$800,000 Welcome to Residence #103 at 1445 Gulf of Mexico Drive, located within the prestigious Players Club on Longboat Key. This exceptional 550-foot Gulf-front community offers an unparalleled coastal lifestyle, and this residence presents a rare opportunity—available for the first time in 37 years. Originally the building’s model home, this thoughtfully designed condominium combines timeless elegance with spacious comfort. This beautifully maintained residence features three bedrooms, two and a half baths. The third bedroom/den is complete with twin Murphy beds and built-in storage. The spacious living and dining area opens to a wall of sliding glass doors leading to an expansive 30-foot open-air balcony, where you will enjoy sweeping views of the Gulf of Mexico, overlooking the 70-foot heated saltwater swimming pool, spa, lush tropical landscaping, and breathtaking sunsets. Just steps from the pristine beach, this outdoor retreat invites you to relax, read, listen to the waves, and savor spectacular evening skies. Inside, the home offers a seamless blend of style and functionality. The spacious primary suite features sliding glass doors to the balcony, a generous walk-in closet, and a split en-suite bath with dual vanities, a spa-like soaking tub and shower, and a large window that fills the space with natural light. The second en-suite bedroom, privately positioned off the front hallway, is generously sized, offers abundant natural light, and includes a large walk-in closet—perfect for guests. Additional conveniences include a powder room, in-unit laundry, interior storage, and a private storage closet just outside the front door. The residence also includes assigned under-building parking and access to bike storage. Residents of Players Club enjoy resort-style amenities, including a newly renovated clubhouse with a state-of-the-art fitness center, library, catering kitchen, and inviting indoor and outdoor social spaces. Four Har-Tru tennis courts, pickleball, a putting green, beautifully maintained grounds, a security gate, and on-site management provide both luxury and peace of mind. Ideally situated on the desirable south end of Longboat Key, this community is just minutes from Publix, the renowned St. Regis Longboat Key Resort, the upscale boutiques and fine dining of St. Armands Circle, and the vibrant cultural attractions of downtown Sarasota. This is a rare opportunity to own a distinguished Gulf-front residence in one of Florida’s most sought-after coastal communities—where luxury, location, and lifestyle come together beautifully. 3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code Welcome to Residence #103 at 1445 Gulf of Mexico Drive, located within the prestigious Players Club on Longboat Key. This exceptional 550-foot Gulf-front community offers an unparalleled coastal lifestyle, and this residence presents a rare opportunity—available for the first time in 37 years. Originally the building’s model home, this thoughtfully designed condominium combines timeless elegance with spacious comfort. This beautifully maintained residence features three bedrooms, two and a half baths. The third bedroom/den is complete with twin Murphy beds and built-in storage. The spacious living and dining area opens to a wall of sliding glass doors leading to an expansive 30-foot open-air balcony, where you will enjoy sweeping views of the Gulf of Mexico, overlooking the 70-foot heated saltwater swimming pool, spa, lush tropical landscaping, and breathtaking sunsets. Just steps from the pristine beach, this outdoor retreat invites you to relax, read, listen to the waves, and savor spectacular evening skies. Inside, the home offers a seamless blend of style and functionality. The spacious primary suite features sliding glass doors to the balcony, a generous walk-in closet, and a split en-suite bath with dual vanities, a spa-like soaking tub and shower, and a large window that fills the space with natural light. The second en-suite bedroom, privately positioned off the front hallway, is generously sized, offers abundant natural light, and includes a large walk-in closet—perfect for guests. Additional conveniences include a powder room, in-unit laundry, interior storage, and a private storage closet just outside the front door. The residence also includes assigned under-building parking and access to bike storage. Residents of Players Club enjoy resort-style amenities, including a newly renovated clubhouse with a state-of-the-art fitness center, library, catering kitchen, and inviting indoor and outdoor social spaces. Four Har-Tru tennis courts, pickleball, a putting green, beautifully maintained grounds, a security gate, and on-site management provide both luxury and peace of mind. Ideally situated on the desirable south end of Longboat Key, this community is just minutes from Publix, the renowned St. Regis Longboat Key Resort, the upscale boutiques and fine dining of St. Armands Circle, and the vibrant cultural attractions of downtown Sarasota. This is a rare opportunity to own a distinguished Gulf-front residence in one of Florida’s most sought-after coastal communities—where luxury, location, and lifestyle come together beautifully. 1445 Gulf Of Mexico Drive Unit 103, Longboat Key
$800,000 Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony. The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street. Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports. Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value. 3 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv. ⋅ 34228 Zip Code Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony. The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street. Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports. Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value. 4234 Gulf Of Mexico Drive Unit G2, Longboat Key
$775,000 Welcome to this beautifully updated coastal retreat, where style, comfort, and functionality come together seamlessly. This light-filled residence features an open-concept layout with wide-plank tile flooring throughout, creating a clean, modern look that’s perfect for beachside living. The updated kitchen is both stylish and functional, showcasing granite countertops, custom cabinetry, stainless steel appliances, and a spacious breakfast bar—ideal for entertaining or casual dining. Relax and unwind in the spacious living area, which flows effortlessly to the screened lanai—perfect for enjoying morning coffee or evening breezes with partial Gulf views and lush tropical surroundings. The primary suite offers a serene escape with tasteful coastal décor and ample storage, while the guest bedroom is thoughtfully designed for comfort and privacy. The fully renovated bathroom features a walk-in glass-enclosed shower, modern tilework, and dual vanities for added convenience. Additional highlights include: In-unit washer & dryer Updated finishes throughout Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an impressive array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a well-equipped fitness center, and a clubhouse featuring a kitchen, library, and sauna. Additional amenities include a playground, community grills, on-site management, and a 24-hour staffed gatehouse for security. Enjoy breathtaking sunsets, peaceful walking paths, and a truly low-maintenance island lifestyle—all at an exceptional value. Schedule your private showing today! 2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code Welcome to this beautifully updated coastal retreat, where style, comfort, and functionality come together seamlessly. This light-filled residence features an open-concept layout with wide-plank tile flooring throughout, creating a clean, modern look that’s perfect for beachside living. The updated kitchen is both stylish and functional, showcasing granite countertops, custom cabinetry, stainless steel appliances, and a spacious breakfast bar—ideal for entertaining or casual dining. Relax and unwind in the spacious living area, which flows effortlessly to the screened lanai—perfect for enjoying morning coffee or evening breezes with partial Gulf views and lush tropical surroundings. The primary suite offers a serene escape with tasteful coastal décor and ample storage, while the guest bedroom is thoughtfully designed for comfort and privacy. The fully renovated bathroom features a walk-in glass-enclosed shower, modern tilework, and dual vanities for added convenience. Additional highlights include: In-unit washer & dryer Updated finishes throughout Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an impressive array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a well-equipped fitness center, and a clubhouse featuring a kitchen, library, and sauna. Additional amenities include a playground, community grills, on-site management, and a 24-hour staffed gatehouse for security. Enjoy breathtaking sunsets, peaceful walking paths, and a truly low-maintenance island lifestyle—all at an exceptional value. Schedule your private showing today! 1925 Gulf Of Mexico Drive Unit G8-303, Longboat Key
$775,000 Welcome to effortless coastal living in this beautifully maintained, fully furnished end-unit villa on Longboat Key. Offering nearly 2,400 square feet of thoughtfully designed living space, this exceptional residence combines the spaciousness and privacy of a single-family home with the convenience of maintenance-free living—all just moments from the Gulf's renowned white-sand beaches. From the moment you step inside, soaring vaulted ceilings, abundant natural light, and an open, airy floor plan create a warm and inviting atmosphere. Designed for both comfortable everyday living and effortless entertaining, the home offers multiple gathering spaces, including a formal living room with a charming wood-burning fireplace and expansive sliding glass doors that open to an impressive 740-square-foot private terrace overlooking peaceful pond views. The kitchen is both stylish and functional, featuring granite countertops, updated cabinetry, rich wood flooring, plantation shutters, and a skylight that fills the space with natural light. Recent upgrades, including a new roof and new air-conditioning system completed in 2025, provide added comfort and peace of mind. Adding to the home's unique character are two private atriums that bring the outdoors in, creating bright, tranquil spaces throughout the residence. A versatile office with a built-in Murphy bed offers the flexibility to easily serve as a fourth bedroom, while the spacious primary suite provides a relaxing retreat with comfortable accommodations for family and guests. Additional highlights include a private two-car garage with organized storage, a heated community pool and spa, and exclusive membership to the gated Bay Isles Beach Club, where residents enjoy private Gulf-front beach access and dedicated parking. Perfectly located near world-class beaches, boating, waterfront restaurants, boutique shopping, and the renowned Longboat Key Club's golf, tennis, pickleball, marina, and dining amenities, this residence places the very best of island living right at your doorstep. Beautifully furnished, impeccably maintained, and move-in ready, this is an exceptional opportunity to enjoy the relaxed elegance and coastal lifestyle that make Longboat Key one of Florida's most sought-after destinations. 3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code Welcome to effortless coastal living in this beautifully maintained, fully furnished end-unit villa on Longboat Key. Offering nearly 2,400 square feet of thoughtfully designed living space, this exceptional residence combines the spaciousness and privacy of a single-family home with the convenience of maintenance-free living—all just moments from the Gulf's renowned white-sand beaches. From the moment you step inside, soaring vaulted ceilings, abundant natural light, and an open, airy floor plan create a warm and inviting atmosphere. Designed for both comfortable everyday living and effortless entertaining, the home offers multiple gathering spaces, including a formal living room with a charming wood-burning fireplace and expansive sliding glass doors that open to an impressive 740-square-foot private terrace overlooking peaceful pond views. The kitchen is both stylish and functional, featuring granite countertops, updated cabinetry, rich wood flooring, plantation shutters, and a skylight that fills the space with natural light. Recent upgrades, including a new roof and new air-conditioning system completed in 2025, provide added comfort and peace of mind. Adding to the home's unique character are two private atriums that bring the outdoors in, creating bright, tranquil spaces throughout the residence. A versatile office with a built-in Murphy bed offers the flexibility to easily serve as a fourth bedroom, while the spacious primary suite provides a relaxing retreat with comfortable accommodations for family and guests. Additional highlights include a private two-car garage with organized storage, a heated community pool and spa, and exclusive membership to the gated Bay Isles Beach Club, where residents enjoy private Gulf-front beach access and dedicated parking. Perfectly located near world-class beaches, boating, waterfront restaurants, boutique shopping, and the renowned Longboat Key Club's golf, tennis, pickleball, marina, and dining amenities, this residence places the very best of island living right at your doorstep. Beautifully furnished, impeccably maintained, and move-in ready, this is an exceptional opportunity to enjoy the relaxed elegance and coastal lifestyle that make Longboat Key one of Florida's most sought-after destinations. 2326 Harbour Oaks Drive, Longboat Key
$775,000 Turnkey furnished and direct Gulf-front, this exceptional ground-floor residence at Turtle Crawl Inn on Longboat Key offers both effortless beachfront living and remarkable, documented rental performance. Residence T-101 has averaged a yearly gross rental income of approximately $90,000 over the past three years, making it a compelling opportunity for investors, seasonal owners, or those seeking a flexible coastal retreat with established returns. Positioned directly on the sand, this rare walk-out Gulf-front residence features a private patio just steps from the turquoise waters of the Gulf of Mexico—ideal for enjoying sunset views over the shoreline. The professionally designed interior blends coastal comfort with modern updates, featuring imported contemporary porcelain flooring from Italy throughout the open layout. The kitchen offers updated cabinetry, stone countertops, white appliances, and a seamless connection to the living and dining areas—perfect for relaxed beachside living or hosting guests. Impact windows with plantation shutters and impact glass sliders enhance peace of mind while filling the space with natural light. The spacious bedroom accommodates guests comfortably, while the completely updated bathroom (2021) showcases clean, timeless finishes. Step outside to the travertine-tiled Gulf-front patio, your private vantage point overlooking the beach, dunes, and horizon—an amenity highly valued by renters and owners alike. Turtle Crawl Inn is known for its laid-back resort atmosphere and strong rental appeal, offering a heated swimming pool, beachside cabanas, gas grilling stations, picnic areas, fishing opportunities, a putting green, shuffleboard courts, and deeded beach access. Flexible rental options make this community especially attractive for income-focused ownership. ** The Seller requests NO SOLICITATION COMMUNICATIONS of any kind. LISTING WITHDRAWN, WILL BE RE-ACTIVATED.** Located on the desirable mid-island stretch of Longboat Key, the property is minutes from waterfront dining, marinas, Bayfront Park, Joan M. Durante Park, and boating access. Anna Maria Island lies just to the north, while St. Armands Circle and downtown Sarasota’s shopping, dining, and cultural attractions are a short drive south. Whether you’re seeking a high-performing income property, a personal beachfront escape, or a blend of both, this Gulf-front residence delivers proven rental history, prime location, and direct beach access—a rare combination on Longboat Key. 1 Beds ⋅ 1 Baths ⋅ Turtle Crawl SubDv. ⋅ 34228 Zip Code Turnkey furnished and direct Gulf-front, this exceptional ground-floor residence at Turtle Crawl Inn on Longboat Key offers both effortless beachfront living and remarkable, documented rental performance. Residence T-101 has averaged a yearly gross rental income of approximately $90,000 over the past three years, making it a compelling opportunity for investors, seasonal owners, or those seeking a flexible coastal retreat with established returns. Positioned directly on the sand, this rare walk-out Gulf-front residence features a private patio just steps from the turquoise waters of the Gulf of Mexico—ideal for enjoying sunset views over the shoreline. The professionally designed interior blends coastal comfort with modern updates, featuring imported contemporary porcelain flooring from Italy throughout the open layout. The kitchen offers updated cabinetry, stone countertops, white appliances, and a seamless connection to the living and dining areas—perfect for relaxed beachside living or hosting guests. Impact windows with plantation shutters and impact glass sliders enhance peace of mind while filling the space with natural light. The spacious bedroom accommodates guests comfortably, while the completely updated bathroom (2021) showcases clean, timeless finishes. Step outside to the travertine-tiled Gulf-front patio, your private vantage point overlooking the beach, dunes, and horizon—an amenity highly valued by renters and owners alike. Turtle Crawl Inn is known for its laid-back resort atmosphere and strong rental appeal, offering a heated swimming pool, beachside cabanas, gas grilling stations, picnic areas, fishing opportunities, a putting green, shuffleboard courts, and deeded beach access. Flexible rental options make this community especially attractive for income-focused ownership. ** The Seller requests NO SOLICITATION COMMUNICATIONS of any kind. LISTING WITHDRAWN, WILL BE RE-ACTIVATED.** Located on the desirable mid-island stretch of Longboat Key, the property is minutes from waterfront dining, marinas, Bayfront Park, Joan M. Durante Park, and boating access. Anna Maria Island lies just to the north, while St. Armands Circle and downtown Sarasota’s shopping, dining, and cultural attractions are a short drive south. Whether you’re seeking a high-performing income property, a personal beachfront escape, or a blend of both, this Gulf-front residence delivers proven rental history, prime location, and direct beach access—a rare combination on Longboat Key. 4235 Gulf Of Mexico Drive Unit T101, Longboat Key
$770,000 Virtually Staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors open to a private balcony with breathtaking ocean views. Both bedrooms feature spacious walk-in closets, ceiling fans, while both bathrooms have been fully remodeled with modern, high-end finishes and Toto washlet toilets. The newly updated kitchen boasts a sleek induction stove with a vented range hood, perfect for cooking with a view. New AC, LED lighting, and brand-new impact sliding doors enhance comfort and efficiency. Beyond your private oasis, take advantage of resort-style amenities, including two Gulf-front heated pools unique to the Westchester, Elevators, tennis courts, and direct beach access. Plus, you’re conveniently located just minutes from Publix, top-rated restaurants, and boutique shopping. Enjoy short rides to the vibrant St. Armands Circle and downtown Sarasota, where world-class dining, entertainment, and cultural attractions await. This is coastal luxury at its finest—don’t miss your chance to own a piece of paradise! 2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code Virtually Staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors open to a private balcony with breathtaking ocean views. Both bedrooms feature spacious walk-in closets, ceiling fans, while both bathrooms have been fully remodeled with modern, high-end finishes and Toto washlet toilets. The newly updated kitchen boasts a sleek induction stove with a vented range hood, perfect for cooking with a view. New AC, LED lighting, and brand-new impact sliding doors enhance comfort and efficiency. Beyond your private oasis, take advantage of resort-style amenities, including two Gulf-front heated pools unique to the Westchester, Elevators, tennis courts, and direct beach access. Plus, you’re conveniently located just minutes from Publix, top-rated restaurants, and boutique shopping. Enjoy short rides to the vibrant St. Armands Circle and downtown Sarasota, where world-class dining, entertainment, and cultural attractions await. This is coastal luxury at its finest—don’t miss your chance to own a piece of paradise! 4835 Gulf Of Mexico Drive Unit 302B, Longboat Key
$758,500 Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities. 2 Beds ⋅ 2 Baths ⋅ Winding Oaks SubDv. ⋅ 34228 Zip Code Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities. 3466 Winding Oaks Drive Unit 35, Longboat Key
$750,000 An incredible opportunity to purchase a canal front home on a 10,000 sf lot with 100 feet on the waterfront! Priced for you to bring your vision and remodel or tear it down and build your dream island getaway on the fabulous North end of Longboat Key. A short walk or bike ride to the neighborhood beach access and with no high rises on this end of the island, some days it feels like its privately yours! The home is on a nicely elevated lot and suffered only minimal water intrusion in the storms from 2 years ago. As new multi million dollar homes are going up everywhere, don't miss your chance to get this one at lot value! 2 Beds ⋅ 2 Baths ⋅ Sleepy Lagoon Park SubDv. ⋅ 34228 Zip Code An incredible opportunity to purchase a canal front home on a 10,000 sf lot with 100 feet on the waterfront! Priced for you to bring your vision and remodel or tear it down and build your dream island getaway on the fabulous North end of Longboat Key. A short walk or bike ride to the neighborhood beach access and with no high rises on this end of the island, some days it feels like its privately yours! The home is on a nicely elevated lot and suffered only minimal water intrusion in the storms from 2 years ago. As new multi million dollar homes are going up everywhere, don't miss your chance to get this one at lot value! 535 De Narvaez Drive, Longboat Key
$750,000 Welcome to a true hidden gem of tropical paradise at Bayport Beach and Tennis Club on Longboat Key. Designed by renowned architect Tim Seibert, this one-of-a-kind community spans 27 lush, tropical acres and offers an unmatched coastal lifestyle with 1,200 feet of pristine private beach, where chairs and umbrellas are ready for you to enjoy endless days along the Gulf. As you arrive, you’re immediately surrounded by beautifully maintained grounds and the relaxed, resort-style atmosphere that makes this community so special. Stepping inside this spacious 2 bedroom, 2 bathroom furnished residence, you’re welcomed by a light and airy interior with terracotta-look tile flooring flowing throughout the main living areas, setting a warm coastal tone. The kitchen has been thoughtfully renovated with all new cabinetry, under-cabinet lighting, quartz countertops, a modern backsplash, and stainless steel appliances, creating a clean and functional space that opens seamlessly into the living and dining areas. The expansive living room is both inviting and impressive, designed to feel like a single-family home, with stunning Sarasota Bay views that instantly capture your attention. Shutter doors provide privacy while leading into a sunroom, offering a flexible space to relax and take in the scenery. The owner’s suite is a true retreat, complete with a dedicated office nook perfectly positioned to enjoy peaceful water views. The ensuite bathroom features dual quartz-topped vanities and a walk-in closet, combining comfort and convenience. A split bedroom floorplan ensures privacy, with the guest bedroom offering its own walk-in closet and easy access to the updated guest bathroom. An in-unit laundry area adds to the everyday ease of living. Step outside onto your expansive private deck, where breathtaking views of Sarasota Bay create the perfect backdrop for morning coffee, evening wine, or entertaining guests while surrounded by nature. Bayport Beach and Tennis Club offers an incredible array of amenities, including a Junior-Olympic heated pool, four Har-Tru tennis courts, a fitness center, fishing pier, kayak storage + launch, and an active clubhouse filled with social events. Scenic walking trails wind through the property, where you’ll often spot local wildlife such as osprey, herons, ibis, and egrets, enhancing the serene, natural setting. Just moments away, Bayfront Park offers pickleball courts, green space, and stunning bay views, while St. Armands Circle provides exceptional shopping and dining. A short drive over the iconic Ringling Bridge brings you into vibrant downtown Sarasota, known for its world-class arts scene, including theaters, museums, galleries, and waterfront dining. From private beach access to unmatched amenities and breathtaking bay views, this residence offers the perfect blend of comfort, nature, and coastal elegance in one of Longboat Key’s most sought-after communities. 2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code Welcome to a true hidden gem of tropical paradise at Bayport Beach and Tennis Club on Longboat Key. Designed by renowned architect Tim Seibert, this one-of-a-kind community spans 27 lush, tropical acres and offers an unmatched coastal lifestyle with 1,200 feet of pristine private beach, where chairs and umbrellas are ready for you to enjoy endless days along the Gulf. As you arrive, you’re immediately surrounded by beautifully maintained grounds and the relaxed, resort-style atmosphere that makes this community so special. Stepping inside this spacious 2 bedroom, 2 bathroom furnished residence, you’re welcomed by a light and airy interior with terracotta-look tile flooring flowing throughout the main living areas, setting a warm coastal tone. The kitchen has been thoughtfully renovated with all new cabinetry, under-cabinet lighting, quartz countertops, a modern backsplash, and stainless steel appliances, creating a clean and functional space that opens seamlessly into the living and dining areas. The expansive living room is both inviting and impressive, designed to feel like a single-family home, with stunning Sarasota Bay views that instantly capture your attention. Shutter doors provide privacy while leading into a sunroom, offering a flexible space to relax and take in the scenery. The owner’s suite is a true retreat, complete with a dedicated office nook perfectly positioned to enjoy peaceful water views. The ensuite bathroom features dual quartz-topped vanities and a walk-in closet, combining comfort and convenience. A split bedroom floorplan ensures privacy, with the guest bedroom offering its own walk-in closet and easy access to the updated guest bathroom. An in-unit laundry area adds to the everyday ease of living. Step outside onto your expansive private deck, where breathtaking views of Sarasota Bay create the perfect backdrop for morning coffee, evening wine, or entertaining guests while surrounded by nature. Bayport Beach and Tennis Club offers an incredible array of amenities, including a Junior-Olympic heated pool, four Har-Tru tennis courts, a fitness center, fishing pier, kayak storage + launch, and an active clubhouse filled with social events. Scenic walking trails wind through the property, where you’ll often spot local wildlife such as osprey, herons, ibis, and egrets, enhancing the serene, natural setting. Just moments away, Bayfront Park offers pickleball courts, green space, and stunning bay views, while St. Armands Circle provides exceptional shopping and dining. A short drive over the iconic Ringling Bridge brings you into vibrant downtown Sarasota, known for its world-class arts scene, including theaters, museums, galleries, and waterfront dining. From private beach access to unmatched amenities and breathtaking bay views, this residence offers the perfect blend of comfort, nature, and coastal elegance in one of Longboat Key’s most sought-after communities. 815 Bayport Way Unit 815, Longboat Key
$750,000 One or more photo(s) has been virtually staged. A NEW PRICE!! Wake up to tranquil canal views and end your day with sunsets just steps from the Gulf — all on Longboat Key! Priced UNDER $1M & Renovation Loan Eligible! Opportunities like this are rare, and this property is priced to sell fast. Featuring 2 bedrooms, 2 bathrooms, and a 1-car garage, this home also includes a separate 1-bedroom, 1-bathroom GARAGE APARTMENT with its own entrance—perfect for SHORT TERM RENTALS or guest accommodations. Sitting directly on a CANAL with room to dock a boat, this home is a dream for boaters and beach lovers alike. The 120 feet of reinforced seawall ensures lasting waterfront stability. Enjoy DEEDED BEACH ACCESS, just a short stroll away, where you can witness the magic of turtle nesting season. Walk to dog-friendly Durante Park, the scenic shores of Sarasota Bay, and some of Longboat Key’s most popular restaurants, including Lo’Key and Harry’s Continental Kitchen. Cannon’s Marina is nearby for all your boating needs, and the trolley provides easy access to Anna Maria Island. The home boasts a 2024 AC and a 5-year-old tile roof, giving you peace of mind on major updates. The private outdoor space is perfect for soaking up Florida’s year-round sunshine. Renovation Loan Eligible – Plus an Incredible Build Opportunity! This property qualifies for a renovation loan, allowing you to finance both the purchase and renovations—an incredible opportunity to customize your dream home while keeping costs manageable. Waterfront. Deeded beach access. Room for a boat. Rental potential. And all for UNDER $1 MILLION! This is an **unbeatable opportunity** in one of the most desirable locations on the Gulf Coast. Don’t miss out—schedule your showing today! 2 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code One or more photo(s) has been virtually staged. A NEW PRICE!! Wake up to tranquil canal views and end your day with sunsets just steps from the Gulf — all on Longboat Key! Priced UNDER $1M & Renovation Loan Eligible! Opportunities like this are rare, and this property is priced to sell fast. Featuring 2 bedrooms, 2 bathrooms, and a 1-car garage, this home also includes a separate 1-bedroom, 1-bathroom GARAGE APARTMENT with its own entrance—perfect for SHORT TERM RENTALS or guest accommodations. Sitting directly on a CANAL with room to dock a boat, this home is a dream for boaters and beach lovers alike. The 120 feet of reinforced seawall ensures lasting waterfront stability. Enjoy DEEDED BEACH ACCESS, just a short stroll away, where you can witness the magic of turtle nesting season. Walk to dog-friendly Durante Park, the scenic shores of Sarasota Bay, and some of Longboat Key’s most popular restaurants, including Lo’Key and Harry’s Continental Kitchen. Cannon’s Marina is nearby for all your boating needs, and the trolley provides easy access to Anna Maria Island. The home boasts a 2024 AC and a 5-year-old tile roof, giving you peace of mind on major updates. The private outdoor space is perfect for soaking up Florida’s year-round sunshine. Renovation Loan Eligible – Plus an Incredible Build Opportunity! This property qualifies for a renovation loan, allowing you to finance both the purchase and renovations—an incredible opportunity to customize your dream home while keeping costs manageable. Waterfront. Deeded beach access. Room for a boat. Rental potential. And all for UNDER $1 MILLION! This is an **unbeatable opportunity** in one of the most desirable locations on the Gulf Coast. Don’t miss out—schedule your showing today! 636 Tarawitt Drive, Longboat Key
$749,000 Experience breathtaking, full Gulf views from this beautifully maintained 5th-floor residence at Seaplace on Longboat Key. This furnished 2-bedroom, 2-bath condominium offers the perfect blend of comfort, space, and coastal charm, with expansive living and dining areas designed to capture stunning water views and natural light throughout. Step out to your private lanai and enjoy panoramic sunsets, gentle sea breezes, and the soothing sounds of the Gulf—your own peaceful retreat just steps from the beach. The spacious primary suite provides a relaxing escape, while the guest bedroom offers comfort and privacy for visitors. Seaplace residents enjoy resort-style amenities across 42 acres of lush, meticulously maintained grounds, including a half-mile of private beachfront, two heated swimming pools with spas, a fitness center, Har-Tru tennis courts, walking paths, outdoor grilling areas, and an active, well-managed association. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this unit is priced to sell and ready for you to start enjoying the Longboat Key lifestyle. Schedule your private showing today! 2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code Experience breathtaking, full Gulf views from this beautifully maintained 5th-floor residence at Seaplace on Longboat Key. This furnished 2-bedroom, 2-bath condominium offers the perfect blend of comfort, space, and coastal charm, with expansive living and dining areas designed to capture stunning water views and natural light throughout. Step out to your private lanai and enjoy panoramic sunsets, gentle sea breezes, and the soothing sounds of the Gulf—your own peaceful retreat just steps from the beach. The spacious primary suite provides a relaxing escape, while the guest bedroom offers comfort and privacy for visitors. Seaplace residents enjoy resort-style amenities across 42 acres of lush, meticulously maintained grounds, including a half-mile of private beachfront, two heated swimming pools with spas, a fitness center, Har-Tru tennis courts, walking paths, outdoor grilling areas, and an active, well-managed association. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this unit is priced to sell and ready for you to start enjoying the Longboat Key lifestyle. Schedule your private showing today! 2045 Gulf Of Mexico Drive Unit M1-511, Longboat Key
$740,000 Owner Financing Available! Nestled in the heart of Longboat Key's coveted historic Longbeach Village, this exceptional island retreat offers 3 bedrooms and 3 bathrooms across two charming Key West-style cottages just moments from both the most pristine Gulf beaches and beautiful Sarasota Bay. This rare property blends timeless coastal elegance with modern updates in a private, landscaped setting. The main residence features a bright, open floor plan and an updated kitchen with quartz countertops, hardwood cabinetry, newer appliances, and abundant natural light. The detached guest cottage offers a private 1-bedroom, 1-bath layout complete with its own kitchen and entrance, providing the perfect space for guests, extended family, or added flexibility. Outdoor living is equally inviting with a spacious entertaining deck, tiki bar, and mature tropical landscaping that creates a true sense of privacy and retreat, with room to add a pool. Recent improvements include a new roof on the main residence (2026), Hardie Board siding, updated cabinetry, quartz countertops, updated appliances throughout, fresh paint, and a newer A/C system, offering peace of mind and modern comfort. With proven rental income, this property serves as an exceptional investment opportunity while maintaining strong personal use potential. Situated in the highly desirable “Village“, one of the most charming, inviting, and community-driven neighborhoods on Longboat Key, residents enjoy a rare blend of coastal character and close-knit island living. Just moments from Whitney Beach, community fishing docks, a boat and kayak launch, and exclusive waterfront dining destinations such as Mar Vista and The Shore, this home captures the essence of luxury island living in one of the island’s most beloved enclaves. Schedule your private showing TODAY before it’s gone !! 3 Beds ⋅ 3 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code Owner Financing Available! Nestled in the heart of Longboat Key's coveted historic Longbeach Village, this exceptional island retreat offers 3 bedrooms and 3 bathrooms across two charming Key West-style cottages just moments from both the most pristine Gulf beaches and beautiful Sarasota Bay. This rare property blends timeless coastal elegance with modern updates in a private, landscaped setting. The main residence features a bright, open floor plan and an updated kitchen with quartz countertops, hardwood cabinetry, newer appliances, and abundant natural light. The detached guest cottage offers a private 1-bedroom, 1-bath layout complete with its own kitchen and entrance, providing the perfect space for guests, extended family, or added flexibility. Outdoor living is equally inviting with a spacious entertaining deck, tiki bar, and mature tropical landscaping that creates a true sense of privacy and retreat, with room to add a pool. Recent improvements include a new roof on the main residence (2026), Hardie Board siding, updated cabinetry, quartz countertops, updated appliances throughout, fresh paint, and a newer A/C system, offering peace of mind and modern comfort. With proven rental income, this property serves as an exceptional investment opportunity while maintaining strong personal use potential. Situated in the highly desirable “Village“, one of the most charming, inviting, and community-driven neighborhoods on Longboat Key, residents enjoy a rare blend of coastal character and close-knit island living. Just moments from Whitney Beach, community fishing docks, a boat and kayak launch, and exclusive waterfront dining destinations such as Mar Vista and The Shore, this home captures the essence of luxury island living in one of the island’s most beloved enclaves. Schedule your private showing TODAY before it’s gone !! 660 Linley Street, Longboat Key
$740,000 Situated behind gates of the coveted Bay Isles on Longboat Key is the private enclave of Harbour Oaks. This meticulously renovated second floor residence offers an effortless blend of comfort, refinement, and coastal living. Offering an expansive 3 bedrooms, 2 bathrooms as well as a 2-car garage overlooking one of the most pristine Longboat Key Club golf courses. Furniture conveys with a few personal exceptions. Vaulted ceilings as well as skylights allow natural light to flood through the entire space. The custom modern kitchen is well-appointed with KitchenAid appliances including a 36-inch induction cooktop, built-in oven, refrigerator and dishwasher as well as a dedicated wine refrigerator within the expansive kitchen island. The master bedroom offers vaulted ceilings with a connected terrace to enjoy your morning coffee or watch beautiful Gulf sunsets. The primary bath exudes a sense of being at a spa with its tiled shower, glass shower door and double sink vanity. The third bedroom is currently being used as an office and gym, however could easily be set up as a bedroom. Harbour Oaks is also pet friendly and close to shopping, golf, tennis, beach and bay. Walks and bike rides can be enjoyed in one of the most scenic areas on Longboat Key. Bay Isles offers an exceptional coastal lifestyle including two fully staffed, 24-hour security entrances and exclusive access to a private, gated Gulf-front beach club. Residents have access to a thoughtfully appointed beachside retreat featuring a shaded pavilion, picnic spaces, restrooms, dedicated beach chair storage, grilling stations, and generous parking. Within minutes, access the famous St Armand’s Circle with its exceptional shopping and dining amenities. Cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining. Additional amenities are available within Bay Isles upon joining the Longboat Key Club. 3 Beds ⋅ 2 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code Situated behind gates of the coveted Bay Isles on Longboat Key is the private enclave of Harbour Oaks. This meticulously renovated second floor residence offers an effortless blend of comfort, refinement, and coastal living. Offering an expansive 3 bedrooms, 2 bathrooms as well as a 2-car garage overlooking one of the most pristine Longboat Key Club golf courses. Furniture conveys with a few personal exceptions. Vaulted ceilings as well as skylights allow natural light to flood through the entire space. The custom modern kitchen is well-appointed with KitchenAid appliances including a 36-inch induction cooktop, built-in oven, refrigerator and dishwasher as well as a dedicated wine refrigerator within the expansive kitchen island. The master bedroom offers vaulted ceilings with a connected terrace to enjoy your morning coffee or watch beautiful Gulf sunsets. The primary bath exudes a sense of being at a spa with its tiled shower, glass shower door and double sink vanity. The third bedroom is currently being used as an office and gym, however could easily be set up as a bedroom. Harbour Oaks is also pet friendly and close to shopping, golf, tennis, beach and bay. Walks and bike rides can be enjoyed in one of the most scenic areas on Longboat Key. Bay Isles offers an exceptional coastal lifestyle including two fully staffed, 24-hour security entrances and exclusive access to a private, gated Gulf-front beach club. Residents have access to a thoughtfully appointed beachside retreat featuring a shaded pavilion, picnic spaces, restrooms, dedicated beach chair storage, grilling stations, and generous parking. Within minutes, access the famous St Armand’s Circle with its exceptional shopping and dining amenities. Cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining. Additional amenities are available within Bay Isles upon joining the Longboat Key Club. 2155 Harbourside Drive Unit 804, Longboat Key
$740,000 PRICED TO SELL! Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks community on Longboat Key. This one-story, 3-bedroom, 2.5-bath residence spans 2,219 sq. ft. and offers a host of desirable features—including a private pool, 2-car garage, and deeded beach access through the exclusive Bay Isles Beach Club. A new roof (2025) and fresh interior paint ensure peace of mind and a move-in-ready experience. High ceilings fill the home with natural light, enhancing the spacious feel throughout. The expansive living room, anchored by a wood-burning fireplace, seamlessly connects to the outdoor living area via pocket sliding glass doors, opening to two large screened lanais—ideal for both relaxing and entertaining. The chef’s kitchen is outfitted with granite countertops, stainless steel appliances, rich wood cabinetry, a breakfast bar, and a skylight for added brightness. The primary suite is a private retreat featuring a walk-in closet, two additional closets, updated master bath, and sliding doors leading to the terrace. A guest suite with en suite bath provides comfort and privacy for visitors. Additional highlights include an interior laundry room with sink, a newer AC unit (2018), and natural gas line for adding a pool heater. All furnishings are included. Residents of Harbour Oaks enjoy a resort-style lifestyle with access to a community pool, spa, and lushly landscaped surroundings—just minutes from Longboat Key’s vibrant Town Center. As part of Bay Isles, you’ll have exclusive access to the Bay Isles Beach Club, a private, gated Gulf-front oasis with a pavilion, picnic areas, BBQ grills, beach chairs, restrooms, and ample parking—perfect for sunset viewing or relaxing on Longboat Key’s pristine white sands. Optional membership opportunities at the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deep-water slips offer even more ways to elevate your coastal lifestyle. 3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code PRICED TO SELL! Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks community on Longboat Key. This one-story, 3-bedroom, 2.5-bath residence spans 2,219 sq. ft. and offers a host of desirable features—including a private pool, 2-car garage, and deeded beach access through the exclusive Bay Isles Beach Club. A new roof (2025) and fresh interior paint ensure peace of mind and a move-in-ready experience. High ceilings fill the home with natural light, enhancing the spacious feel throughout. The expansive living room, anchored by a wood-burning fireplace, seamlessly connects to the outdoor living area via pocket sliding glass doors, opening to two large screened lanais—ideal for both relaxing and entertaining. The chef’s kitchen is outfitted with granite countertops, stainless steel appliances, rich wood cabinetry, a breakfast bar, and a skylight for added brightness. The primary suite is a private retreat featuring a walk-in closet, two additional closets, updated master bath, and sliding doors leading to the terrace. A guest suite with en suite bath provides comfort and privacy for visitors. Additional highlights include an interior laundry room with sink, a newer AC unit (2018), and natural gas line for adding a pool heater. All furnishings are included. Residents of Harbour Oaks enjoy a resort-style lifestyle with access to a community pool, spa, and lushly landscaped surroundings—just minutes from Longboat Key’s vibrant Town Center. As part of Bay Isles, you’ll have exclusive access to the Bay Isles Beach Club, a private, gated Gulf-front oasis with a pavilion, picnic areas, BBQ grills, beach chairs, restrooms, and ample parking—perfect for sunset viewing or relaxing on Longboat Key’s pristine white sands. Optional membership opportunities at the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deep-water slips offer even more ways to elevate your coastal lifestyle. 2181 Harbourside Drive Unit 1403, Longboat Key
$737,000 Penthouse-Level Condo at Grand Bay – Longboat Key Experience luxury living in this beautifully appointed penthouse-level residence at Grand Bay, located behind the gates of Bay Isles on Longboat Key. This spacious 2-bedroom, 2-bath condo offers an open and airy floor plan with stunning east-to-west exposure, capturing both sunrise and sunset from dual balconies with sweeping views of Sarasota Bay, the city skyline, and the golf course. As a penthouse-level home, it also features an added ceiling height of one foot, enhancing the sense of space and light throughout. Both bedrooms are en-suite, with the primary suite featuring dual closets (including one walk-in) and luxurious marble vanities in the bath. The home showcases elegant bamboo flooring in the main living area, marble tile in the bathrooms, and plush carpet in the bedrooms. Floor-to-ceiling sliding glass doors at both ends of the unit flood the space with natural light. The chef’s kitchen is equipped with a Sub-Zero refrigerator, Blue Pearl granite countertops, a breakfast bar, and an in-kitchen laundry room. Recent upgrades include a new AC system in 2021 and a water heater in 2020. The residence also comes with two deeded parking spaces and a private garage-level storage locker, and it is offered furnished for immediate enjoyment. Grand Bay’s exceptional amenities include 24-hour guard-gated Bay Isles entry, an additional Grand Bay gated entrance, secure coded lobby access, on-site property management, and a pet-friendly environment. Residents enjoy two resort-style pools, a state-of-the-art fitness center, tennis courts, and membership to the Bay Isles Beach Club. There are no current or pending assessments. Enjoy the perfect blend of luxury, privacy, and convenience in one of Longboat Key’s premier waterfront communities. 2 Beds ⋅ 2 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code Penthouse-Level Condo at Grand Bay – Longboat Key Experience luxury living in this beautifully appointed penthouse-level residence at Grand Bay, located behind the gates of Bay Isles on Longboat Key. This spacious 2-bedroom, 2-bath condo offers an open and airy floor plan with stunning east-to-west exposure, capturing both sunrise and sunset from dual balconies with sweeping views of Sarasota Bay, the city skyline, and the golf course. As a penthouse-level home, it also features an added ceiling height of one foot, enhancing the sense of space and light throughout. Both bedrooms are en-suite, with the primary suite featuring dual closets (including one walk-in) and luxurious marble vanities in the bath. The home showcases elegant bamboo flooring in the main living area, marble tile in the bathrooms, and plush carpet in the bedrooms. Floor-to-ceiling sliding glass doors at both ends of the unit flood the space with natural light. The chef’s kitchen is equipped with a Sub-Zero refrigerator, Blue Pearl granite countertops, a breakfast bar, and an in-kitchen laundry room. Recent upgrades include a new AC system in 2021 and a water heater in 2020. The residence also comes with two deeded parking spaces and a private garage-level storage locker, and it is offered furnished for immediate enjoyment. Grand Bay’s exceptional amenities include 24-hour guard-gated Bay Isles entry, an additional Grand Bay gated entrance, secure coded lobby access, on-site property management, and a pet-friendly environment. Residents enjoy two resort-style pools, a state-of-the-art fitness center, tennis courts, and membership to the Bay Isles Beach Club. There are no current or pending assessments. Enjoy the perfect blend of luxury, privacy, and convenience in one of Longboat Key’s premier waterfront communities. 3070 Grand Bay Boulevard Unit 644, Longboat Key
$735,000 Under contract. Accepting back up offers. Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the residence includes a large walkout screened lanai where you can enjoy gentle Gulf breezes and spectacular sunsets over the tranquil waters of the Gulf of Mexico. The thoughtfully designed layout provides abundant storage throughout, including generous closets in both bedrooms as well as a dedicated owner’s closet. Just steps from the unit, the pristine beach is a renowned nesting ground for sea turtles, offering the unique opportunity to watch dolphins and manatees pass by while relaxing on one of Florida’s most beautiful beaches. Cedars West residents enjoy a wide range of resort-style amenities, including a large heated and cooled swimming pool, two tennis courts, BBQ grilling areas, and convenient kayak and bike racks. Owners also have the option to generate rental income by taking advantage of Cedars West’s rare two-week minimum rental policy on Longboat Key. Don’t miss this incredible opportunity to experience the ultimate beachfront lifestyle. 2 Beds ⋅ 2 Baths ⋅ Cedars West Of Longboat Inc SubDv. ⋅ 34228 Zip Code Under contract. Accepting back up offers. Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the residence includes a large walkout screened lanai where you can enjoy gentle Gulf breezes and spectacular sunsets over the tranquil waters of the Gulf of Mexico. The thoughtfully designed layout provides abundant storage throughout, including generous closets in both bedrooms as well as a dedicated owner’s closet. Just steps from the unit, the pristine beach is a renowned nesting ground for sea turtles, offering the unique opportunity to watch dolphins and manatees pass by while relaxing on one of Florida’s most beautiful beaches. Cedars West residents enjoy a wide range of resort-style amenities, including a large heated and cooled swimming pool, two tennis courts, BBQ grilling areas, and convenient kayak and bike racks. Owners also have the option to generate rental income by taking advantage of Cedars West’s rare two-week minimum rental policy on Longboat Key. Don’t miss this incredible opportunity to experience the ultimate beachfront lifestyle. 5655 Gulf Of Mexico Drive Unit D107, Longboat Key
$725,000 Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips. 3 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips. 2110 Harbourside Drive Unit 536, Longboat Key
$725,000 A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, restaurant, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet. Bay Isles SubDv. ⋅ 34228 Zip Code A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, restaurant, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet. 2800 Harbourside Drive Drive Unit D-19 D-20, Longboat Key
$724,000 Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately. 2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately. 2020 Harbourside Drive Unit 457, Longboat Key
$720,000 BEACHFRONT CONDO with FANTASTIC BEACH & GULF VIEW. Enjoy coastal living at its best in this beautifully updated 2-bedroom, 2-bath condo with 1,257 sq ft under air, located on the fourth floor of the highly sought-after Seaplace Community on Longboat Key. This residence offers fantastic Gulf and beach views, higher ceiling height than many units, and a screened lanai where you can relax with refreshing sea breezes and sparkling water views. Inside, you’ll find newer appliances, kitchen backsplash, wood flooring throughout the kitchen, living room, second bedroom, and second bathroom, a newer water heater, Murphy bed, folding doors in the second bedroom, updated ceiling trim in the living room, and fresh interior paint completed about a year ago. Seaplace is a gated, resort-style beachfront community known for its lush landscaping and outstanding amenities, including direct beach access, two heated pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, a one-mile walking trail, and a remodeled clubhouse with fitness center, sauna, library, and Gulf-view patio with BBQ grills, along with 24-hour guard-gated security and on-site management. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this condo is perfect as a vacation home, investment property, or full-time residence, offering an exceptional blend of comfort, convenience, and beachfront lifestyle. 2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code BEACHFRONT CONDO with FANTASTIC BEACH & GULF VIEW. Enjoy coastal living at its best in this beautifully updated 2-bedroom, 2-bath condo with 1,257 sq ft under air, located on the fourth floor of the highly sought-after Seaplace Community on Longboat Key. This residence offers fantastic Gulf and beach views, higher ceiling height than many units, and a screened lanai where you can relax with refreshing sea breezes and sparkling water views. Inside, you’ll find newer appliances, kitchen backsplash, wood flooring throughout the kitchen, living room, second bedroom, and second bathroom, a newer water heater, Murphy bed, folding doors in the second bedroom, updated ceiling trim in the living room, and fresh interior paint completed about a year ago. Seaplace is a gated, resort-style beachfront community known for its lush landscaping and outstanding amenities, including direct beach access, two heated pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, a one-mile walking trail, and a remodeled clubhouse with fitness center, sauna, library, and Gulf-view patio with BBQ grills, along with 24-hour guard-gated security and on-site management. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this condo is perfect as a vacation home, investment property, or full-time residence, offering an exceptional blend of comfort, convenience, and beachfront lifestyle. 1965 Gulf Of Mexico Drive Unit G5-407, Longboat Key
$700,000 This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect blend of classy with a modern flair. Before entering the home take note of the huge 16’ x 13’ outdoor deck where you can enjoy a partial view of the Gulf. It's a great place to start your day with a cup of morning coffee, or enjoy a nice meal in the evening, and catch the spectacular colors of the sky as the sun sets! Step inside to this inviting, beautifully appointed 2-bedroom 2-bath condominium with luxury vinyl flooring and crown molding throughout. The entire living/ dining areas, lanai, both bedrooms and second bathroom have all been recently updated. Giving the condo a fresh polished appearance accentuated by recessed glass display shelving and an abundance of recessed lights. The depth of workmanship in the updates carries onto the stylized door moldings into the primary bedroom. All popcorn has been removed! The kitchen offers a coffee bar, stainless steel appliances, a pantry, a nice arrangement of cabinets, and granite countertops open to the dining room and living room, perfect for entertaining. Take in the view of the lush tropical landscape and gorgeous pond right below the lanai that is open to the living room. Perfect for a Murphy bed, extra living space, a reading nook or your second favorite spot for your morning coffee as the sun rises. The primary bedroom offers an additional 6’ by 6’ area that is perfect for an office desk looking out over nature. The primary also offers a walk-in closet and a generously sized ensuite bath with dual vanities. Bayport Beach & Tennis Club is a gem with 27 tropical landscaped acres and 1200 feet of private Gulf waterfront deeded access. Where you can grab a chair and umbrella and soak up the sun, or take in the breathtaking sunsets. Enjoy Sarasota Bay just outside your door and stroll to the private dock where you can fish, kayak, paddleboard, and watch for the manatees and dolphins as they cruise by. This community also offers a clubhouse, fitness center, 4 Har-Ter tennis courts, golf practice net, and a Junior-Olympic heated pool. Bayport Beach & Tennis Club consists of 17 buildings built between 1979 and 1983. Designed by architect Tim Seibert of the Sarasota School of Architecture. Located mid-key with a wealth of attractions moments away, including Bayfront Park, steps away, offering Pickle Ball, Basketball, Shuffleboard courts, playground, bike paths, kayak launch and Publix 2 miles away. 2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect blend of classy with a modern flair. Before entering the home take note of the huge 16’ x 13’ outdoor deck where you can enjoy a partial view of the Gulf. It's a great place to start your day with a cup of morning coffee, or enjoy a nice meal in the evening, and catch the spectacular colors of the sky as the sun sets! Step inside to this inviting, beautifully appointed 2-bedroom 2-bath condominium with luxury vinyl flooring and crown molding throughout. The entire living/ dining areas, lanai, both bedrooms and second bathroom have all been recently updated. Giving the condo a fresh polished appearance accentuated by recessed glass display shelving and an abundance of recessed lights. The depth of workmanship in the updates carries onto the stylized door moldings into the primary bedroom. All popcorn has been removed! The kitchen offers a coffee bar, stainless steel appliances, a pantry, a nice arrangement of cabinets, and granite countertops open to the dining room and living room, perfect for entertaining. Take in the view of the lush tropical landscape and gorgeous pond right below the lanai that is open to the living room. Perfect for a Murphy bed, extra living space, a reading nook or your second favorite spot for your morning coffee as the sun rises. The primary bedroom offers an additional 6’ by 6’ area that is perfect for an office desk looking out over nature. The primary also offers a walk-in closet and a generously sized ensuite bath with dual vanities. Bayport Beach & Tennis Club is a gem with 27 tropical landscaped acres and 1200 feet of private Gulf waterfront deeded access. Where you can grab a chair and umbrella and soak up the sun, or take in the breathtaking sunsets. Enjoy Sarasota Bay just outside your door and stroll to the private dock where you can fish, kayak, paddleboard, and watch for the manatees and dolphins as they cruise by. This community also offers a clubhouse, fitness center, 4 Har-Ter tennis courts, golf practice net, and a Junior-Olympic heated pool. Bayport Beach & Tennis Club consists of 17 buildings built between 1979 and 1983. Designed by architect Tim Seibert of the Sarasota School of Architecture. Located mid-key with a wealth of attractions moments away, including Bayfront Park, steps away, offering Pickle Ball, Basketball, Shuffleboard courts, playground, bike paths, kayak launch and Publix 2 miles away. 706 Bayport Way Unit 706, Longboat Key
$700,000 Virtually Staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces highlight scenic views and offer the option of installing a gas grill. Inside, soaring two-story ceilings define the main living area, creating an airy, light-filled atmosphere enhanced by expansive windows that frame picturesque views of the lagoon, resort-style pool w/ waterfall features, tropical plantings and the waters of Sarasota Bay and distant city skyline. The open living and dining spaces are ideal for both relaxed everyday living and entertaining, anchored by a fireplace and generous wall space for art. From the entry patio, unexpected Bay and city views provide a striking first impression and a unique urban-meets-coastal backdrop. The residence features three full bedrooms and three and a half baths. The upper-level retreat with its full bath has a terrace with elevated views across the natural preserve toward the city. This home presents a true blank canvas, thoughtfully priced to allow the new owner to reimagine and transform it into their own vision of refined coastal living. A deeded, private two-car garage adds exceptional convenience and value—an uncommon and highly desirable feature. Located on the coveted south end of Longboat Key, Tangerine Bay Club is a gated, pet-friendly community close to Lido Beach, dining and boutique shopping on St. Armands Circle, and the cultural, dining, and arts scene of downtown Sarasota. Optional Bay Isles Beach Club membership is available, providing exclusive access to a private, gated four-acre Gulf of Mexico beach facility, reserved for a select group of members—ideal for beach gatherings, sunset celebrations, and effortless days by the sea. An outstanding opportunity to embrace the Florida lifestyle in one of Longboat Key’s most desirable bayfront communities. 3 Beds ⋅ 4 Baths ⋅ Tangerine Bay Club SubDv. ⋅ 34228 Zip Code Virtually Staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces highlight scenic views and offer the option of installing a gas grill. Inside, soaring two-story ceilings define the main living area, creating an airy, light-filled atmosphere enhanced by expansive windows that frame picturesque views of the lagoon, resort-style pool w/ waterfall features, tropical plantings and the waters of Sarasota Bay and distant city skyline. The open living and dining spaces are ideal for both relaxed everyday living and entertaining, anchored by a fireplace and generous wall space for art. From the entry patio, unexpected Bay and city views provide a striking first impression and a unique urban-meets-coastal backdrop. The residence features three full bedrooms and three and a half baths. The upper-level retreat with its full bath has a terrace with elevated views across the natural preserve toward the city. This home presents a true blank canvas, thoughtfully priced to allow the new owner to reimagine and transform it into their own vision of refined coastal living. A deeded, private two-car garage adds exceptional convenience and value—an uncommon and highly desirable feature. Located on the coveted south end of Longboat Key, Tangerine Bay Club is a gated, pet-friendly community close to Lido Beach, dining and boutique shopping on St. Armands Circle, and the cultural, dining, and arts scene of downtown Sarasota. Optional Bay Isles Beach Club membership is available, providing exclusive access to a private, gated four-acre Gulf of Mexico beach facility, reserved for a select group of members—ideal for beach gatherings, sunset celebrations, and effortless days by the sea. An outstanding opportunity to embrace the Florida lifestyle in one of Longboat Key’s most desirable bayfront communities. 350 Gulf Of Mexico Drive Unit 234, Longboat Key
$700,000 Investment Opportunity with low HOA fees! Beautifully updated and decorated two-bedroom, two-bath unit with vaulted ceilings can sleep up to 6 at Casa Del Mar on Longboat Key. Casa Del Mar is a popular beach resort with short-term rentals located directly on the Gulf. Use the condo for your own vacation and enjoy all Longboat Key has to offer while collecting income the rest of the year. This turnkey furnished condo is tiled throughout and offers views of the tropically landscaped courtyard and partial Gulf views from the extended living area. The primary ensuite bedroom is furnished with a king size bed and built-in cabinetry. The guest bedroom is furnished with 2 twin beds, built-in cabinetry with a full bath in the hallway. The kitchen has stone counters, solid wood cabinets and stainless appliances. Community amenities include a huge 30’ x 60’ gulf front heated pool, grill area, tennis, pickleball and basketball. Complimentary beach lounges are provided for guests and umbrella rentals are available. Casa Del Mar’s on-site management handles year-round bookings along with all the details so you can enjoy your investment stress-free. Annual gross income for #14F: 2023 $45,131, 2024 $59,833, and 2025 $56,388. Great location convenient to St Armand’s Circle with shops, fine and casual dining, and entertainment and a short drive over the bridge to the southwest cultural hub of downtown Sarasota. 2 Beds ⋅ 2 Baths ⋅ Casa Del Mar SubDv. ⋅ 34228 Zip Code Investment Opportunity with low HOA fees! Beautifully updated and decorated two-bedroom, two-bath unit with vaulted ceilings can sleep up to 6 at Casa Del Mar on Longboat Key. Casa Del Mar is a popular beach resort with short-term rentals located directly on the Gulf. Use the condo for your own vacation and enjoy all Longboat Key has to offer while collecting income the rest of the year. This turnkey furnished condo is tiled throughout and offers views of the tropically landscaped courtyard and partial Gulf views from the extended living area. The primary ensuite bedroom is furnished with a king size bed and built-in cabinetry. The guest bedroom is furnished with 2 twin beds, built-in cabinetry with a full bath in the hallway. The kitchen has stone counters, solid wood cabinets and stainless appliances. Community amenities include a huge 30’ x 60’ gulf front heated pool, grill area, tennis, pickleball and basketball. Complimentary beach lounges are provided for guests and umbrella rentals are available. Casa Del Mar’s on-site management handles year-round bookings along with all the details so you can enjoy your investment stress-free. Annual gross income for #14F: 2023 $45,131, 2024 $59,833, and 2025 $56,388. Great location convenient to St Armand’s Circle with shops, fine and casual dining, and entertainment and a short drive over the bridge to the southwest cultural hub of downtown Sarasota. 4621 Gulf Of Mexico Drive Unit 14F, Longboat Key
$695,000 Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The centerpiece of the kitchen is the large, strategically custom-designed quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42-inch cabinetry, stainless steel appliances, large undermount sink with a push-button garbage disposal, lovely backsplash and lots of storage with an abundance of additional counter space, ideally designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized, classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9-by-6-foot in villa laundry room with new Electrolux washer and dryer. All hurricane-grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay, with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center, which makes this a useful space. Go outside onto the brick paver patio and lounge, grill and relax with the sound and views of Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, air conditioner in 2020 and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community, which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico, with restaurants you can get to by boat. The Spanish Main maintenance-free community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for affordable leasing. Beach access is ideal for those numerous beach days and magnificent sunsets. This pet-friendly very active 55-plus community are added benefits for your enjoyment. Only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events Sarasota and St. Armands Circle have to offer. Private second-deeded parking place with this villa. 2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The centerpiece of the kitchen is the large, strategically custom-designed quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42-inch cabinetry, stainless steel appliances, large undermount sink with a push-button garbage disposal, lovely backsplash and lots of storage with an abundance of additional counter space, ideally designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized, classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9-by-6-foot in villa laundry room with new Electrolux washer and dryer. All hurricane-grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay, with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center, which makes this a useful space. Go outside onto the brick paver patio and lounge, grill and relax with the sound and views of Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, air conditioner in 2020 and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community, which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico, with restaurants you can get to by boat. The Spanish Main maintenance-free community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for affordable leasing. Beach access is ideal for those numerous beach days and magnificent sunsets. This pet-friendly very active 55-plus community are added benefits for your enjoyment. Only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events Sarasota and St. Armands Circle have to offer. Private second-deeded parking place with this villa. 925 Spanish Drive N, Longboat Key
$687,000 Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full. 2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full. 4825 Gulf Of Mexico Drive Unit 105, Longboat Key
$685,000 GORGEOUS BAYFRONT PENTHOUSE VIEWS--RARE TOP FLOOR OPPORTUNITY!! Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. 2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code GORGEOUS BAYFRONT PENTHOUSE VIEWS--RARE TOP FLOOR OPPORTUNITY!! Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. 4500 Gulf Of Mexico Drive Unit 3, Longboat Key
$677,500 Enjoy peaceful lagoon views from this completely remodeled Junior Suite. Sold turnkey furnished and currently in the hotel program, the Junior Suites in this building have 10’ ceilings unlike the other buildings. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace. As an owner in the hotel program you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, spa, fitness center, white sand beach with umbrellas & waitstaff, and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying your Longboat Life today! 1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code Enjoy peaceful lagoon views from this completely remodeled Junior Suite. Sold turnkey furnished and currently in the hotel program, the Junior Suites in this building have 10’ ceilings unlike the other buildings. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace. As an owner in the hotel program you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, spa, fitness center, white sand beach with umbrellas & waitstaff, and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying your Longboat Life today! 225 Sands Point Road Unit 7101, Longboat Key
$675,000 NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open seamlessly to two screened lanais, and a generously sized guest suite accommodating two double beds. A private laundry room with full-size washer and dryer, two interior storage closets, and a spacious exterior storage unit add exceptional convenience. Offered furnished with select exclusions. Milestone inspections are complete and assessments paid in full—delivering confidence and long-term value. Westchester is an exclusive, impeccably managed beachfront community set on 7 acres with 700 feet of shoreline, featuring two heated pools, beach loungers, tiki huts, pickleball and tennis courts, shuffleboard, BBQ grills, kayak and bicycle storage, and on-site management. A new clubhouse with a fitness center and enhanced Gulf-side pool and landscaping are underway. A rare opportunity for elevated coastal living and investment excellence. CHECK THE VIRTUAL TOUR, and reserve your private viewing 2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open seamlessly to two screened lanais, and a generously sized guest suite accommodating two double beds. A private laundry room with full-size washer and dryer, two interior storage closets, and a spacious exterior storage unit add exceptional convenience. Offered furnished with select exclusions. Milestone inspections are complete and assessments paid in full—delivering confidence and long-term value. Westchester is an exclusive, impeccably managed beachfront community set on 7 acres with 700 feet of shoreline, featuring two heated pools, beach loungers, tiki huts, pickleball and tennis courts, shuffleboard, BBQ grills, kayak and bicycle storage, and on-site management. A new clubhouse with a fitness center and enhanced Gulf-side pool and landscaping are underway. A rare opportunity for elevated coastal living and investment excellence. CHECK THE VIRTUAL TOUR, and reserve your private viewing 4805 Gulf Of Mexico Drive Unit 103, Longboat Key
$675,000 An exceptional opportunity to own a private family retreat on the pristine shores of Longboat Key—while generating rental income when you’re away. Located within the intimate beachfront enclave of Sea Grape Inn, this unique resort community offers just eight residences, creating a peaceful, uncrowded atmosphere rarely found on the island. Approved for daily, weekly, or monthly rentals, the property provides excellent flexibility for both personal enjoyment and investment potential. From the moment you arrive, the difference is clear. Each residence is thoughtfully appointed and lives more like a private coastal home than a typical vacation rental. This beautifully maintained condo features stone countertops, updated cabinetry, abundant appliances, and tile flooring throughout. The screened porch serves as a tranquil retreat—perfect for enjoying gentle Gulf breezes, spectacular sunsets, and lush tropical landscaping. Step outside to enjoy the heated beachfront pool overlooking the Gulf—an ideal setting for relaxing swims while taking in sweeping water views. The uncrowded beach is just beyond, with chairs provided for effortless seaside enjoyment. Additional amenities include on-site laundry, a BBQ gazebo area, beach towels, and internet service—everything needed for a seamless coastal getaway. Professional on-site management handles all rentals, marketing, cleaning, bookkeeping, and administrative details, offering truly turnkey ownership with no hidden charges. The residence is being offered turnkey furnished, ready for immediate enjoyment or continued rental success. Ideally situated near local restaurants, nature trails, parks with tennis and pickleball, and convenient shopping, this property combines privacy with accessibility. Financials are available upon request. The condo enjoys strong rental demand; showings will be accommodated with 24-hour notice and guest approval. Please contact the listing agent for availability. Life truly is better on Longboat Key! 2 Beds ⋅ 2 Baths ⋅ Seagrape Inn Condo SubDv. ⋅ 34228 Zip Code An exceptional opportunity to own a private family retreat on the pristine shores of Longboat Key—while generating rental income when you’re away. Located within the intimate beachfront enclave of Sea Grape Inn, this unique resort community offers just eight residences, creating a peaceful, uncrowded atmosphere rarely found on the island. Approved for daily, weekly, or monthly rentals, the property provides excellent flexibility for both personal enjoyment and investment potential. From the moment you arrive, the difference is clear. Each residence is thoughtfully appointed and lives more like a private coastal home than a typical vacation rental. This beautifully maintained condo features stone countertops, updated cabinetry, abundant appliances, and tile flooring throughout. The screened porch serves as a tranquil retreat—perfect for enjoying gentle Gulf breezes, spectacular sunsets, and lush tropical landscaping. Step outside to enjoy the heated beachfront pool overlooking the Gulf—an ideal setting for relaxing swims while taking in sweeping water views. The uncrowded beach is just beyond, with chairs provided for effortless seaside enjoyment. Additional amenities include on-site laundry, a BBQ gazebo area, beach towels, and internet service—everything needed for a seamless coastal getaway. Professional on-site management handles all rentals, marketing, cleaning, bookkeeping, and administrative details, offering truly turnkey ownership with no hidden charges. The residence is being offered turnkey furnished, ready for immediate enjoyment or continued rental success. Ideally situated near local restaurants, nature trails, parks with tennis and pickleball, and convenient shopping, this property combines privacy with accessibility. Financials are available upon request. The condo enjoys strong rental demand; showings will be accommodated with 24-hour notice and guest approval. Please contact the listing agent for availability. Life truly is better on Longboat Key! 5125 Gulf Of Mexico Drive Unit 4, Longboat Key
$671,500 A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours! 2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours! 4900 Gulf Of Mexico Drive Unit 203, Longboat Key