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$22,000,000

Named the House of Columns by world-renowned, award-winning architect Carl Abbott, this palatial Bayfront estate stands as a singular expression of architectural distinction and craftsmanship. Encompassing close to five acres on the north end of Longboat Key spanning Sarasota Bay, the combined offering of 6610 and 6630 Gulf of Mexico Drive represents one of the most significant residential holdings available in the area, a legacy estate where endless views of sea and sky create an unforgettable backdrop for living. The property unfolds like a private peninsula, offering exceptional width, depth and privacy. On the eastern shoreline, calm bay waters reflect the morning light with open water, protected shoreline and bridgeless access to the Gulf of Mexico. The primary residence is gracefully positioned on the bayfront, designed to capture eastern exposure and long, tranquil water views across Sarasota Bay. Clean architectural lines, soaring interior volumes, and walls of glass create a continuous dialogue between interior and exterior. Ceilings soar up to 21 feet, allowing light to move freely throughout the home while maintaining warmth and livability. The elevator provides access across levels, while Lutron lighting and automated shades on every window and door allow the home to respond intuitively to the changing light of day. The residence has been impeccably maintained by its original owner, reflecting a level of care and stewardship rarely found. Infrastructure has been thoughtfully addressed, including a whole-home generator that ensures continuity and peace of mind. The owner’s garage sits under a cantilever with access to the interior elevator and an additional air-conditioned four-car garage with large workspace offers a total space for 6 cars and exceptional flexibility for collectors, hobbies or future customization. A lagoon-style pool sits within the landscape, offering a resort-like atmosphere while preserving privacy and water views. A private dock with two boat lifts provides immediate access to Sarasota Bay and the Intracoastal Waterway, creating a seamless boating lifestyle that complements the estate’s waterfrontage. The inclusion of 6630 Gulf of Mexico Drive allows owners to construct a guest house or secondary structure, offering flexibility for multigenerational living, guests, or staff accommodations, offering extraordinary future optionality and ensures the next owner retains control over one of Longboat Key’s irreplaceable resources, land. What ultimately distinguishes this offering is its irreplaceability. Estates of this size, with this combination of architectural pedigree, boating infrastructure, development flexibility and maintained condition are no longer being created. Despite its scale and seclusion, you are moments from the refined lifestyle Longboat Key is known for, private clubs, championship golf, fine dining, IMG Academy and the cultural offerings of Anna Maria Island, St. Armands Circle and downtown Sarasota just beyond the bridge. This is not merely a waterfront home, it is a generational legacy, unmatched in design, scale, privacy and location.

4 Beds ⋅ 7 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Named the House of Columns by world-renowned, award-winning architect Carl Abbott, this palatial Bayfront estate stands as a singular expression of architectural distinction and craftsmanship. Encompassing close to five acres on the north end of Longboat Key spanning Sarasota Bay, the combined offering of 6610 and 6630 Gulf of Mexico Drive represents one of the most significant residential holdings available in the area, a legacy estate where endless views of sea and sky create an unforgettable backdrop for living. The property unfolds like a private peninsula, offering exceptional width, depth and privacy. On the eastern shoreline, calm bay waters reflect the morning light with open water, protected shoreline and bridgeless access to the Gulf of Mexico. The primary residence is gracefully positioned on the bayfront, designed to capture eastern exposure and long, tranquil water views across Sarasota Bay. Clean architectural lines, soaring interior volumes, and walls of glass create a continuous dialogue between interior and exterior. Ceilings soar up to 21 feet, allowing light to move freely throughout the home while maintaining warmth and livability. The elevator provides access across levels, while Lutron lighting and automated shades on every window and door allow the home to respond intuitively to the changing light of day. The residence has been impeccably maintained by its original owner, reflecting a level of care and stewardship rarely found. Infrastructure has been thoughtfully addressed, including a whole-home generator that ensures continuity and peace of mind. The owner’s garage sits under a cantilever with access to the interior elevator and an additional air-conditioned four-car garage with large workspace offers a total space for 6 cars and exceptional flexibility for collectors, hobbies or future customization. A lagoon-style pool sits within the landscape, offering a resort-like atmosphere while preserving privacy and water views. A private dock with two boat lifts provides immediate access to Sarasota Bay and the Intracoastal Waterway, creating a seamless boating lifestyle that complements the estate’s waterfrontage. The inclusion of 6630 Gulf of Mexico Drive allows owners to construct a guest house or secondary structure, offering flexibility for multigenerational living, guests, or staff accommodations, offering extraordinary future optionality and ensures the next owner retains control over one of Longboat Key’s irreplaceable resources, land. What ultimately distinguishes this offering is its irreplaceability. Estates of this size, with this combination of architectural pedigree, boating infrastructure, development flexibility and maintained condition are no longer being created. Despite its scale and seclusion, you are moments from the refined lifestyle Longboat Key is known for, private clubs, championship golf, fine dining, IMG Academy and the cultural offerings of Anna Maria Island, St. Armands Circle and downtown Sarasota just beyond the bridge. This is not merely a waterfront home, it is a generational legacy, unmatched in design, scale, privacy and location.

6610 Gulf Of Mexico Drive, Longboat Key

$2,100,000

The Sanctuary behind the gates of the Longboat Key Club located on the beachfront is one of the most desirable addresses on Longboat Key, Florida. New to the market, this full on, direct Gulf view residence B305 in Building III at 545 Sanctuary Drive offers about 3,000 square feet with three bedrooms & 2 ½ bathrooms providing spacious and elegant beach front living. From the handsome double door entry, the gleaming marble floor dining area invites you into this luxurious condominium home. Then, you will be treated to a sparkling like diamonds daytime Gulf water views or in the evening, breathtaking sunsets in shades of purple & orange. These magnificent direct Gulf views can be enjoyed from the attractively furnished living room and the serene primary bedroom & of course from the 21-foot-long covered Gulf side terrace. This unique Carlyle floorplan also features a second, east facing private terrace which can be accessed through the guest bedroom as well as from the handsome kitchen as you enjoy morning sunrises with a cup of coffee. This beach retreat is in impeccable condition with high quality furnishings plus electric storm shutters on all sliding doors. This unit also has one under building garage space #150 plus a climate controlled storage cage. Decorated in neutral tones, this home offers coastal elegant style throughout. The cozy eat in kitchen has custom built light wood cabinetry, high end finishes, cream colored granite counter tops, tile backsplash & double ovens. The gracious, large primary bedroom suite is a tranquil retreat with Gulf water views, a large walk-in closet & a spa like En Suite bathroom with double sinks, a soaking tub & a walk-in shower. The Sanctuary offers an exclusive resort lifestyle. The beautiful beach front measures 1200 feet of pristine white sand. The resort style, heated Olympic sized swimming pool includes a 25 meter lap lane plus there is a separate outdoor whirlpool & fire pit area. Amenities include two lighted Har-Tru tennis courts & a state of the art fitness center with saunas located in the newly redecorated clubhouse which offers a fully equipped kitchen & entertainment room. On site management, 24 hour security & 18 acres of meticulously maintained grounds & beach enhance the sense of exclusivity & security.

3 Beds ⋅ 3 Baths ⋅ Sanctuary Iii SubDv. ⋅ 34228 Zip Code

The Sanctuary behind the gates of the Longboat Key Club located on the beachfront is one of the most desirable addresses on Longboat Key, Florida. New to the market, this full on, direct Gulf view residence B305 in Building III at 545 Sanctuary Drive offers about 3,000 square feet with three bedrooms & 2 ½ bathrooms providing spacious and elegant beach front living. From the handsome double door entry, the gleaming marble floor dining area invites you into this luxurious condominium home. Then, you will be treated to a sparkling like diamonds daytime Gulf water views or in the evening, breathtaking sunsets in shades of purple & orange. These magnificent direct Gulf views can be enjoyed from the attractively furnished living room and the serene primary bedroom & of course from the 21-foot-long covered Gulf side terrace. This unique Carlyle floorplan also features a second, east facing private terrace which can be accessed through the guest bedroom as well as from the handsome kitchen as you enjoy morning sunrises with a cup of coffee. This beach retreat is in impeccable condition with high quality furnishings plus electric storm shutters on all sliding doors. This unit also has one under building garage space #150 plus a climate controlled storage cage. Decorated in neutral tones, this home offers coastal elegant style throughout. The cozy eat in kitchen has custom built light wood cabinetry, high end finishes, cream colored granite counter tops, tile backsplash & double ovens. The gracious, large primary bedroom suite is a tranquil retreat with Gulf water views, a large walk-in closet & a spa like En Suite bathroom with double sinks, a soaking tub & a walk-in shower. The Sanctuary offers an exclusive resort lifestyle. The beautiful beach front measures 1200 feet of pristine white sand. The resort style, heated Olympic sized swimming pool includes a 25 meter lap lane plus there is a separate outdoor whirlpool & fire pit area. Amenities include two lighted Har-Tru tennis courts & a state of the art fitness center with saunas located in the newly redecorated clubhouse which offers a fully equipped kitchen & entertainment room. On site management, 24 hour security & 18 acres of meticulously maintained grounds & beach enhance the sense of exclusivity & security.

545 Sanctuary Drive Unit B305, Longboat Key

$2,100,000

$100,000 PRICE REDUCTION—NOW OFFERED AT $2,100,000! Exceptional Longboat Key waterfront living just THREE HOMES FROM SARASOTA BAY. This completely renovated 3-bedroom, 2-bath canal-front home offers 1,853 sq. ft. of air-conditioned living space and 2,461 total sq. ft., combining an outstanding boating location with extensive recent improvements. Boaters will appreciate the newer seawall, 16,000-lb boat lift and 18' x 16' Trex dock with lighting and water, offering views toward Sarasota Bay and quick access to open water. Enjoy your private Pebble Tec pool and paver pool deck, both updated in 2024. Major improvements include a NEW FLAT TILE ROOF (2025), Carrier A/C (2024), A.O. Smith water heater, NuCORE waterproof flooring and plantation shutters throughout. The updated kitchen features Silestone quartz countertops, stainless-steel sink, Bosch 3-door refrigerator/freezer and dishwasher, plus stainless-steel GE range and microwave. The spacious living room features vaulted ceilings and recessed lighting, complemented by a separate dining room. The primary suite offers a walk-in closet with built-ins and an ensuite bath with dual sinks, large tiled shower, whirlpool tub and private water closet. A split-bedroom floor plan provides privacy for guests, with walk-in closets and an office area incorporated into the third bedroom. With major renovations completed, a private pool, exceptional boating amenities and a premier location just three homes from Sarasota Bay, 548 Gunwale Lane offers an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle. NOW OFFERED AT $2,100,000!

3 Beds ⋅ 2 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

$100,000 PRICE REDUCTION—NOW OFFERED AT $2,100,000! Exceptional Longboat Key waterfront living just THREE HOMES FROM SARASOTA BAY. This completely renovated 3-bedroom, 2-bath canal-front home offers 1,853 sq. ft. of air-conditioned living space and 2,461 total sq. ft., combining an outstanding boating location with extensive recent improvements. Boaters will appreciate the newer seawall, 16,000-lb boat lift and 18' x 16' Trex dock with lighting and water, offering views toward Sarasota Bay and quick access to open water. Enjoy your private Pebble Tec pool and paver pool deck, both updated in 2024. Major improvements include a NEW FLAT TILE ROOF (2025), Carrier A/C (2024), A.O. Smith water heater, NuCORE waterproof flooring and plantation shutters throughout. The updated kitchen features Silestone quartz countertops, stainless-steel sink, Bosch 3-door refrigerator/freezer and dishwasher, plus stainless-steel GE range and microwave. The spacious living room features vaulted ceilings and recessed lighting, complemented by a separate dining room. The primary suite offers a walk-in closet with built-ins and an ensuite bath with dual sinks, large tiled shower, whirlpool tub and private water closet. A split-bedroom floor plan provides privacy for guests, with walk-in closets and an office area incorporated into the third bedroom. With major renovations completed, a private pool, exceptional boating amenities and a premier location just three homes from Sarasota Bay, 548 Gunwale Lane offers an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle. NOW OFFERED AT $2,100,000!

548 Gunwale Lane, Longboat Key

$3,750,000

Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *NOW UNFURNISHED*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, approximately 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.

3 Beds ⋅ 3 Baths ⋅ Sanctuary SubDv. ⋅ 34228 Zip Code

Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *NOW UNFURNISHED*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, approximately 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.

535 Sanctuary Drive Unit C807, Longboat Key

$899,900

Four Diamond Resort with five restaurants, 45 holes of Golf, Spa, Marina, 21 Tennis courts on Longboat Key!!!. This income producing property on the beachside with a golf course view is calling you!!!. It's a one-bedroom studio at the Resort on Longboat Key, a gated community. Presently the unit is in the Resort rental program and the owner may use the unit 28 days per year.

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

Four Diamond Resort with five restaurants, 45 holes of Golf, Spa, Marina, 21 Tennis courts on Longboat Key!!!. This income producing property on the beachside with a golf course view is calling you!!!. It's a one-bedroom studio at the Resort on Longboat Key, a gated community. Presently the unit is in the Resort rental program and the owner may use the unit 28 days per year.

250 Sands Point Road Unit 5203, Longboat Key

$2,999,000

Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.

4 Beds ⋅ 4 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.

1005 Bogey Lane, Longboat Key

$550,000

Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code

Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.

4420 Exeter Drive Unit 303, Longboat Key

$1,395,000

Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.

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

Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.

1485 Gulf Of Mexico Drive Unit 303, Longboat Key

$1,420,000

NEW PRICE, AMAZING OPPORTUNITY!!! Experience the ultimate island lifestyle in this masterfully renovated 2,880 sqft, 4 Bed/3 Bath "lock-and-leave" condo at Cedars Tennis Resort and Club. Elevated sanctuary on the tranquil north end of Longboat Key. Offering the expansive feel of a single-family residence with the effortless "lock-and-leave" ease of being in the beautiful condo community of Cedars Tennis Resort and Club. This exquisite 4BR/3BA retreat defines coastal chic. A private elevator serves all three levels, opening into a sun-drenched great room with soaring ceilings, a fireplace, and a gourmet kitchen featuring dual islands and designer finishes. The refined dining room opens right off of this space with its custom built-in cabinetry and dry bar, ideal for any social gathering. Relax on your private, screened lanais overlooking lush tropical foliage and serene ponds, with peek-a-boo views of the Gulf. There is one on each living level. Rounding out the main living area is a versatile den/office (currently used as the 4th bedroom), a full third bathroom, beautiful hardwood floors throughout and a dedicated laundry room. The primary suite is a true oasis with a spa-inspired sunken bath, large walk-in shower, dual vanities and walk-in closets. Upstairs beyond the oasis of a primary there are two additional oversized guest bedrooms and a beautifully renovated guest bathroom with a walk-in shower. Recent updates beyond the full interior renovation include 2026 garage door replacements, and 2024 roof and AC replacement. Hardi- Board siding on exterior and Pella high-impact windows. The split 3-car garage provides total peace of mind and the rare abundance of space and storage. Nestled in the 66-acre village-like townhome community enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Cedars East is the rare community on LBK that offers shorter-term rental allowance with its 2-week minimum, making it the perfect balance for offsetting costs when not in use, without living in a hotel community. Exceptional onsite management is in place if desired. Fantastic residence, rare opportunity, come take a look today!

4 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

NEW PRICE, AMAZING OPPORTUNITY!!! Experience the ultimate island lifestyle in this masterfully renovated 2,880 sqft, 4 Bed/3 Bath "lock-and-leave" condo at Cedars Tennis Resort and Club. Elevated sanctuary on the tranquil north end of Longboat Key. Offering the expansive feel of a single-family residence with the effortless "lock-and-leave" ease of being in the beautiful condo community of Cedars Tennis Resort and Club. This exquisite 4BR/3BA retreat defines coastal chic. A private elevator serves all three levels, opening into a sun-drenched great room with soaring ceilings, a fireplace, and a gourmet kitchen featuring dual islands and designer finishes. The refined dining room opens right off of this space with its custom built-in cabinetry and dry bar, ideal for any social gathering. Relax on your private, screened lanais overlooking lush tropical foliage and serene ponds, with peek-a-boo views of the Gulf. There is one on each living level. Rounding out the main living area is a versatile den/office (currently used as the 4th bedroom), a full third bathroom, beautiful hardwood floors throughout and a dedicated laundry room. The primary suite is a true oasis with a spa-inspired sunken bath, large walk-in shower, dual vanities and walk-in closets. Upstairs beyond the oasis of a primary there are two additional oversized guest bedrooms and a beautifully renovated guest bathroom with a walk-in shower. Recent updates beyond the full interior renovation include 2026 garage door replacements, and 2024 roof and AC replacement. Hardi- Board siding on exterior and Pella high-impact windows. The split 3-car garage provides total peace of mind and the rare abundance of space and storage. Nestled in the 66-acre village-like townhome community enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Cedars East is the rare community on LBK that offers shorter-term rental allowance with its 2-week minimum, making it the perfect balance for offsetting costs when not in use, without living in a hotel community. Exceptional onsite management is in place if desired. Fantastic residence, rare opportunity, come take a look today!

515 Forest Way, Longboat Key

$4,550,000

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.

4 Beds ⋅ 4 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.

1571 Harbor Cay Lane, Longboat Key

$1,460,000

Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!

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

Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!

3040 Grand Bay Boulevard Unit 213, Longboat Key

$13,995,000

This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

4 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code

This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

6489 Gulfside Road, Longboat Key

$499,000

Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

1 Beds ⋅ 1 Baths ⋅ Covert Condominium SubDv. ⋅ 34228 Zip Code

Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

5231 Gulf Of Mexico Drive Unit 104, Longboat Key

$3,499,900

Virtually Staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern rear exposure overlooking the canal, with a north-facing street frontage, providing balanced natural light throughout the day. The home underwent a comprehensive renovation in 2018, including a tile roof, paver driveway, two Trane A/C units, tankless water heater, updated sprinkler system, railings, pool equipment, and a Pebble Tec refinished pool positioned to maximize the southern exposure. The interior features an open great-room layout with 16-foot ceilings, porcelain tile flooring throughout, plantation shutters, LED lighting, and a spacious kitchen with Starmark solid-wood soft-close cabinetry, Cambria quartz countertops, and stainless-steel appliances. An 8-foot arched iron front door introduces abundant natural light and an open, functional floor plan. The current configuration includes an upper-level primary suite with solid oak flooring, walk-in closets, and a well-appointed bath, while the first level offers three large bedrooms, including an office with custom built-ins, and two full baths with handcrafted cabinetry, quartz countertops, and glass-enclosed showers. The flexible layout provides the opportunity to create a first-floor primary suite to suit individual lifestyle needs. Boating amenities include a new seawall, a 70-foot private Trex dock with 50-amp shore power, and a recently serviced 10,000-pound boat lift. Outdoor living is enhanced by a covered lanai and a two-level travertine deck ideal for entertaining and enjoying the canal setting. Residents enjoy access to a private deeded beach on the Gulf of Mexico and proximity to Longboat Key Club golf, dining, and shopping at St. Armands Circle, with downtown Sarasota’s cultural arts and dining scene just minutes away. Schedule a private showing to experience this waterfront home, its flexible living options, and direct access to Sarasota Bay

4 Beds ⋅ 3 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code

Virtually Staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern rear exposure overlooking the canal, with a north-facing street frontage, providing balanced natural light throughout the day. The home underwent a comprehensive renovation in 2018, including a tile roof, paver driveway, two Trane A/C units, tankless water heater, updated sprinkler system, railings, pool equipment, and a Pebble Tec refinished pool positioned to maximize the southern exposure. The interior features an open great-room layout with 16-foot ceilings, porcelain tile flooring throughout, plantation shutters, LED lighting, and a spacious kitchen with Starmark solid-wood soft-close cabinetry, Cambria quartz countertops, and stainless-steel appliances. An 8-foot arched iron front door introduces abundant natural light and an open, functional floor plan. The current configuration includes an upper-level primary suite with solid oak flooring, walk-in closets, and a well-appointed bath, while the first level offers three large bedrooms, including an office with custom built-ins, and two full baths with handcrafted cabinetry, quartz countertops, and glass-enclosed showers. The flexible layout provides the opportunity to create a first-floor primary suite to suit individual lifestyle needs. Boating amenities include a new seawall, a 70-foot private Trex dock with 50-amp shore power, and a recently serviced 10,000-pound boat lift. Outdoor living is enhanced by a covered lanai and a two-level travertine deck ideal for entertaining and enjoying the canal setting. Residents enjoy access to a private deeded beach on the Gulf of Mexico and proximity to Longboat Key Club golf, dining, and shopping at St. Armands Circle, with downtown Sarasota’s cultural arts and dining scene just minutes away. Schedule a private showing to experience this waterfront home, its flexible living options, and direct access to Sarasota Bay

562 Ranger Lane, Longboat Key

$649,999

This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

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

This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

5260 Gulf Of Mexico Drive Unit 403, Longboat Key

$1,798,000

PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

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

PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

3060 Grand Bay Boulevard Unit 174, Longboat Key

$649,900

Stunning Sarasota Bay Views from a Move-In-Ready First-Floor Spacious Corner Unit! Wake up to breathtaking, unobstructed Sarasota Bay vistas in this turnkey first-floor corner residence, designed with upscale Tommy Bahama–inspired flair. This exceptional home blends luxury island living with immediate rental potential, offering panoramic water views from both the primary and guest bedrooms, while the pool lies just steps from your private patio. Elegantly remodeled, the home showcases porcelain tile floors, solid doors, crown molding, granite windowsills, and solar film on rear windows and sliders for added privacy and comfort. The open, light-filled kitchen is a chef’s delight, featuring solid wood cabinetry, granite countertops, stainless steel appliances, and a double oven range. Both bathrooms are thoughtfully updated with cast-iron tubs, granite countertops, and dedicated heat and air vents. Additional highlights include a full-size in-unit washer and dryer, a large water heater, and covered parking space #67 . The residence comes with a long-standing seasonal tenant and a transferable lease. Located in the premier M Building at Longboat Harbour, residents enjoy resort-style amenities including a private gated beach club(4415 Gulf Of Mexico dr ), four heated pools, tennis and pickleball courts, fitness center, kayak storage, and boat docks on first come base- power and sail boats. A new roof is underway with assessment already paid, and no storm damage has occurred. This is a rare opportunity to own a move-in-ready, elegantly upgraded waterfront retreat in one of Sarasota’s most sought-after communities.

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code

Stunning Sarasota Bay Views from a Move-In-Ready First-Floor Spacious Corner Unit! Wake up to breathtaking, unobstructed Sarasota Bay vistas in this turnkey first-floor corner residence, designed with upscale Tommy Bahama–inspired flair. This exceptional home blends luxury island living with immediate rental potential, offering panoramic water views from both the primary and guest bedrooms, while the pool lies just steps from your private patio. Elegantly remodeled, the home showcases porcelain tile floors, solid doors, crown molding, granite windowsills, and solar film on rear windows and sliders for added privacy and comfort. The open, light-filled kitchen is a chef’s delight, featuring solid wood cabinetry, granite countertops, stainless steel appliances, and a double oven range. Both bathrooms are thoughtfully updated with cast-iron tubs, granite countertops, and dedicated heat and air vents. Additional highlights include a full-size in-unit washer and dryer, a large water heater, and covered parking space #67 . The residence comes with a long-standing seasonal tenant and a transferable lease. Located in the premier M Building at Longboat Harbour, residents enjoy resort-style amenities including a private gated beach club(4415 Gulf Of Mexico dr ), four heated pools, tennis and pickleball courts, fitness center, kayak storage, and boat docks on first come base- power and sail boats. A new roof is underway with assessment already paid, and no storm damage has occurred. This is a rare opportunity to own a move-in-ready, elegantly upgraded waterfront retreat in one of Sarasota’s most sought-after communities.

4430 Exeter Drive Unit M108, Longboat Key

$675,000

Tropical elegance awaits in this thoughtfully updated Junior Suite, which pairs tranquil lagoon views with strong rental potential through the established hotel program. Impact-rated sliding glass doors lead to a private, open terrace with a glass railing, allowing the lush, tropical setting to remain the focal point while inviting the outdoors in. Inside, the residence feels airy and welcoming thanks to 10’ ceilings and a carefully curated blend of textures and finishes. Faux wood tile floors run throughout, complemented by crown molding and warm wall accents with shiplap detailing that add depth and character without overwhelming the space. The dining nook is intimate and inviting, enhanced by a rich wood feature wall that creates a relaxed, comfortable atmosphere for casual meals or evening unwinding. The kitchen is both stylish and efficient, featuring stone countertops, crisp white cabinetry with glass-panel details, stainless steel appliances and a patterned tile backsplash that brings subtle visual interest. The bathroom continues the elevated feel with a spa-inspired design, offering dual vanities, a walk-in glass shower with detailed tilework and natural textures that create a calming retreat after a day in the sun. Offered fully furnished and seamlessly integrated into the hotel rental program, this residence allows owners to enjoy flexibility while benefiting from resort-level operations. Ownership includes access to the exclusive 410-acre Longboat Key Club, with five acclaimed dining venues, 45 holes of championship golf, the award-winning Tennis Gardens, spa and fitness facilities, a private white-sand beach with attendant service, and a full-service marina. Recent property-wide updates to guest rooms, pool areas, dining spaces, and services further enhance the experience at this AAA Four-Diamond destination.

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

Tropical elegance awaits in this thoughtfully updated Junior Suite, which pairs tranquil lagoon views with strong rental potential through the established hotel program. Impact-rated sliding glass doors lead to a private, open terrace with a glass railing, allowing the lush, tropical setting to remain the focal point while inviting the outdoors in. Inside, the residence feels airy and welcoming thanks to 10’ ceilings and a carefully curated blend of textures and finishes. Faux wood tile floors run throughout, complemented by crown molding and warm wall accents with shiplap detailing that add depth and character without overwhelming the space. The dining nook is intimate and inviting, enhanced by a rich wood feature wall that creates a relaxed, comfortable atmosphere for casual meals or evening unwinding. The kitchen is both stylish and efficient, featuring stone countertops, crisp white cabinetry with glass-panel details, stainless steel appliances and a patterned tile backsplash that brings subtle visual interest. The bathroom continues the elevated feel with a spa-inspired design, offering dual vanities, a walk-in glass shower with detailed tilework and natural textures that create a calming retreat after a day in the sun. Offered fully furnished and seamlessly integrated into the hotel rental program, this residence allows owners to enjoy flexibility while benefiting from resort-level operations. Ownership includes access to the exclusive 410-acre Longboat Key Club, with five acclaimed dining venues, 45 holes of championship golf, the award-winning Tennis Gardens, spa and fitness facilities, a private white-sand beach with attendant service, and a full-service marina. Recent property-wide updates to guest rooms, pool areas, dining spaces, and services further enhance the experience at this AAA Four-Diamond destination.

225 Sands Point Road Unit 6201, Longboat Key

$675,000

This beautifully remodeled Junior Suite captures serene lagoon views while offering excellent income potential through the established hotel rental program. Hurricane-impact sliders frame the space and open to a private terrace with glass railing, allowing uninterrupted views across the tropical lagoon setting. Sold fully furnished, this residence is truly turnkey, blending personal enjoyment with resort-style investment appeal. Inside, soaring 10’ ceilings enhance the sense of space and comfort, complemented by faux wood tile floors, crown molding and warm wood accents with shiplap detailing that add texture and character. A quaint dining area features a rich wood accent wall, creating a cozy yet refined atmosphere. The kitchen is thoughtfully appointed with stone countertops, white cabinetry with glass panel accents, stainless steel appliances and a striking tile backsplash that adds visual interest without overpowering the space. The spa-inspired bath continues the elevated feel, finished with shiplap walls, dual vanities and a walk-in glass shower adorned with gorgeous tilework. Every detail has been considered to create a polished, welcoming retreat for guests and owners alike. As part of the hotel program, ownership includes access to the exclusive 410-acre Longboat Key Club. Enjoy 5 distinctive restaurants, 45 holes of championship golf, the renowned Tennis Gardens, spa and fitness facilities, a private white-sand beach with attentive service, and a full-service marina, all proudly recognized with the AAA Four-Diamond Award.

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

This beautifully remodeled Junior Suite captures serene lagoon views while offering excellent income potential through the established hotel rental program. Hurricane-impact sliders frame the space and open to a private terrace with glass railing, allowing uninterrupted views across the tropical lagoon setting. Sold fully furnished, this residence is truly turnkey, blending personal enjoyment with resort-style investment appeal. Inside, soaring 10’ ceilings enhance the sense of space and comfort, complemented by faux wood tile floors, crown molding and warm wood accents with shiplap detailing that add texture and character. A quaint dining area features a rich wood accent wall, creating a cozy yet refined atmosphere. The kitchen is thoughtfully appointed with stone countertops, white cabinetry with glass panel accents, stainless steel appliances and a striking tile backsplash that adds visual interest without overpowering the space. The spa-inspired bath continues the elevated feel, finished with shiplap walls, dual vanities and a walk-in glass shower adorned with gorgeous tilework. Every detail has been considered to create a polished, welcoming retreat for guests and owners alike. As part of the hotel program, ownership includes access to the exclusive 410-acre Longboat Key Club. Enjoy 5 distinctive restaurants, 45 holes of championship golf, the renowned Tennis Gardens, spa and fitness facilities, a private white-sand beach with attentive service, and a full-service marina, all proudly recognized with the AAA Four-Diamond Award.

225 Sands Point Road Unit 7205, Longboat Key

$875,000

Investor Dream Home! A double condo unit which feels like a single-family home and comes with 2 attached oversized garage spaces. Elevated among the treetops on the bay side of Longboat Key, this home features wood floors throughout the first elevated living level, an open great room and kitchen for entertaining. There’s an inviting wood-burning fireplace, screened lanai for bay breezes and a flex room to use as an office, den or guest room. Upstairs you will find 3 bedrooms. Two share a full bath while the primary bedroom features a large ensuite and two walk-in closets. You’ll find stunning views of the bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. Amenities in the premier tennis community include exceptional access to bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!

3 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code

Investor Dream Home! A double condo unit which feels like a single-family home and comes with 2 attached oversized garage spaces. Elevated among the treetops on the bay side of Longboat Key, this home features wood floors throughout the first elevated living level, an open great room and kitchen for entertaining. There’s an inviting wood-burning fireplace, screened lanai for bay breezes and a flex room to use as an office, den or guest room. Upstairs you will find 3 bedrooms. Two share a full bath while the primary bedroom features a large ensuite and two walk-in closets. You’ll find stunning views of the bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. Amenities in the premier tennis community include exceptional access to bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!

836 Evergreen Way, Longboat Key

$2,377,000

Rare Beachfront Opportunity - Two Adjacent Residences at The Islander Club, South Longboat Key Seize a truly rare and unique opportunity to own two adjacent Gulf-front residences in the North Tower of The Islander Club on South Longboat Key. Featuring highly sought-after southwest and northwest exposures, these first-floor walk-out condos live like a maintenance-free beachfront home, with no stairs or elevators and direct access from two private terraces to the Olympic-size beachfront pool and the private white sandy shores of the Gulf of Mexico’s crystal clear aqua waters. Combined, the residences offer 2,500+ square feet of Gulf-front living space, including four beachfront bedrooms and four full bathrooms, two balconies with over 500 square feet of total outdoor frontage, and expansive walls of glass showcasing panoramic Gulf views, brilliant sunshine, gorgeous sunsets, and refreshing cross-breezes. The layout functions as an expansive and seamless beachfront residence with flexible configuration options—combine both units into one refined Gulf-front luxury home, or live in one and rent the other, or tailor and customize the space for personal use or investment potential. Located directly on the beach in South Longboat Key, this one-of-a-kind legacy property is just three miles from St. Armands Circle and minutes from downtown Sarasota’s dining, shopping, and cultural attractions. Two covered parking spaces are included, along with additional guest parking available. The Islander Club features 400 feet of private beachfront, a new fitness and community center, beachfront pool, two Har-Tru tennis courts (soon to be remodeled for pickleball use as well), library, conference room, on-site management, gated access, and a highly advantageous and rare owner-to-owner rental program. Convenient to Publix, CVS, acclaimed restaurants, boutique shopping, and Sarasota’s renowned arts scene. Enjoy breathtaking Gulf sunsets and an unmatched Longboat Key beachfront lifestyle at one of Longboat Key’s most sought-after beachfront addresses.

4 Beds ⋅ 4 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code

Rare Beachfront Opportunity - Two Adjacent Residences at The Islander Club, South Longboat Key Seize a truly rare and unique opportunity to own two adjacent Gulf-front residences in the North Tower of The Islander Club on South Longboat Key. Featuring highly sought-after southwest and northwest exposures, these first-floor walk-out condos live like a maintenance-free beachfront home, with no stairs or elevators and direct access from two private terraces to the Olympic-size beachfront pool and the private white sandy shores of the Gulf of Mexico’s crystal clear aqua waters. Combined, the residences offer 2,500+ square feet of Gulf-front living space, including four beachfront bedrooms and four full bathrooms, two balconies with over 500 square feet of total outdoor frontage, and expansive walls of glass showcasing panoramic Gulf views, brilliant sunshine, gorgeous sunsets, and refreshing cross-breezes. The layout functions as an expansive and seamless beachfront residence with flexible configuration options—combine both units into one refined Gulf-front luxury home, or live in one and rent the other, or tailor and customize the space for personal use or investment potential. Located directly on the beach in South Longboat Key, this one-of-a-kind legacy property is just three miles from St. Armands Circle and minutes from downtown Sarasota’s dining, shopping, and cultural attractions. Two covered parking spaces are included, along with additional guest parking available. The Islander Club features 400 feet of private beachfront, a new fitness and community center, beachfront pool, two Har-Tru tennis courts (soon to be remodeled for pickleball use as well), library, conference room, on-site management, gated access, and a highly advantageous and rare owner-to-owner rental program. Convenient to Publix, CVS, acclaimed restaurants, boutique shopping, and Sarasota’s renowned arts scene. Enjoy breathtaking Gulf sunsets and an unmatched Longboat Key beachfront lifestyle at one of Longboat Key’s most sought-after beachfront addresses.

2301 Gulf Of Mexico Drive Unit 12N and 11N, Longboat Key

$745,000

Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.

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

Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

$7,495,000

Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.

4 Beds ⋅ 5 Baths ⋅ Bonaire Bayou SubDv. ⋅ 34228 Zip Code

Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.

5005 Gulf Of Mexico Drive Unit 4, Longboat Key

$2,750,000

Spectacular North west corner three bedroom condo with direct beachfront views at The Grande, a oasis with only 8 residences. This is Florida living at its very best! This second floor corner location has breathtaking views of the Gulf of Mexico and miles of beautiful sandy beach plus some views of Sarasota Bay and amazing sunsets. A fantastic wrapping terrace on the Gulfside offers outdoor enjoyment from the main living area and master suite. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom, all with private baths, is 3260 square feet. A Gulf front gourmet kitchen with high end appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows that dramatically overlook the Gulf of Mexico and beach, enhance the brightness and open feeling of this home. This home has 10 foot ceilings, and comes with a private enclosed two car garage with direct access.This Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.

3 Beds ⋅ 5 Baths ⋅ Grande At Longboat Key SubDv. ⋅ 34228 Zip Code

Spectacular North west corner three bedroom condo with direct beachfront views at The Grande, a oasis with only 8 residences. This is Florida living at its very best! This second floor corner location has breathtaking views of the Gulf of Mexico and miles of beautiful sandy beach plus some views of Sarasota Bay and amazing sunsets. A fantastic wrapping terrace on the Gulfside offers outdoor enjoyment from the main living area and master suite. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom, all with private baths, is 3260 square feet. A Gulf front gourmet kitchen with high end appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows that dramatically overlook the Gulf of Mexico and beach, enhance the brightness and open feeling of this home. This home has 10 foot ceilings, and comes with a private enclosed two car garage with direct access.This Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.

4561 Gulf Of Mexico Drive Unit 202, Longboat Key

$754,900

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

3 Beds ⋅ 3 Baths ⋅ The Banyan Bay Club SubDv. ⋅ 34228 Zip Code

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

5270 Gulf Of Mexico Drive Unit 508, Longboat Key

$2,325,000

Virtually Staged. Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

4 Beds ⋅ 5 Baths ⋅ Conrad Beach SubDv. ⋅ 34228 Zip Code

Virtually Staged. Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

333 Firehouse Court, Longboat Key

$724,900

Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A well-established vacation rental with a strong income history, this property is an ideal opportunity for both personal enjoyment and investment. Nestled within an intimate beachfront community offering 340 feet of pristine Gulf frontage, Sand Cay provides an exceptional resort-style experience. Residents and guests enjoy first-class amenities including tennis courts, shuffleboard, a heated pool, basketball area, barbecue stations, a full-time on-site manager, and a convenient in-house rental program. Perfectly located, the resort is just minutes from the boutique shops and fine dining of St. Armands Circle and the vibrant arts and cultural attractions of downtown Sarasota. Light and bright, this third-floor garden-view condo is ideally situated between the pool and the beach. The inviting floor plan features two bedrooms, two bathrooms, a spacious living and dining area, an updated and fully equipped kitchen, a cozy den/office nook, and a private balcony with an awning—ideal for morning coffee or unwinding after a day by the Gulf. Your slice of Longboat Key paradise awaits. Schedule your showing today.

2 Beds ⋅ 2 Baths ⋅ Sand Cay A Condominium SubDv. ⋅ 34228 Zip Code

Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A well-established vacation rental with a strong income history, this property is an ideal opportunity for both personal enjoyment and investment. Nestled within an intimate beachfront community offering 340 feet of pristine Gulf frontage, Sand Cay provides an exceptional resort-style experience. Residents and guests enjoy first-class amenities including tennis courts, shuffleboard, a heated pool, basketball area, barbecue stations, a full-time on-site manager, and a convenient in-house rental program. Perfectly located, the resort is just minutes from the boutique shops and fine dining of St. Armands Circle and the vibrant arts and cultural attractions of downtown Sarasota. Light and bright, this third-floor garden-view condo is ideally situated between the pool and the beach. The inviting floor plan features two bedrooms, two bathrooms, a spacious living and dining area, an updated and fully equipped kitchen, a cozy den/office nook, and a private balcony with an awning—ideal for morning coffee or unwinding after a day by the Gulf. Your slice of Longboat Key paradise awaits. Schedule your showing today.

4725 Gulf Of Mexico Drive Unit 314, Longboat Key

$625,000

Huge Price Adjustment! PRICED TO SELL!!! Check out these consistently strong revenue numbers: 2023: $55,764, 2024: $54,307.46, 2025: $62,007.40!!! Whether you choose resort style living or just want to enjoy vacationing at the beach while earning income when you are not using your condo, this is the place for you! The resort is right on the beach and amenities include a large heated pool, several grills, tennis, basketball and pickleball. Repeat guests have commented choosing this unit because of its location and that they love having a screened in patio to enjoy morning coffee or simply the warm gulf air. Casa Del Mar is one of the few resorts in Longboat permitted to offer short term rentals and also offers some of the lowest property management fees as well. Come check out this turnkey 2 bedroom 2 bath condo and make beach living your reality! (approximately 900 sqft with screened in lanai)

2 Beds ⋅ 2 Baths ⋅ Casa Del Mar SubDv. ⋅ 34228 Zip Code

Huge Price Adjustment! PRICED TO SELL!!! Check out these consistently strong revenue numbers: 2023: $55,764, 2024: $54,307.46, 2025: $62,007.40!!! Whether you choose resort style living or just want to enjoy vacationing at the beach while earning income when you are not using your condo, this is the place for you! The resort is right on the beach and amenities include a large heated pool, several grills, tennis, basketball and pickleball. Repeat guests have commented choosing this unit because of its location and that they love having a screened in patio to enjoy morning coffee or simply the warm gulf air. Casa Del Mar is one of the few resorts in Longboat permitted to offer short term rentals and also offers some of the lowest property management fees as well. Come check out this turnkey 2 bedroom 2 bath condo and make beach living your reality! (approximately 900 sqft with screened in lanai)

4621 Gulf Of Mexico Drive Unit 10D, Longboat Key

$640,000

One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $35,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Building E #208 | Corner End Unit • Bay & Harbour Views. CLOSEST BUILDING TO A SHORT WALK ACCROSS THE STREET WITH A PRIVATE DEEDED GULF BEACH ACCESS WITH PAVILION, RESTROOMS AND SHOWERS TOTALLY REMODELED FROM FLOOR TO CEILING second-floor corner residence in the highly sought-after Longboat Harbour Community. This light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour. This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available. From the two bedrooms, you step out to the exceptionally Large Lanai with floor to ceiling sliding glass doors. A SHOWCASE KITCHEN WITH TWO SUNLIT WINDOWS AND WATER VIEWS Elegant, functional, and beautifully appointed: • Frigidaire Professional stainless steel appliances • Gleaming quartz countertops • 9-inch deep sink • Pull-out cabinet shelving • Pantry closet • Designer tile backsplash • Large Eat-In Kitchen with water views & sunsets • Instant hot-water. LUXURIOUS PRIMARY SUITE An elevated retreat professionally designed for comfort and relaxation • Private ensuite bath • Custom California Closet walk-in wardrobe • Built-in desk feature • Remote-controlled luxury solar shades. RESORT-INSPIRED AMENITIES Longboat Harbour offers a lifestyle unmatched on the Gulf Coast: • Designated covered parking spot conveniently located • Personal storage space on the third floor • Private deeded Gulf beach access with pavilion, restrooms & shower • Four sparkling pools • Fitness center & sauna • Tennis & pickleball courts • Billiards room, library & meeting rooms • Picnic areas with grills • Putting green • Fishing pier • Affordable resident-only boat dockage • KAYAK LAUNCH and KAYAK WHICH SELLER WILL BE GIFTING TO THE BUYER. Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key. PROPERTY ENHANCEMENTS & UPDATES: Thoughtfully improved for comfort, reliability, and peace of mind: • NO HURRICANE DAMAGE OR FLOODING • Bosch Washer & Dryer • Newer AC: 12/5/21 • Newer Hot Water Heater: 3/3/17 • New roofs throughout the community • Electrical and plumbing systems updated. A BEAUTIFULLY RENOVATED INTERIOR THAT CREATES THE ULTIMATE COASTAL LIFESTYLE/ THE MONTHLY HOA FEE INCLUDES HAZARD, HURRICANE AND FLOOD INSURANCE/ RESERVES HAVE BEEN FULLY FUNDED

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code

One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $35,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Building E #208 | Corner End Unit • Bay & Harbour Views. CLOSEST BUILDING TO A SHORT WALK ACCROSS THE STREET WITH A PRIVATE DEEDED GULF BEACH ACCESS WITH PAVILION, RESTROOMS AND SHOWERS TOTALLY REMODELED FROM FLOOR TO CEILING second-floor corner residence in the highly sought-after Longboat Harbour Community. This light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour. This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available. From the two bedrooms, you step out to the exceptionally Large Lanai with floor to ceiling sliding glass doors. A SHOWCASE KITCHEN WITH TWO SUNLIT WINDOWS AND WATER VIEWS Elegant, functional, and beautifully appointed: • Frigidaire Professional stainless steel appliances • Gleaming quartz countertops • 9-inch deep sink • Pull-out cabinet shelving • Pantry closet • Designer tile backsplash • Large Eat-In Kitchen with water views & sunsets • Instant hot-water. LUXURIOUS PRIMARY SUITE An elevated retreat professionally designed for comfort and relaxation • Private ensuite bath • Custom California Closet walk-in wardrobe • Built-in desk feature • Remote-controlled luxury solar shades. RESORT-INSPIRED AMENITIES Longboat Harbour offers a lifestyle unmatched on the Gulf Coast: • Designated covered parking spot conveniently located • Personal storage space on the third floor • Private deeded Gulf beach access with pavilion, restrooms & shower • Four sparkling pools • Fitness center & sauna • Tennis & pickleball courts • Billiards room, library & meeting rooms • Picnic areas with grills • Putting green • Fishing pier • Affordable resident-only boat dockage • KAYAK LAUNCH and KAYAK WHICH SELLER WILL BE GIFTING TO THE BUYER. Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key. PROPERTY ENHANCEMENTS & UPDATES: Thoughtfully improved for comfort, reliability, and peace of mind: • NO HURRICANE DAMAGE OR FLOODING • Bosch Washer & Dryer • Newer AC: 12/5/21 • Newer Hot Water Heater: 3/3/17 • New roofs throughout the community • Electrical and plumbing systems updated. A BEAUTIFULLY RENOVATED INTERIOR THAT CREATES THE ULTIMATE COASTAL LIFESTYLE/ THE MONTHLY HOA FEE INCLUDES HAZARD, HURRICANE AND FLOOD INSURANCE/ RESERVES HAVE BEEN FULLY FUNDED

4350 Chatham Drive Unit Unit E-208, Longboat Key

$15,550,000

Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.

8 Beds ⋅ 10 Baths ⋅ T J Oxford Subdivision SubDv. ⋅ 34228 Zip Code

Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.

6685 Gulf Of Mexico Drive, Longboat Key