pool and spa on an expansive deck, tennis, pickleball, and shuffleboard courts, fitness center, fire pit lounge, barbecue area with outdoor seating, social room with catering kitchen, and guest suites for visitors. On-site management and security provide peace of mind in this sought-after community. Beyond the gates, Longboat Key delivers a lifestyle defined by natural beauty and cultural access. Championship golf and fine dining await for members at the Longboat Key Club, while the boutiques and restaurants of St. Armands Circle are minutes away. Downtown Sarasota, with its world-class theaters, museums, galleries, and vibrant waterfront, is an easy drive south. Award-winning beaches, including those of neighboring Lido and Siesta Key, complete the picture, offering endless opportunities to explore, relax, and savor life on the Gulf Coast. This penthouse is more than a residence—it’s a front-row seat to the very best of Sarasota living.

2 Beds ⋅ 2 Baths ⋅ Privateer South SubDv. ⋅ 34228 Zip Code

Perched atop the 11th floor, this penthouse residence at Privateer South captures an extraordinary sweep of views spanning Longboat Key Club’s lush golf course, the expanse of Sarasota Bay, the downtown skyline, and the Gulf of Mexico’s turquoise waves. Offering more than 1,400 square feet, the light-filled interiors flow effortlessly between living, dining, and kitchen spaces, framed by impact windows and glass sliders that open to two private terraces—one Gulf-facing and one Bay-facing—inviting you to enjoy sunrises and sunsets alike. The modernized kitchen balances style and function with quartz countertops, a sleek tile backsplash, shaker cabinetry, and stainless-steel appliances. Porcelain tile flooring adds a timeless touch, enhancing the airy ambiance throughout. The split-bedroom plan ensures privacy when guests visit, with the primary suite offering direct access to the larger terrace, a spacious walk-in closet, and a private en-suite bath, while the guest suite is positioned on the opposite wing with its own serene views. Additional comforts include newer impact-rated windows and sliders, covered parking, and an owner’s storage unit located on the same floor. Privateer South, set directly on the Gulf of Mexico, has recently been enhanced with upgrades that further elevate its appeal, including a newer roof, refreshed lobby, and updated common areas. Residents enjoy a lifestyle that blends leisure and convenience, with a beachside heated pool and spa on an expansive deck, tennis, pickleball, and shuffleboard courts, fitness center, fire pit lounge, barbecue area with outdoor seating, social room with catering kitchen, and guest suites for visitors. On-site management and security provide peace of mind in this sought-after community. Beyond the gates, Longboat Key delivers a lifestyle defined by natural beauty and cultural access. Championship golf and fine dining await for members at the Longboat Key Club, while the boutiques and restaurants of St. Armands Circle are minutes away. Downtown Sarasota, with its world-class theaters, museums, galleries, and vibrant waterfront, is an easy drive south. Award-winning beaches, including those of neighboring Lido and Siesta Key, complete the picture, offering endless opportunities to explore, relax, and savor life on the Gulf Coast. This penthouse is more than a residence—it’s a front-row seat to the very best of Sarasota living.

1000 Longboat Club Road Unit 1103, Longboat Key

5125 Gulf Of Mexico Drive Unit 7, Longboat Key

$917,000

Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush landscaping and upscale tropical ambiance create an idyllic setting along the stunning Gulf of Mexico, perfect for both personal enjoyment and income generation. Amenities at Seagrape Inn include a private entrance to each condo, a private heated pool, a private beach area with lounge chairs and umbrellas, on-site laundry and ice machine, upgraded Wi-Fi throughout the resort, cable TV, a gazebo with a gas BBQ grill, and beach towels and linens. Unit 7, perched on the second floor, provides breathtaking views of the ocean and the inviting pool below. Upon entry, the condo exudes sophistication, with a thoughtfully designed living space that seamlessly connects the living room, dining area, and upgraded kitchen. The kitchen, recently renovated to perfection, features new cabinets, countertops, recessed lighting, plumbing fixtures, and state-of-the-art appliances. The entire unit has been enhanced with new waterproof LVP flooring, fresh interior paint, and modern light fixtures, ensuring a contemporary and elegant aesthetic throughout. Both bedrooms are tastefully furnished, offering serene retreats after a day at the beach. The bathrooms have been completely remodeled, showcasing new vanities, tile work, shower doors, and plumbing fixtures. Step onto the screened balcony to savor unparalleled views of the ocean, pool, and lush greenery a perfect spot to relax and soak in the tranquil surroundings. Beyond the condo's exquisite interior, significant exterior improvements have been made, including the installation of hurricane windows and doors, new deck waterproofing, and exterior painting. The convenience of a designated parking spot adds to the property’s appeal. Located in a prime area of Longboat Key, this condo provides easy access to the beach, Gulf, and nearby restaurants and shops. Whether you're seeking a lucrative investment or a luxurious personal retreat, this beachfront condo offers an extraordinary opportunity to experience the best of coastal living in an unparalleled location.

2 Beds ⋅ 2 Baths ⋅ Seagrape Inn Condo SubDv. ⋅ 34228 Zip Code

Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush landscaping and upscale tropical ambiance create an idyllic setting along the stunning Gulf of Mexico, perfect for both personal enjoyment and income generation. Amenities at Seagrape Inn include a private entrance to each condo, a private heated pool, a private beach area with lounge chairs and umbrellas, on-site laundry and ice machine, upgraded Wi-Fi throughout the resort, cable TV, a gazebo with a gas BBQ grill, and beach towels and linens. Unit 7, perched on the second floor, provides breathtaking views of the ocean and the inviting pool below. Upon entry, the condo exudes sophistication, with a thoughtfully designed living space that seamlessly connects the living room, dining area, and upgraded kitchen. The kitchen, recently renovated to perfection, features new cabinets, countertops, recessed lighting, plumbing fixtures, and state-of-the-art appliances. The entire unit has been enhanced with new waterproof LVP flooring, fresh interior paint, and modern light fixtures, ensuring a contemporary and elegant aesthetic throughout. Both bedrooms are tastefully furnished, offering serene retreats after a day at the beach. The bathrooms have been completely remodeled, showcasing new vanities, tile work, shower doors, and plumbing fixtures. Step onto the screened balcony to savor unparalleled views of the ocean, pool, and lush greenery a perfect spot to relax and soak in the tranquil surroundings. Beyond the condo's exquisite interior, significant exterior improvements have been made, including the installation of hurricane windows and doors, new deck waterproofing, and exterior painting. The convenience of a designated parking spot adds to the property’s appeal. Located in a prime area of Longboat Key, this condo provides easy access to the beach, Gulf, and nearby restaurants and shops. Whether you're seeking a lucrative investment or a luxurious personal retreat, this beachfront condo offers an extraordinary opportunity to experience the best of coastal living in an unparalleled location.

5125 Gulf Of Mexico Drive Unit 7, Longboat Key

$915,000

NEW PRICE: Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42 villas in Harbour Circle with a community pool and spa and membership access to the deeded private beach club. This home boasts vaulted ceilings, multiple hurricane skylights, hurricane windows, sliders and front door, private atrium and new roof with trusses in 2025, coming completely furnished. Enjoy your morning coffee and dozens of magnificent sunsets on your large two level lanai. Enjoy a walk to Publix, CVS and several Banks close to your community. Only a short drive to Saint Armand's Circle and downtown Sarasota where you will find numerous options for shopping, dinning, theatres, ballet, opera and galleries.

3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code

NEW PRICE: Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42 villas in Harbour Circle with a community pool and spa and membership access to the deeded private beach club. This home boasts vaulted ceilings, multiple hurricane skylights, hurricane windows, sliders and front door, private atrium and new roof with trusses in 2025, coming completely furnished. Enjoy your morning coffee and dozens of magnificent sunsets on your large two level lanai. Enjoy a walk to Publix, CVS and several Banks close to your community. Only a short drive to Saint Armand's Circle and downtown Sarasota where you will find numerous options for shopping, dinning, theatres, ballet, opera and galleries.

2367 Harbour Oaks Drive, Longboat Key

$915,000

HUGH PRICE REDUCTION!!!Welcome to historic Longbeach Village, the first neighborhood, established on Longboat Key in 1885. As you enter The Village you will notice a variety of architectural home styles from the 1930s to the present day reflecting the diversity of the folks who live here. This wonderful home has stunning water views of Sarasota Bay, The Village harbor with its small public beach, the town dock, and the boat ramp all of which serve as community gathering spots to launch your boat, kayaks, canoes, and view sunrises, sunsets, dolphins, manatees, and aquatic birds. Pelicans love this placid harbor. Capture and immerse yourself in these magical surroundings from the spacious elevated second level front deck. The open concept great room with the three sets of French doors and seven windows is flooded with natural light. The kitchen offers bay views and will be the envy of amateur as well as gourmet cooks. Here you will enjoy a Sub-Zero refrigerator, two drawer Sub Zero freezer, Wolf 5 burner range, large Wolf oven, Miele steam oven, Tanzanian granite counter tops, custom German cabinets, large and deep storage drawers, workstation, and travertine floors. The great room includes an abundance of recessed lighting and a free-standing wood burning fireplace on a raised hearth as well as a dining area with a distinctive wood table, benches, and chairs. The primary bedroom has water views, access to the wrap around deck through sliding glass doors, and a large walk-in closet, en-suite bathroom with striking wood vanity and marble-like glass sink and dual rainfall shower heads. The powder room off the great room has high end fixtures. The guest bedroom has twin beds, a ceiling fan and rolling shades to keep the light out. The adjoining room could function as an office, art studio, or an extra bedroom. The bathroom has a shower stall and a walk-in closet. The oversized two car garage has hurricane reinforced doors, windows, a work bench, ample shelving throughout and peg boards for tools. A composite “wood” deck that is impervious to rot and insects, surrounds the entire house creating massive outdoor living space. The back deck, overlooking a beautifully landscaped yard, has a heated hot tub, a dining area which has a new awning, and a staircase leading to the backyard, guest house/studio, and new two-person barrel sauna in 2023. The guest house/studio was totally renovated by current owners in 2015 with new Hardi Board siding and insulation. It could also serve as a recreation room with pool table etc. All windows throughout the structures are hurricane compliant. Meticulous and impeccable pride in ownership can be found in every detail throughout! From this lovely home you can walk to the beach, five restaurants, and Whitney Beach shopping center. The Centre Shops with dining, boutiques, hair salon, UPS store are about three miles south. Bradenton Beach, with its multiple attractions, is less than 1 mile north. Famous St. Armands Circle is eleven miles south. The Villagers meet once a month from October to April for socializing and gathering updates on LBK activities. Offered furnished, completely outfitted, and move in ready excluding original artwork and some personal items.

2 Beds ⋅ 3 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code

HUGH PRICE REDUCTION!!!Welcome to historic Longbeach Village, the first neighborhood, established on Longboat Key in 1885. As you enter The Village you will notice a variety of architectural home styles from the 1930s to the present day reflecting the diversity of the folks who live here. This wonderful home has stunning water views of Sarasota Bay, The Village harbor with its small public beach, the town dock, and the boat ramp all of which serve as community gathering spots to launch your boat, kayaks, canoes, and view sunrises, sunsets, dolphins, manatees, and aquatic birds. Pelicans love this placid harbor. Capture and immerse yourself in these magical surroundings from the spacious elevated second level front deck. The open concept great room with the three sets of French doors and seven windows is flooded with natural light. The kitchen offers bay views and will be the envy of amateur as well as gourmet cooks. Here you will enjoy a Sub-Zero refrigerator, two drawer Sub Zero freezer, Wolf 5 burner range, large Wolf oven, Miele steam oven, Tanzanian granite counter tops, custom German cabinets, large and deep storage drawers, workstation, and travertine floors. The great room includes an abundance of recessed lighting and a free-standing wood burning fireplace on a raised hearth as well as a dining area with a distinctive wood table, benches, and chairs. The primary bedroom has water views, access to the wrap around deck through sliding glass doors, and a large walk-in closet, en-suite bathroom with striking wood vanity and marble-like glass sink and dual rainfall shower heads. The powder room off the great room has high end fixtures. The guest bedroom has twin beds, a ceiling fan and rolling shades to keep the light out. The adjoining room could function as an office, art studio, or an extra bedroom. The bathroom has a shower stall and a walk-in closet. The oversized two car garage has hurricane reinforced doors, windows, a work bench, ample shelving throughout and peg boards for tools. A composite “wood” deck that is impervious to rot and insects, surrounds the entire house creating massive outdoor living space. The back deck, overlooking a beautifully landscaped yard, has a heated hot tub, a dining area which has a new awning, and a staircase leading to the backyard, guest house/studio, and new two-person barrel sauna in 2023. The guest house/studio was totally renovated by current owners in 2015 with new Hardi Board siding and insulation. It could also serve as a recreation room with pool table etc. All windows throughout the structures are hurricane compliant. Meticulous and impeccable pride in ownership can be found in every detail throughout! From this lovely home you can walk to the beach, five restaurants, and Whitney Beach shopping center. The Centre Shops with dining, boutiques, hair salon, UPS store are about three miles south. Bradenton Beach, with its multiple attractions, is less than 1 mile north. Famous St. Armands Circle is eleven miles south. The Villagers meet once a month from October to April for socializing and gathering updates on LBK activities. Offered furnished, completely outfitted, and move in ready excluding original artwork and some personal items.

691 Linley Street, Longboat Key

$914,750

Discover coastal tranquility and timeless island charm in this beautifully renovated five- bedroom, three and 1/2 bath residence nestled in the highly sought-after Longbeach Village community at the north end of Longboat Key. Offering over 2,700 square feet of thoughtfully redesigned living space, this impressive two-story home seamlessly blends classic character with modern luxury. The designer kitchen is a chef's dream and showcases quartz countertops, custom cabinetry, newer appliances, and updated flooring. The entire first floor has been fully updated, featuring new electrical, drywall, stylish interior doors, and reimagined spa-like bathrooms. Additional upgrades include impact-rated French entry doors, a new impact-rated foyer door, two new HVAC systems, a tankless water heater, and a new pool pump. Upstairs, soaring ceilings and abundant natural light create an airy, welcoming ambiance. Step outside to your private tropical oasis, where a resort-style pool and spa invite you to swim, relax, or entertain in style. Lush landscaping, a fully fenced yard, an upper balcony with serene views, and a generous covered poolside deck provide multiple spaces to unwind and enjoy the Florida lifestyle. Longbeach Village is a historic and vibrant bayfront community celebrated for its friendly atmosphere and strong sense of community. Residents enjoy bay-to-beach living, with easy access to Sarasota Bay, the Intracoastal Waterway, pristine Gulf beaches, a community boat ramp, kayaking, fishing, and renowned waterfront dining and boutique shopping—all within walking or golf-cart distance. Begin your mornings with peaceful bayfront sunrises and end your evenings with spectacular Gulf sunsets just moments away. This is a rare opportunity to own a fully updated, move-in- ready island retreat in one of Longboat Key’s most treasured neighborhoods, with convenient access to Sarasota’s world-class arts, dining, and entertainment. Schedule your private showing today and experience island living at its finest.

5 Beds ⋅ 4 Baths ⋅ Longbeach On Longboat Key SubDv. ⋅ 34228 Zip Code

Discover coastal tranquility and timeless island charm in this beautifully renovated five- bedroom, three and 1/2 bath residence nestled in the highly sought-after Longbeach Village community at the north end of Longboat Key. Offering over 2,700 square feet of thoughtfully redesigned living space, this impressive two-story home seamlessly blends classic character with modern luxury. The designer kitchen is a chef's dream and showcases quartz countertops, custom cabinetry, newer appliances, and updated flooring. The entire first floor has been fully updated, featuring new electrical, drywall, stylish interior doors, and reimagined spa-like bathrooms. Additional upgrades include impact-rated French entry doors, a new impact-rated foyer door, two new HVAC systems, a tankless water heater, and a new pool pump. Upstairs, soaring ceilings and abundant natural light create an airy, welcoming ambiance. Step outside to your private tropical oasis, where a resort-style pool and spa invite you to swim, relax, or entertain in style. Lush landscaping, a fully fenced yard, an upper balcony with serene views, and a generous covered poolside deck provide multiple spaces to unwind and enjoy the Florida lifestyle. Longbeach Village is a historic and vibrant bayfront community celebrated for its friendly atmosphere and strong sense of community. Residents enjoy bay-to-beach living, with easy access to Sarasota Bay, the Intracoastal Waterway, pristine Gulf beaches, a community boat ramp, kayaking, fishing, and renowned waterfront dining and boutique shopping—all within walking or golf-cart distance. Begin your mornings with peaceful bayfront sunrises and end your evenings with spectacular Gulf sunsets just moments away. This is a rare opportunity to own a fully updated, move-in- ready island retreat in one of Longboat Key’s most treasured neighborhoods, with convenient access to Sarasota’s world-class arts, dining, and entertainment. Schedule your private showing today and experience island living at its finest.

580 Russell Street, Longboat Key

3030 Grand Bay Boulevard Unit 312, Longboat Key

$910,000

Located in the Grand Bay community on Longboat Key, this spacious 3BR residence offers stunning views and desirable extras, including 2 conveniently located parking spaces. The pet friendly community allows up to 2 large dogs. The home features luxury vinyl flooring and neutral tones throughout, with floor-to-ceiling windows and plantation shutters that let in natural light. Elevated ceilings and accent lighting create an open, airy feel, while you enjoy views of Harbourside Golf Course, Sarasota Bay, and the downtown skyline from the expansive wraparound terrace that is perfect for entertaining or relaxing. The updated kitchen includes white cabinetry, Corian countertops, tile backsplash, stainless steel appliances, including a Sub-Zero refrigerator, and a central island. The living room/dining room offers ample space for a formal dining room table and large seating area. The primary suite is a private retreat, with access to the terrace and newly enhanced sightlines from the bedroom showcasing beautiful views of the Longboat Key Club golf course and Sarasota Bay. The primary bath features dual vanities, a walk-in shower, and a spa tub. The large custom closet is thoughtfully designed for ample storage. A full-size laundry room adds convenience. Grand Bay offers resort-style amenities including 24-hour gated security, a clubhouse with a library and game room, fitness center, 2 Har-Tru tennis courts, 2 heated pools, and a spa. Residents also enjoy deeded beach access through the Bay Isles Beach Club, just a short bike ride away. This private beach offers a peaceful, uncrowded environment, with a beachside pavilion, restrooms, and showers. Additionally, for those seeking more exclusive amenities, the optional Longboat Key Club provides access to luxury services, including golf, fine dining, a full-service spa, and fitness facilities.

3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Located in the Grand Bay community on Longboat Key, this spacious 3BR residence offers stunning views and desirable extras, including 2 conveniently located parking spaces. The pet friendly community allows up to 2 large dogs. The home features luxury vinyl flooring and neutral tones throughout, with floor-to-ceiling windows and plantation shutters that let in natural light. Elevated ceilings and accent lighting create an open, airy feel, while you enjoy views of Harbourside Golf Course, Sarasota Bay, and the downtown skyline from the expansive wraparound terrace that is perfect for entertaining or relaxing. The updated kitchen includes white cabinetry, Corian countertops, tile backsplash, stainless steel appliances, including a Sub-Zero refrigerator, and a central island. The living room/dining room offers ample space for a formal dining room table and large seating area. The primary suite is a private retreat, with access to the terrace and newly enhanced sightlines from the bedroom showcasing beautiful views of the Longboat Key Club golf course and Sarasota Bay. The primary bath features dual vanities, a walk-in shower, and a spa tub. The large custom closet is thoughtfully designed for ample storage. A full-size laundry room adds convenience. Grand Bay offers resort-style amenities including 24-hour gated security, a clubhouse with a library and game room, fitness center, 2 Har-Tru tennis courts, 2 heated pools, and a spa. Residents also enjoy deeded beach access through the Bay Isles Beach Club, just a short bike ride away. This private beach offers a peaceful, uncrowded environment, with a beachside pavilion, restrooms, and showers. Additionally, for those seeking more exclusive amenities, the optional Longboat Key Club provides access to luxury services, including golf, fine dining, a full-service spa, and fitness facilities.

3030 Grand Bay Boulevard Unit 312, Longboat Key

2013 Harbour Links Drive Unit 2013, Longboat Key

$905,000

Step into easy, worry-free condo living behind the double gates of Bay Isles. Set within an intimate community of just 20 residences, this fully furnished home is a rare find—showing no water or storm damage from recent storms. Seller recently updated HVAC system as well. Relax on your oversized screened lanai with peaceful golf course views and western skies that glow at sunset. The spacious primary suite opens directly to the lanai, while the guest bedroom is also en suite for privacy and comfort. A flexible family room and formal living area provide plenty of space for work, hobbies, or quiet relaxation. The private one-car garage and community-maintained elevator offer effortless access to the second-floor living area. Inside, the updated kitchen opens to a grilling patio, and the soaring ceilings in the living room create a bright, airy setting for entertaining family and friends. Ideally located on the south end of Longboat Key, this home is just minutes from St. Armands Circle, where dining, shopping, and coastal charm come together. Downtown Sarasota is only a short drive away, offering world-class restaurants, theaters, and boutique shopping. As a Bay Isles resident, you’ll enjoy exclusive membership to the Bay Isles Beach Club—boasting private access to the island’s sugary white sands and sparkling aqua waters. Additional membership opportunities are available at the Longboat Key Club, offering championship golf, tennis, spa, dining, and resort amenities.

2 Beds ⋅ 3 Baths ⋅ Harbour Links SubDv. ⋅ 34228 Zip Code

Step into easy, worry-free condo living behind the double gates of Bay Isles. Set within an intimate community of just 20 residences, this fully furnished home is a rare find—showing no water or storm damage from recent storms. Seller recently updated HVAC system as well. Relax on your oversized screened lanai with peaceful golf course views and western skies that glow at sunset. The spacious primary suite opens directly to the lanai, while the guest bedroom is also en suite for privacy and comfort. A flexible family room and formal living area provide plenty of space for work, hobbies, or quiet relaxation. The private one-car garage and community-maintained elevator offer effortless access to the second-floor living area. Inside, the updated kitchen opens to a grilling patio, and the soaring ceilings in the living room create a bright, airy setting for entertaining family and friends. Ideally located on the south end of Longboat Key, this home is just minutes from St. Armands Circle, where dining, shopping, and coastal charm come together. Downtown Sarasota is only a short drive away, offering world-class restaurants, theaters, and boutique shopping. As a Bay Isles resident, you’ll enjoy exclusive membership to the Bay Isles Beach Club—boasting private access to the island’s sugary white sands and sparkling aqua waters. Additional membership opportunities are available at the Longboat Key Club, offering championship golf, tennis, spa, dining, and resort amenities.

2013 Harbour Links Drive Unit 2013, Longboat Key

1211 Gulf Of Mexico Drive Unit 109, Longboat Key

$900,000

Virtually Staged. Experience beachfront living at its finest at The Promenade on Longboat Key. This beautifully positioned residence showcases sweeping Gulf Views expansive terraces, and a seamless connection between indoor and outdoor living. Floor-to-ceiling windows fill the home with natural light while framing spectacular sunsets, pristine beaches and lush tropical surroundings. Thoughtfully designed with custom woodwork and an open , flowing layout, the residence offers exceptional comfort and flexibility. The kitchen enjoys water views and a unique connection to celebrated culinary icon, Marcella Hazan. Often called "the godmother of Italian cuisine', her award-winning documentary premiered at the Sarasota Film Festival! Residents enjoy resort-style amenities including concierge services, a staffed gatehouse, over-sized heated pool and spa, tennis courts, men's & women's fitness facilities, the Sunset and Sunrise club rooms, beachside gathering areas and direct access to the Gulf. Ideally located on the coveted south end of Longboat Key, The Promenade offers convenient access to St Armands Circle, downtown Sarasota , premier golf, dining, shopping, arts and cultural attractions. A rare opportunity to enjoy an exceptional beachfront lifestyle in one of Longboat's most sought after communities.

2 Beds ⋅ 2 Baths ⋅ Promenade SubDv. ⋅ 34228 Zip Code

Virtually Staged. Experience beachfront living at its finest at The Promenade on Longboat Key. This beautifully positioned residence showcases sweeping Gulf Views expansive terraces, and a seamless connection between indoor and outdoor living. Floor-to-ceiling windows fill the home with natural light while framing spectacular sunsets, pristine beaches and lush tropical surroundings. Thoughtfully designed with custom woodwork and an open , flowing layout, the residence offers exceptional comfort and flexibility. The kitchen enjoys water views and a unique connection to celebrated culinary icon, Marcella Hazan. Often called "the godmother of Italian cuisine', her award-winning documentary premiered at the Sarasota Film Festival! Residents enjoy resort-style amenities including concierge services, a staffed gatehouse, over-sized heated pool and spa, tennis courts, men's & women's fitness facilities, the Sunset and Sunrise club rooms, beachside gathering areas and direct access to the Gulf. Ideally located on the coveted south end of Longboat Key, The Promenade offers convenient access to St Armands Circle, downtown Sarasota , premier golf, dining, shopping, arts and cultural attractions. A rare opportunity to enjoy an exceptional beachfront lifestyle in one of Longboat's most sought after communities.

1211 Gulf Of Mexico Drive Unit 109, Longboat Key

1955 Gulf Of Mexico Dr Unit G6-311, Longboat Key

$900,000

Experience the coastal gulf front living lifestyle to its fullest, in this 3-bedroom 2 bath condo with views of the Gulf from inside as well as the 2 balconies. Make this your new oasis and enjoy the sunsets off one of your two separate balconies (one off the main living area and another private balcony for the primary bedroom). Start experiencing this 3-bedroom condo at Seaplace which is located on a pristine beach area of Longboat Key. There is an array of amenities across the 42 beautifully landscaped acres, including two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center and a new gulf front firepit area. The clubhouse offers a kitchen, library, fitness area and sauna. Additional features include playground, grilling areas, on-site management, and a 24-hour staffed gatehouse.

3 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code

Experience the coastal gulf front living lifestyle to its fullest, in this 3-bedroom 2 bath condo with views of the Gulf from inside as well as the 2 balconies. Make this your new oasis and enjoy the sunsets off one of your two separate balconies (one off the main living area and another private balcony for the primary bedroom). Start experiencing this 3-bedroom condo at Seaplace which is located on a pristine beach area of Longboat Key. There is an array of amenities across the 42 beautifully landscaped acres, including two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center and a new gulf front firepit area. The clubhouse offers a kitchen, library, fitness area and sauna. Additional features include playground, grilling areas, on-site management, and a 24-hour staffed gatehouse.

1955 Gulf Of Mexico Dr Unit G6-311, Longboat Key

5635 Gulf Of Mexico Drive Unit 202, Longboat Key

$900,000

Welcome to Sandpipers, a boutique Gulf-front condominium community on the desirable north end of Longboat Key. This well-maintained second-floor residence offers 2 bedrooms, 2 bathrooms, and 1,786 square feet of relaxed coastal living. The home has been meticulously cared for with classic finishes and a show-stopping view. Step onto the private, screened lanai and take in soothing Gulf breezes, the sound of the waves, and spectacular sunsets over the Gulf of Mexico. The expansive lanai creates an inviting indoor-outdoor living space, perfect for morning coffee or evening relaxation. Residents of the 10-unit Sandpipers community enjoy private beach access and a community pool. The residence is offered furnished, making an easy transition into island living. Conveniently located close to St. Armands Circle, downtown Sarasota, and the coastal charm of Anna Maria Island. This is a rare opportunity to own a spacious and thoughtfully laid-out Gulf-front condo in one of Longboat Key’s most desirable boutique communities. Schedule your private showing today.

2 Beds ⋅ 2 Baths ⋅ Longboat Sandpipers Condo SubDv. ⋅ 34228 Zip Code

Welcome to Sandpipers, a boutique Gulf-front condominium community on the desirable north end of Longboat Key. This well-maintained second-floor residence offers 2 bedrooms, 2 bathrooms, and 1,786 square feet of relaxed coastal living. The home has been meticulously cared for with classic finishes and a show-stopping view. Step onto the private, screened lanai and take in soothing Gulf breezes, the sound of the waves, and spectacular sunsets over the Gulf of Mexico. The expansive lanai creates an inviting indoor-outdoor living space, perfect for morning coffee or evening relaxation. Residents of the 10-unit Sandpipers community enjoy private beach access and a community pool. The residence is offered furnished, making an easy transition into island living. Conveniently located close to St. Armands Circle, downtown Sarasota, and the coastal charm of Anna Maria Island. This is a rare opportunity to own a spacious and thoughtfully laid-out Gulf-front condo in one of Longboat Key’s most desirable boutique communities. Schedule your private showing today.

5635 Gulf Of Mexico Drive Unit 202, Longboat Key

$900,000

One or more photo(s) has been virtually staged. In the highly sought-after Longbeach community of Longboat Key, this .34+ acre waterfront parcel represents exceptional land value and future potential. Offering 78 feet of waterfront frontage and an impressive 192-foot depth, the property provides the scale and flexibility rarely available on the island today. Positioned on the Manatee County side with direct, no-bridge boating access to the Intracoastal Waterway, Sarasota Bay, and the Gulf of America, it presents a premier opportunity to build, expand, or invest—with an existing 1935 cottage already in place and VERY LIVABLE and adorable AS IT IS! Enjoy the luxury of a short walk to the beach, no HOA fees, and flexible rental terms with a one-month minimum allowed up to 12 times annually. RSF-6 zoning (Single-Family Medium-High Density) allows up to six units an acre (buyer to verify), opening the door to a primary residence with guest house, pool, and spa; and more! An existing dock (currently damaged and not usable as is) already has water and electric in place, with neighboring boats ranging between approximately 20-25 feet or larger in length; and ample room for a large lap pool and expansive outdoor entertaining. Over $100,000 in capital improvements include a shingle roof (2023), and extensive interior updates completed in 2025 following storm remediation, including all new flooring, paint, cabinetry, and drywall. Additional upgrades include a new 2.5-ton AC system (2024), electrical improvements with a 200-amp panel and grounding, water heater (2025), hurricane impact windows in most rooms, including the primary bedroom, kitchen, both bathrooms, and living room, a sizable upgrade to the home. Private irrigation well, providing peace of mind, long-term efficiency and conveniences of moving right in to enjoy this exceptional home and property! Offering two bedrooms, two bathrooms, and approximately 1,180 square feet, the home retains timeless island character with original cypress walls and ceilings, abundant windows, and a wood-burning fireplace that anchors the living space. A standout feature is the 15x33 rear-facing covered and screened lanai, providing approximately 510 square feet of under-roof outdoor living with pitched ceilings, fans, sun shades, and fully pocketing sliding glass doors, with the flexibility to incorporate this space into additional interior living if desired. The updated half-galley kitchen features shaker wood cabinetry, soft-close drawers, light quartz countertops, an LG stainless steel appliance package, deep stainless sink, pull-outs, and lazy Susan, all overlooking the front stoop and lawn. The spacious primary ensuite measures approximately 10x22 and includes room for seating or office use, dual sinks, his-and-hers closets, and a shower/tub combination. A shared full bath offers inlaid tile flooring and a walk-in shower with marble step. Wood flooring runs throughout with tile in the bathrooms, offering NO carpeting. Additional features include a shell and paver driveway, French front door, expansive fully pocketed sliding glass doors, gutters, fenced yard, and a one-car carport (that houses the washer, dryer and hot water heater) One of the last remaining original cottages in the Whitney Beach / LongBeach area, this property offers a compelling opportunity to restore historic charm, reimagine the footprint, or create a refined waterfront estate defined by location, land, boating, beach access, flexibility, and vision

Long Beach SubDv. ⋅ 34228 Zip Code

One or more photo(s) has been virtually staged. In the highly sought-after Longbeach community of Longboat Key, this .34+ acre waterfront parcel represents exceptional land value and future potential. Offering 78 feet of waterfront frontage and an impressive 192-foot depth, the property provides the scale and flexibility rarely available on the island today. Positioned on the Manatee County side with direct, no-bridge boating access to the Intracoastal Waterway, Sarasota Bay, and the Gulf of America, it presents a premier opportunity to build, expand, or invest—with an existing 1935 cottage already in place and VERY LIVABLE and adorable AS IT IS! Enjoy the luxury of a short walk to the beach, no HOA fees, and flexible rental terms with a one-month minimum allowed up to 12 times annually. RSF-6 zoning (Single-Family Medium-High Density) allows up to six units an acre (buyer to verify), opening the door to a primary residence with guest house, pool, and spa; and more! An existing dock (currently damaged and not usable as is) already has water and electric in place, with neighboring boats ranging between approximately 20-25 feet or larger in length; and ample room for a large lap pool and expansive outdoor entertaining. Over $100,000 in capital improvements include a shingle roof (2023), and extensive interior updates completed in 2025 following storm remediation, including all new flooring, paint, cabinetry, and drywall. Additional upgrades include a new 2.5-ton AC system (2024), electrical improvements with a 200-amp panel and grounding, water heater (2025), hurricane impact windows in most rooms, including the primary bedroom, kitchen, both bathrooms, and living room, a sizable upgrade to the home. Private irrigation well, providing peace of mind, long-term efficiency and conveniences of moving right in to enjoy this exceptional home and property! Offering two bedrooms, two bathrooms, and approximately 1,180 square feet, the home retains timeless island character with original cypress walls and ceilings, abundant windows, and a wood-burning fireplace that anchors the living space. A standout feature is the 15x33 rear-facing covered and screened lanai, providing approximately 510 square feet of under-roof outdoor living with pitched ceilings, fans, sun shades, and fully pocketing sliding glass doors, with the flexibility to incorporate this space into additional interior living if desired. The updated half-galley kitchen features shaker wood cabinetry, soft-close drawers, light quartz countertops, an LG stainless steel appliance package, deep stainless sink, pull-outs, and lazy Susan, all overlooking the front stoop and lawn. The spacious primary ensuite measures approximately 10x22 and includes room for seating or office use, dual sinks, his-and-hers closets, and a shower/tub combination. A shared full bath offers inlaid tile flooring and a walk-in shower with marble step. Wood flooring runs throughout with tile in the bathrooms, offering NO carpeting. Additional features include a shell and paver driveway, French front door, expansive fully pocketed sliding glass doors, gutters, fenced yard, and a one-car carport (that houses the washer, dryer and hot water heater) One of the last remaining original cottages in the Whitney Beach / LongBeach area, this property offers a compelling opportunity to restore historic charm, reimagine the footprint, or create a refined waterfront estate defined by location, land, boating, beach access, flexibility, and vision

6841 Longboat Drive S, Longboat Key

$900,000

Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.

3 Beds ⋅ 4 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code

Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.

552 Juan Anasco Drive, Longboat Key

$900,000

It’s all about location. Close to everything. Away from it all. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. Surrounded by tropical landscaping, this home makes the most of its spaciously designed 2,267 square feet with open-plan living, three bedrooms, two full baths and a half-bath, 26-foot balcony, garage, and ample storage space that are well elevated. The interior creates feelings of tranquility and hospitality throughout. The main living space enjoys abundant natural light and views from 9-foot sliding glass doors. The kitchen opens to the dining and living areas for effortless entertainment with added dining alfresco on the balcony or at the pool. The primary bedroom is generous with en-suite bath offering peace in a soaking tub and spacious dual vanities. Completing the primary suite is a spatial walk-in closet. Two guest wings each with a bath and walk-in closets for added storage extend family and friends every comfort. It’s all about connectivity. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport’s soaring success added 30 flights in 2024 and 2025, strong passenger growth, a new $72 million runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It’s all about investment. This home in The Bayou neighborhood of the planned community of Bay Isles could be your destination of choice. Residents enjoy access to the private Bay Isles Beach Club, a Gulf-front retreat with cabanas, picnic areas, grills, and beach is yours to enjoy the sand and world-class sunsets. There are also responsive management and maintenance staff, making where home and away share the same address. Membership is available for Longboat Key Club’s 45 holes of golf, Tennis Garden 20 Har-Tru courts, Moorings Marina 291 deepwater slips for vessels up to 150 feet, wellness spa and five unique restaurants. Not to be overlooked is proximity to St. Armands Circle, an unforgettable destination with over 130 boutiques, galleries and restaurants surrounding a central park. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025.

3 Beds ⋅ 3 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

It’s all about location. Close to everything. Away from it all. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. Surrounded by tropical landscaping, this home makes the most of its spaciously designed 2,267 square feet with open-plan living, three bedrooms, two full baths and a half-bath, 26-foot balcony, garage, and ample storage space that are well elevated. The interior creates feelings of tranquility and hospitality throughout. The main living space enjoys abundant natural light and views from 9-foot sliding glass doors. The kitchen opens to the dining and living areas for effortless entertainment with added dining alfresco on the balcony or at the pool. The primary bedroom is generous with en-suite bath offering peace in a soaking tub and spacious dual vanities. Completing the primary suite is a spatial walk-in closet. Two guest wings each with a bath and walk-in closets for added storage extend family and friends every comfort. It’s all about connectivity. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport’s soaring success added 30 flights in 2024 and 2025, strong passenger growth, a new $72 million runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It’s all about investment. This home in The Bayou neighborhood of the planned community of Bay Isles could be your destination of choice. Residents enjoy access to the private Bay Isles Beach Club, a Gulf-front retreat with cabanas, picnic areas, grills, and beach is yours to enjoy the sand and world-class sunsets. There are also responsive management and maintenance staff, making where home and away share the same address. Membership is available for Longboat Key Club’s 45 holes of golf, Tennis Garden 20 Har-Tru courts, Moorings Marina 291 deepwater slips for vessels up to 150 feet, wellness spa and five unique restaurants. Not to be overlooked is proximity to St. Armands Circle, an unforgettable destination with over 130 boutiques, galleries and restaurants surrounding a central park. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025.

3291 Bayou Road, Longboat Key

$900,000

One or more photo(s) has been virtually staged. Rarely does a property offer this much land, waterfront, and location value within the cherished Longbeach community of Longboat Key. Located on the desirable Manatee County side of the island, this original 1935 coastal cottage sits on an oversized .34+ acre waterfront lot with approximately 78 feet of frontage and an impressive 192-foot depth—dimensions increasingly difficult to find on Longboat Key. Enjoy direct, bridge-free boating to the Intracoastal Waterway, Sarasota Bay, and the Gulf of America, making it an exceptional opportunity for boaters, investors, or those looking to build a future waterfront estate. All just moments from the beach and within walking distance of the charm and character of Longbeach Village. Enjoy a short walk to the beach, no HOA fees, and flexible rentals with one-month minimums allowed up to 12 times per year. RSF-6 zoning (buyer to verify) allows up to six units per acre, offering potential for a primary home with guest house, pool, and spa. An existing dock (currently damaged) already has water and electric, and the lot provides ample space for a large lap pool and outdoor entertaining. Over $100,000 in capital improvements include a shingle roof (2023), and extensive interior updates completed in 2025 following storm remediation, including all new flooring, paint, cabinetry, and drywall. Additional upgrades include a new 2.5-ton AC system (2024), electrical improvements with a 200-amp panel and grounding, water heater (2025), hurricane impact windows in most rooms, including the primary bedroom, kitchen, both bathrooms, and living room, a sizable upgrade to the home. Private irrigation well, providing peace of mind, long-term efficiency and conveniences of moving right in to enjoy this exceptional home and property! Offering two bedrooms, two bathrooms, and approximately 1,180 square feet, the home retains timeless island character with original cypress walls and ceilings, abundant windows, and a wood-burning fireplace that anchors the living space. A standout feature is the 15x33 rear-facing covered and screened lanai, providing approximately 510 square feet of under-roof outdoor living with pitched ceilings, fans, sun shades, and fully pocketing sliding glass doors, with the flexibility to incorporate this space into additional interior living if desired. The updated half-galley kitchen features shaker wood cabinetry, soft-close drawers, light quartz countertops, an LG stainless steel appliance package, deep stainless sink, pull-outs, and lazy Susan, all overlooking the front stoop and lawn. The spacious primary ensuite measures approximately 10x22 and includes room for seating or office use, dual sinks, his-and-hers closets, and a shower/tub combination. A shared full bath offers inlaid tile flooring and a walk-in shower with marble step. Wood flooring runs throughout with tile in the bathrooms, offering NO carpeting. Additional features include a shell and paver driveway, French front door, expansive fully pocketed sliding glass doors, gutters, fenced yard, and a one-car carport (that houses the washer, dryer and hot water heater). One of the last remaining original cottages in the Whitney Beach / LongBeach area, this property offers a compelling opportunity to restore historic charm, reimagine the footprint, or create a refined waterfront estate defined by location, land, boating, beach access, flexibility, and vision. SELLER financing terms available upon request.

2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code

One or more photo(s) has been virtually staged. Rarely does a property offer this much land, waterfront, and location value within the cherished Longbeach community of Longboat Key. Located on the desirable Manatee County side of the island, this original 1935 coastal cottage sits on an oversized .34+ acre waterfront lot with approximately 78 feet of frontage and an impressive 192-foot depth—dimensions increasingly difficult to find on Longboat Key. Enjoy direct, bridge-free boating to the Intracoastal Waterway, Sarasota Bay, and the Gulf of America, making it an exceptional opportunity for boaters, investors, or those looking to build a future waterfront estate. All just moments from the beach and within walking distance of the charm and character of Longbeach Village. Enjoy a short walk to the beach, no HOA fees, and flexible rentals with one-month minimums allowed up to 12 times per year. RSF-6 zoning (buyer to verify) allows up to six units per acre, offering potential for a primary home with guest house, pool, and spa. An existing dock (currently damaged) already has water and electric, and the lot provides ample space for a large lap pool and outdoor entertaining. Over $100,000 in capital improvements include a shingle roof (2023), and extensive interior updates completed in 2025 following storm remediation, including all new flooring, paint, cabinetry, and drywall. Additional upgrades include a new 2.5-ton AC system (2024), electrical improvements with a 200-amp panel and grounding, water heater (2025), hurricane impact windows in most rooms, including the primary bedroom, kitchen, both bathrooms, and living room, a sizable upgrade to the home. Private irrigation well, providing peace of mind, long-term efficiency and conveniences of moving right in to enjoy this exceptional home and property! Offering two bedrooms, two bathrooms, and approximately 1,180 square feet, the home retains timeless island character with original cypress walls and ceilings, abundant windows, and a wood-burning fireplace that anchors the living space. A standout feature is the 15x33 rear-facing covered and screened lanai, providing approximately 510 square feet of under-roof outdoor living with pitched ceilings, fans, sun shades, and fully pocketing sliding glass doors, with the flexibility to incorporate this space into additional interior living if desired. The updated half-galley kitchen features shaker wood cabinetry, soft-close drawers, light quartz countertops, an LG stainless steel appliance package, deep stainless sink, pull-outs, and lazy Susan, all overlooking the front stoop and lawn. The spacious primary ensuite measures approximately 10x22 and includes room for seating or office use, dual sinks, his-and-hers closets, and a shower/tub combination. A shared full bath offers inlaid tile flooring and a walk-in shower with marble step. Wood flooring runs throughout with tile in the bathrooms, offering NO carpeting. Additional features include a shell and paver driveway, French front door, expansive fully pocketed sliding glass doors, gutters, fenced yard, and a one-car carport (that houses the washer, dryer and hot water heater). One of the last remaining original cottages in the Whitney Beach / LongBeach area, this property offers a compelling opportunity to restore historic charm, reimagine the footprint, or create a refined waterfront estate defined by location, land, boating, beach access, flexibility, and vision. SELLER financing terms available upon request.

6841 Longboat Drive S, Longboat Key

1050 Longboat Club Road Unit 301, Longboat Key

$900,000

Huge price reduction now under $1mm for direct 180 degree gulf front! Imagine waking up every morning to the sound of gentle waves and stepping onto your balcony to enjoy uninterrupted, straight-on Gulf views—this rarely available 01-stack residence delivers beachfront living exactly the way it should be. Perfectly positioned behind the private gates of the Longboat Key Club and nestled between the iconic Resort at Longboat Key Club and the spectacular new St. Regis Resort, Unit 301 at Privateer North is an ISLAND BEAUTY designed to delight the most discerning buyers. Picture yourself relaxing in the living room or primary suite, both opening to separate private balconies where you can sip your morning coffee, feel the warm Gulf breeze, and watch dolphins glide by almost daily. Then finish the day with some of the best sunsets in the state! With a layout tailored for coastal comfort, this home invites you to settle into a lifestyle where every day feels like a vacation. Residents enjoy a refined, resort-style environment with a secure lobby, on-site manager, tennis and pickleball courts, a heated pool and spa, well-equipped fitness center, and beautifully refurbished amenities. Everything has been updated: lobby, hallways, elevators, social room, and enhanced beachfront landscaping—creating an unmistakably fresh and upscale atmosphere. For golf, tennis, and pickleball enthusiasts, optional Longboat Key Club membership unlocks two championship golf courses (27 holes at Harbourside and 18 holes at Links on Longboat), 25 Har-Tru tennis courts, 8 new pickleball courts, professional instruction, and a top-tier pro shop. And when you venture beyond the gates, you’re moments from 10 miles of pristine beaches, boating, fishing, fine and casual dining, boutique shopping at the famous St Armands Circle, and Sarasota’s world-class cultural offerings just over the Ringling Bridge. Imagine living where every day ends with a beachfront sunset and every moment feels effortless—this is Longboat Key luxury at its finest, and it can be yours. Call for your private tour!

2 Beds ⋅ 2 Baths ⋅ Privateer North SubDv. ⋅ 34228 Zip Code

Huge price reduction now under $1mm for direct 180 degree gulf front! Imagine waking up every morning to the sound of gentle waves and stepping onto your balcony to enjoy uninterrupted, straight-on Gulf views—this rarely available 01-stack residence delivers beachfront living exactly the way it should be. Perfectly positioned behind the private gates of the Longboat Key Club and nestled between the iconic Resort at Longboat Key Club and the spectacular new St. Regis Resort, Unit 301 at Privateer North is an ISLAND BEAUTY designed to delight the most discerning buyers. Picture yourself relaxing in the living room or primary suite, both opening to separate private balconies where you can sip your morning coffee, feel the warm Gulf breeze, and watch dolphins glide by almost daily. Then finish the day with some of the best sunsets in the state! With a layout tailored for coastal comfort, this home invites you to settle into a lifestyle where every day feels like a vacation. Residents enjoy a refined, resort-style environment with a secure lobby, on-site manager, tennis and pickleball courts, a heated pool and spa, well-equipped fitness center, and beautifully refurbished amenities. Everything has been updated: lobby, hallways, elevators, social room, and enhanced beachfront landscaping—creating an unmistakably fresh and upscale atmosphere. For golf, tennis, and pickleball enthusiasts, optional Longboat Key Club membership unlocks two championship golf courses (27 holes at Harbourside and 18 holes at Links on Longboat), 25 Har-Tru tennis courts, 8 new pickleball courts, professional instruction, and a top-tier pro shop. And when you venture beyond the gates, you’re moments from 10 miles of pristine beaches, boating, fishing, fine and casual dining, boutique shopping at the famous St Armands Circle, and Sarasota’s world-class cultural offerings just over the Ringling Bridge. Imagine living where every day ends with a beachfront sunset and every moment feels effortless—this is Longboat Key luxury at its finest, and it can be yours. Call for your private tour!

1050 Longboat Club Road Unit 301, Longboat Key

2721 Gulf Of Mexico Drive Unit 408, Longboat Key

$900,000

Rare Gulf-Front Opportunity! This is the only listing currently available at The Beachcomber on Longboat Key. Perfectly positioned on the 4th floor, this corner residence is filled with natural light from multiple windows and offers unobstructed, direct Gulf-front views. The beautifully updated two-bedroom, two-bath condominium provides the ultimate in coastal living, with the flexibility of weekly rentals and an on-site rental office—allowing you to occupy, rent, or enjoy the best of both worlds. The thoughtfully designed floor plan places both bedrooms and the living room along the Gulf side, showcasing stunning water views. Step onto the expansive balcony, which spans the full width of the unit, and enjoy breathtaking sunsets over the Gulf of Mexico each evening. The open-concept kitchen, living, and dining areas have been tastefully renovated, featuring modern finishes that complement the bright, airy interior. Both bathrooms have also been stylishly updated. Enjoy the convenience of Gulf-side amenities—no need to cross Gulf of Mexico Drive to enjoy the recently resurfaced pool area which offers all-new loungers, seating, and upgraded pool equipment for relaxation any time of day. The community has also undergone beautiful exterior enhancements, including new landscaping and freshly installed pavers at the entrance of the building, creating a modern, welcoming feel. Ideally located away from the main road, this residence provides peace and privacy while being just steps from Publix, CVS, fitness centers, banks, public tennis courts, the library, and Town Hall. You’re also just minutes from St. Armands Circle, known for its fine dining and boutique shopping, and a short drive to downtown Sarasota and its cultural attractions. For added convenience, a private storage locker is included on the first floor. This exceptional property offers a true Longboat Key lifestyle—elegant, convenient, and steps from the sand.

2 Beds ⋅ 2 Baths ⋅ Beachcomber Apts SubDv. ⋅ 34228 Zip Code

Rare Gulf-Front Opportunity! This is the only listing currently available at The Beachcomber on Longboat Key. Perfectly positioned on the 4th floor, this corner residence is filled with natural light from multiple windows and offers unobstructed, direct Gulf-front views. The beautifully updated two-bedroom, two-bath condominium provides the ultimate in coastal living, with the flexibility of weekly rentals and an on-site rental office—allowing you to occupy, rent, or enjoy the best of both worlds. The thoughtfully designed floor plan places both bedrooms and the living room along the Gulf side, showcasing stunning water views. Step onto the expansive balcony, which spans the full width of the unit, and enjoy breathtaking sunsets over the Gulf of Mexico each evening. The open-concept kitchen, living, and dining areas have been tastefully renovated, featuring modern finishes that complement the bright, airy interior. Both bathrooms have also been stylishly updated. Enjoy the convenience of Gulf-side amenities—no need to cross Gulf of Mexico Drive to enjoy the recently resurfaced pool area which offers all-new loungers, seating, and upgraded pool equipment for relaxation any time of day. The community has also undergone beautiful exterior enhancements, including new landscaping and freshly installed pavers at the entrance of the building, creating a modern, welcoming feel. Ideally located away from the main road, this residence provides peace and privacy while being just steps from Publix, CVS, fitness centers, banks, public tennis courts, the library, and Town Hall. You’re also just minutes from St. Armands Circle, known for its fine dining and boutique shopping, and a short drive to downtown Sarasota and its cultural attractions. For added convenience, a private storage locker is included on the first floor. This exceptional property offers a true Longboat Key lifestyle—elegant, convenient, and steps from the sand.

2721 Gulf Of Mexico Drive Unit 408, Longboat Key

3080 Grand Bay Boulevard Unit 516, Longboat Key

$900,000

One or more photo(s) has been virtually staged. Perfectly positioned within the sought-after Grand Bay community, this Aruba residence blends convenient design, refined comfort, and a premier Longboat Key lifestyle. Overlooking Sarasota Bay, the golf course, and the downtown skyline, this two-bedroom home offers a combination of privacy, panoramic vistas, and recent designer enhancements. Set behind the gates of Bay Isles, this corner residence is bathed in natural light from expansive floor-to-ceiling glass doors and windows. The open great room serves as the heart of the home, offering a flexible space for entertaining and relaxing, framed by captivating views of the bay and city beyond. A wraparound balcony extends the living area outdoors, ideal for morning coffee, al fresco dining, or evening sunsets. The 2025 kitchen renovation introduced a complete reimagining of this important space—featuring custom cabinetry, removal of overhead soffits for added height and openness, upgraded plumbing, new LED and under-cabinet lighting, and all-new hardwood flooring carried throughout the residence. The modernized kitchen blends timeless finishes with functional elegance, offering ample workspace and stylish appeal for both everyday use and entertaining. The primary suite is a tranquil retreat, capturing water views and featuring an en-suite bath with dual sinks, a soaking tub, and a separate walk-in shower. A spacious walk-in closet provides exceptional storage. The guest bedroom offers options to act as an office or den, allowing effortless flexibility for visiting guests. Additional features also include two under-building parking spaces and a private storage locker. Within the secure and beautifully maintained Grand Bay community, residents enjoy an array of luxury amenities, including two resort-style swimming pools and spas, fully equipped fitness center, and clubhouse, tennis courts and pickleball, 24-hour guarded gate entry and on-site management. Grand Bay’s location behind the Bay Isles gates grants owners private beach access to the Gulf of Mexico through the Bay Isles Beach Club. The Longboat Key Club golf course and marina are nearby, offering exceptional recreation options. Beyond the gates, you’re moments from St. Armands Circle’s boutiques and fine dining, the vibrant arts and theater scene of downtown Sarasota, and world-renowned beaches along Longboat and Lido Key. Whether you’re seeking a seasonal escape or a year-round residence, this Grand Bay condominium captures the essence of coastal sophistication—where modern updates meet the serenity of bayfront living.

2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

One or more photo(s) has been virtually staged. Perfectly positioned within the sought-after Grand Bay community, this Aruba residence blends convenient design, refined comfort, and a premier Longboat Key lifestyle. Overlooking Sarasota Bay, the golf course, and the downtown skyline, this two-bedroom home offers a combination of privacy, panoramic vistas, and recent designer enhancements. Set behind the gates of Bay Isles, this corner residence is bathed in natural light from expansive floor-to-ceiling glass doors and windows. The open great room serves as the heart of the home, offering a flexible space for entertaining and relaxing, framed by captivating views of the bay and city beyond. A wraparound balcony extends the living area outdoors, ideal for morning coffee, al fresco dining, or evening sunsets. The 2025 kitchen renovation introduced a complete reimagining of this important space—featuring custom cabinetry, removal of overhead soffits for added height and openness, upgraded plumbing, new LED and under-cabinet lighting, and all-new hardwood flooring carried throughout the residence. The modernized kitchen blends timeless finishes with functional elegance, offering ample workspace and stylish appeal for both everyday use and entertaining. The primary suite is a tranquil retreat, capturing water views and featuring an en-suite bath with dual sinks, a soaking tub, and a separate walk-in shower. A spacious walk-in closet provides exceptional storage. The guest bedroom offers options to act as an office or den, allowing effortless flexibility for visiting guests. Additional features also include two under-building parking spaces and a private storage locker. Within the secure and beautifully maintained Grand Bay community, residents enjoy an array of luxury amenities, including two resort-style swimming pools and spas, fully equipped fitness center, and clubhouse, tennis courts and pickleball, 24-hour guarded gate entry and on-site management. Grand Bay’s location behind the Bay Isles gates grants owners private beach access to the Gulf of Mexico through the Bay Isles Beach Club. The Longboat Key Club golf course and marina are nearby, offering exceptional recreation options. Beyond the gates, you’re moments from St. Armands Circle’s boutiques and fine dining, the vibrant arts and theater scene of downtown Sarasota, and world-renowned beaches along Longboat and Lido Key. Whether you’re seeking a seasonal escape or a year-round residence, this Grand Bay condominium captures the essence of coastal sophistication—where modern updates meet the serenity of bayfront living.

3080 Grand Bay Boulevard Unit 516, Longboat Key

3465 Winding Oaks Drive Unit 33, Longboat Key

$900,000

This stunning three-bedroom, three-bath villa offers a serene waterfront retreat in the desirable Winding Oaks community of Longboat Key Club. With a spacious open floor plan spanning 2,608 Sf, the maintenance-free home is bathed in natural light and features vaulted ceilings that enhance its airy feel. The inviting living/dining room combo seamlessly connects to a screened-in back deck, perfect for enjoying picturesque water views. The kitchen is a chef’s dream, equipped with a gas range, large refrigerator with ice maker, built-in oven, custom wood cabinetry, and ample counter space for culinary creations. A cozy den adjacent to the kitchen provides a perfect gathering spot for family and friends. The thoughtfully designed layout ensures privacy among the three bedrooms, with one versatile space featuring a Murphy bed ideal for an office or guest room. Residents enjoy exclusive access to the Bay Isles Beach Club and 24-hour security, all while being conveniently located near shopping, dining, and the luxurious St. Regis Longboat Key Resort. Importantly, the villa at Winding Oaks has proven resilient, having not sustained any damage from recent hurricanes.

3 Beds ⋅ 3 Baths ⋅ Winding Oaks SubDv. ⋅ 34228 Zip Code

This stunning three-bedroom, three-bath villa offers a serene waterfront retreat in the desirable Winding Oaks community of Longboat Key Club. With a spacious open floor plan spanning 2,608 Sf, the maintenance-free home is bathed in natural light and features vaulted ceilings that enhance its airy feel. The inviting living/dining room combo seamlessly connects to a screened-in back deck, perfect for enjoying picturesque water views. The kitchen is a chef’s dream, equipped with a gas range, large refrigerator with ice maker, built-in oven, custom wood cabinetry, and ample counter space for culinary creations. A cozy den adjacent to the kitchen provides a perfect gathering spot for family and friends. The thoughtfully designed layout ensures privacy among the three bedrooms, with one versatile space featuring a Murphy bed ideal for an office or guest room. Residents enjoy exclusive access to the Bay Isles Beach Club and 24-hour security, all while being conveniently located near shopping, dining, and the luxurious St. Regis Longboat Key Resort. Importantly, the villa at Winding Oaks has proven resilient, having not sustained any damage from recent hurricanes.

3465 Winding Oaks Drive Unit 33, Longboat Key

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