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2110 Harbourside Drive Unit 536, Longboat Key

Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips.

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

Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips.

2110 Harbourside Drive Unit 536, Longboat Key

2301 Gulf Of Mexico Drive Unit 91N, Longboat Key

$725,000

One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity to create a beachfront residence tailored to your own vision in this 3BR/2BA, 9th-floor residence at the Islander Club on Longboat Key. From the moment you step through the foyer, the horizon unfolds, revealing sweeping blues and greens that trace the shoreline and stretch across the Gulf, forming a breathtaking backdrop that changes throughout the day. Wood floors flow throughout the residence, complementing the natural palette beyond the glass. The living room is defined by a full wall of sliders that open to an expansive terrace positioned directly above the beach. From here, the sights and sounds of the shoreline become part of daily life. The expansive balcony extends along the Gulf side of the residence, extending the outdoor living space and offering multiple vantage points along the coast. The kitchen features white cabinetry, contrasting black stone countertops, white appliances, and a clean tile backsplash, with a convenient serving window connecting to the living area for easy entertaining. The primary suite offers its own wall of sliders opening to the terrace and uninterrupted views of the beach and Gulf beyond. The second bedroom provides comfortable space for family or visitors, while the flexible layout allows for thoughtful updates that can enhance both style and functionality over time. Set in a prime mid-key location, Islander Club offers a resort-style environment with a beachfront swimming pool, tennis courts, updated clubhouse, fitness center, library, billiards room, and secure gated entry. All just steps from the sand and a short drive to the shopping, dining, and cultural attractions of St. Armands Circle and downtown Sarasota.

3 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code

One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity to create a beachfront residence tailored to your own vision in this 3BR/2BA, 9th-floor residence at the Islander Club on Longboat Key. From the moment you step through the foyer, the horizon unfolds, revealing sweeping blues and greens that trace the shoreline and stretch across the Gulf, forming a breathtaking backdrop that changes throughout the day. Wood floors flow throughout the residence, complementing the natural palette beyond the glass. The living room is defined by a full wall of sliders that open to an expansive terrace positioned directly above the beach. From here, the sights and sounds of the shoreline become part of daily life. The expansive balcony extends along the Gulf side of the residence, extending the outdoor living space and offering multiple vantage points along the coast. The kitchen features white cabinetry, contrasting black stone countertops, white appliances, and a clean tile backsplash, with a convenient serving window connecting to the living area for easy entertaining. The primary suite offers its own wall of sliders opening to the terrace and uninterrupted views of the beach and Gulf beyond. The second bedroom provides comfortable space for family or visitors, while the flexible layout allows for thoughtful updates that can enhance both style and functionality over time. Set in a prime mid-key location, Islander Club offers a resort-style environment with a beachfront swimming pool, tennis courts, updated clubhouse, fitness center, library, billiards room, and secure gated entry. All just steps from the sand and a short drive to the shopping, dining, and cultural attractions of St. Armands Circle and downtown Sarasota.

2301 Gulf Of Mexico Drive Unit 91N, Longboat Key

1065 Gulf Of Mexico Drive Unit 603, Longboat Key

$725,000

Beachplace Penthouse with Gulf Views — Top-Floor Residence with Direct Beach Access Discover an inviting top-floor retreat in Building 10 at Beachplace, offering direct access to the Gulf of Mexico and wide views of the community’s lush landscape, sparkling shoreline, and partial Bay vistas. This furnished 6th-floor residence provides a bright coastal setting, ready for your personal touch. New impact floor-to-ceiling sliders and windows (2024) illuminate the more than 1,500-square-foot layout, bringing natural light into the open living and dining areas and connecting seamlessly to the beach-to-bay terrace. The kitchen sits at the center of the home and offers an efficient design with eating space, breakfast bar seating, and laundry closet. The split-bedroom layout enhances privacy. The primary suite includes terrace access, built-in closet with dressing area, and an en-suite bath. The guest suite, located on the opposite side of the residence, is positioned to enhance privacy. Additional conveniences include one under-building parking space (deeded, covered) plus additional outside parking, and generous storage. Beachplace is a gated Gulf-front community known for resort amenities and well-managed operations. Residents enjoy 24-hour security, on-site management, a large clubhouse, fitness center, tennis courts, walking paths, and a Gulf-side sundeck with heated pool and spa. A private boardwalk leads directly to the beach. The community’s amenities also include a spa, sauna, meeting rooms, and beautifully maintained grounds. Ideally positioned along the southern end of Longboat Key, this residence places you minutes from the island’s best recreation and conveniences. Enjoy nearby marinas, championship golf at the Longboat Key Club, waterfront dining, and the boutiques of St. Armands Circle. Downtown Sarasota—home to world-class arts, theaters, galleries, and the Bayfront Park—lies just over the bridge. With wide beaches, tropical landscaping, and exceptional amenities, Beachplace offers an effortless coastal lifestyle in one of Sarasota’s most desirable Gulf-front settings.

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

Beachplace Penthouse with Gulf Views — Top-Floor Residence with Direct Beach Access Discover an inviting top-floor retreat in Building 10 at Beachplace, offering direct access to the Gulf of Mexico and wide views of the community’s lush landscape, sparkling shoreline, and partial Bay vistas. This furnished 6th-floor residence provides a bright coastal setting, ready for your personal touch. New impact floor-to-ceiling sliders and windows (2024) illuminate the more than 1,500-square-foot layout, bringing natural light into the open living and dining areas and connecting seamlessly to the beach-to-bay terrace. The kitchen sits at the center of the home and offers an efficient design with eating space, breakfast bar seating, and laundry closet. The split-bedroom layout enhances privacy. The primary suite includes terrace access, built-in closet with dressing area, and an en-suite bath. The guest suite, located on the opposite side of the residence, is positioned to enhance privacy. Additional conveniences include one under-building parking space (deeded, covered) plus additional outside parking, and generous storage. Beachplace is a gated Gulf-front community known for resort amenities and well-managed operations. Residents enjoy 24-hour security, on-site management, a large clubhouse, fitness center, tennis courts, walking paths, and a Gulf-side sundeck with heated pool and spa. A private boardwalk leads directly to the beach. The community’s amenities also include a spa, sauna, meeting rooms, and beautifully maintained grounds. Ideally positioned along the southern end of Longboat Key, this residence places you minutes from the island’s best recreation and conveniences. Enjoy nearby marinas, championship golf at the Longboat Key Club, waterfront dining, and the boutiques of St. Armands Circle. Downtown Sarasota—home to world-class arts, theaters, galleries, and the Bayfront Park—lies just over the bridge. With wide beaches, tropical landscaping, and exceptional amenities, Beachplace offers an effortless coastal lifestyle in one of Sarasota’s most desirable Gulf-front settings.

1065 Gulf Of Mexico Drive Unit 603, Longboat Key

2800 Harbourside Drive Drive Unit D-19 D-20, Longboat Key

$725,000

A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, restaurant, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet.

Bay Isles SubDv. ⋅ 34228 Zip Code

A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, restaurant, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet.

2800 Harbourside Drive Drive Unit D-19 D-20, Longboat Key

2020 Harbourside Drive Unit 457, Longboat Key

$724,000

Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately.

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

Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately.

2020 Harbourside Drive Unit 457, Longboat Key

1965 Gulf Of Mexico Drive Unit G5-407, Longboat Key

$720,000

BEACHFRONT CONDO with FANTASTIC BEACH & GULF VIEW. Enjoy coastal living at its best in this beautifully updated 2-bedroom, 2-bath condo with 1,257 sq ft under air, located on the fourth floor of the highly sought-after Seaplace Community on Longboat Key. This residence offers fantastic Gulf and beach views, higher ceiling height than many units, and a screened lanai where you can relax with refreshing sea breezes and sparkling water views. Inside, you’ll find newer appliances, kitchen backsplash, wood flooring throughout the kitchen, living room, second bedroom, and second bathroom, a newer water heater, Murphy bed, folding doors in the second bedroom, updated ceiling trim in the living room, and fresh interior paint completed about a year ago. Seaplace is a gated, resort-style beachfront community known for its lush landscaping and outstanding amenities, including direct beach access, two heated pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, a one-mile walking trail, and a remodeled clubhouse with fitness center, sauna, library, and Gulf-view patio with BBQ grills, along with 24-hour guard-gated security and on-site management. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this condo is perfect as a vacation home, investment property, or full-time residence, offering an exceptional blend of comfort, convenience, and beachfront lifestyle.

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

BEACHFRONT CONDO with FANTASTIC BEACH & GULF VIEW. Enjoy coastal living at its best in this beautifully updated 2-bedroom, 2-bath condo with 1,257 sq ft under air, located on the fourth floor of the highly sought-after Seaplace Community on Longboat Key. This residence offers fantastic Gulf and beach views, higher ceiling height than many units, and a screened lanai where you can relax with refreshing sea breezes and sparkling water views. Inside, you’ll find newer appliances, kitchen backsplash, wood flooring throughout the kitchen, living room, second bedroom, and second bathroom, a newer water heater, Murphy bed, folding doors in the second bedroom, updated ceiling trim in the living room, and fresh interior paint completed about a year ago. Seaplace is a gated, resort-style beachfront community known for its lush landscaping and outstanding amenities, including direct beach access, two heated pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, a one-mile walking trail, and a remodeled clubhouse with fitness center, sauna, library, and Gulf-view patio with BBQ grills, along with 24-hour guard-gated security and on-site management. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this condo is perfect as a vacation home, investment property, or full-time residence, offering an exceptional blend of comfort, convenience, and beachfront lifestyle.

1965 Gulf Of Mexico Drive Unit G5-407, Longboat Key

2110 Harbourside Drive Unit 522, Longboat Key

$715,000

This Atrium unit in Building Five of Fairway Bay built in 1988 is behind the gates of and walking distance to the Longboat Key Club & Resort Bayside. It is a three/bedroom, two/bathroom turnkey-furnished unit on the second floor but on the third level of the building and has direct Sarasota Bay views from the living area and the primary bedroom suite. It has 2,039 square feet of air-conditioned space and 200 square feet of exterior covered balcony, as well as both the other bedrooms have glass-blocked enclosed smaller balconies. This unit features a brand new 3.5 ton Trane HVAC system and a brand new electrical panel both in April of 2025. All after storm assessments and the upcoming landscape assessment has been and will be paid by the seller. There is a private, locked and gated entry foyer off the second floor walkway. The unit has a foyer entry also and as soon as you step inside, you see the bay. The large Kitchen with newer appliances and newer Corian countertops is across from the foyer. Both open to the large Living Room/Dining Room combination. Guest Bedroom one is to the left of the front door entry and Bedroom two, which is being used as an office/den/study is next to it with bathroom two between both. Both other bedrooms have walk-in closets. To the right of the Living Room/Dining Room area is a hallway with walk-in laundry room with washer/dryer, utility sink, HVAC system and the newer 2023 hot water heater. At the end of this hallway is the primary suite with the primary bathroom, with separate new tile shower stall and a separate newly enclosed tile bathtub and dual sinks. All the sliding glass doors facing the bay have newer manual hurricane shutters. Everything that you see, you get and this unit is in move-in condition right now. No dogs are allowed in Building Five, only cats are allowed. Your 16 x 20 foot parking space under the building on the ground floor #519 is assigned and covered. There is also 4 x 10 extra feet in front of it to the garage wall. There is also a deeded and 5 x 12 assigned storage room across from the parking space. The Atrium has a private pool between building five and building six. The rental restrictions are a one month minimum, once a year. This address is 2110 Harbourside Drive. The community has its own community swimming pool, clubhouse, and newly enlarged and redone fitness center all close by at 2018 Harbourside Drive. There is a deeded beach access across the street with 600 feet on beach on the Gulf of Mexico that can be accessed by walking, biking or driving with plenty of parking, a gazebo, shaded areas, grills (bring your own charcoal), seating, dining, restrooms and showers for your use 24/7. This is an estate sale and ready for you to buy.

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

This Atrium unit in Building Five of Fairway Bay built in 1988 is behind the gates of and walking distance to the Longboat Key Club & Resort Bayside. It is a three/bedroom, two/bathroom turnkey-furnished unit on the second floor but on the third level of the building and has direct Sarasota Bay views from the living area and the primary bedroom suite. It has 2,039 square feet of air-conditioned space and 200 square feet of exterior covered balcony, as well as both the other bedrooms have glass-blocked enclosed smaller balconies. This unit features a brand new 3.5 ton Trane HVAC system and a brand new electrical panel both in April of 2025. All after storm assessments and the upcoming landscape assessment has been and will be paid by the seller. There is a private, locked and gated entry foyer off the second floor walkway. The unit has a foyer entry also and as soon as you step inside, you see the bay. The large Kitchen with newer appliances and newer Corian countertops is across from the foyer. Both open to the large Living Room/Dining Room combination. Guest Bedroom one is to the left of the front door entry and Bedroom two, which is being used as an office/den/study is next to it with bathroom two between both. Both other bedrooms have walk-in closets. To the right of the Living Room/Dining Room area is a hallway with walk-in laundry room with washer/dryer, utility sink, HVAC system and the newer 2023 hot water heater. At the end of this hallway is the primary suite with the primary bathroom, with separate new tile shower stall and a separate newly enclosed tile bathtub and dual sinks. All the sliding glass doors facing the bay have newer manual hurricane shutters. Everything that you see, you get and this unit is in move-in condition right now. No dogs are allowed in Building Five, only cats are allowed. Your 16 x 20 foot parking space under the building on the ground floor #519 is assigned and covered. There is also 4 x 10 extra feet in front of it to the garage wall. There is also a deeded and 5 x 12 assigned storage room across from the parking space. The Atrium has a private pool between building five and building six. The rental restrictions are a one month minimum, once a year. This address is 2110 Harbourside Drive. The community has its own community swimming pool, clubhouse, and newly enlarged and redone fitness center all close by at 2018 Harbourside Drive. There is a deeded beach access across the street with 600 feet on beach on the Gulf of Mexico that can be accessed by walking, biking or driving with plenty of parking, a gazebo, shaded areas, grills (bring your own charcoal), seating, dining, restrooms and showers for your use 24/7. This is an estate sale and ready for you to buy.

2110 Harbourside Drive Unit 522, Longboat Key

4805 Gulf Of Mexico Drive Unit 105, Longboat Key

$705,000

Experience direct Gulf-front living in this turnkey-furnished, first-floor walkout residence at The Westchester on Longboat Key. Enjoy turquoise water views from nearly every room, with miles of pristine beach just outside your door. This two-bedroom, two-bath condominium is tastefully decorated in a coastal style and features a spacious split floor plan designed for comfort and privacy, along with seamless indoor-outdoor access to the pool and beach. The living and dining areas include a built-in entertainment center and serving buffet. The kitchen is appointed with stainless steel appliances, generous counter space, and abundant storage. Both bedrooms offer en suite baths and generous walk-in closets, with additional storage in dual closet spaces. The primary suite includes a private screened lanai overlooking the Gulf, and there is an in-unit washer and dryer for added convenience. A larger screened lanai off the great room frames panoramic Gulf views and opens directly to the community pool and pristine shoreline. This well-designed and fully furnished unit includes assigned covered parking and invites you to enjoy effortless coastal living. Community amenities include lighted tennis and pickleball courts, a basketball court, two heated pools, shuffleboard, outdoor grills and cabanas, kayak and bicycle storage, and generous private storage lockers for beach gear. A newly renovated clubhouse is coming soon, featuring a full kitchen, lending library, and fitness area. Rentals are permitted, offering flexibility for seasonal or year-round use. The Westchester’s mid-key location offers convenient proximity to Bayfront Park with its dog parks, as well as to nearby Publix supermarket, pharmacy, banking, and fitness facilities. Residents are also within minutes of the Centre Shops, Whitney Plaza Shops, and popular north-end waterfront dining, including bayside favorites like Shore Restaurant and Mar Vista. Longboat Key offers a private golf course, full-service marina, waterfront parks, and a variety of dining options. Nearby destinations include St. Armands Circle and downtown Sarasota.

2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code

Experience direct Gulf-front living in this turnkey-furnished, first-floor walkout residence at The Westchester on Longboat Key. Enjoy turquoise water views from nearly every room, with miles of pristine beach just outside your door. This two-bedroom, two-bath condominium is tastefully decorated in a coastal style and features a spacious split floor plan designed for comfort and privacy, along with seamless indoor-outdoor access to the pool and beach. The living and dining areas include a built-in entertainment center and serving buffet. The kitchen is appointed with stainless steel appliances, generous counter space, and abundant storage. Both bedrooms offer en suite baths and generous walk-in closets, with additional storage in dual closet spaces. The primary suite includes a private screened lanai overlooking the Gulf, and there is an in-unit washer and dryer for added convenience. A larger screened lanai off the great room frames panoramic Gulf views and opens directly to the community pool and pristine shoreline. This well-designed and fully furnished unit includes assigned covered parking and invites you to enjoy effortless coastal living. Community amenities include lighted tennis and pickleball courts, a basketball court, two heated pools, shuffleboard, outdoor grills and cabanas, kayak and bicycle storage, and generous private storage lockers for beach gear. A newly renovated clubhouse is coming soon, featuring a full kitchen, lending library, and fitness area. Rentals are permitted, offering flexibility for seasonal or year-round use. The Westchester’s mid-key location offers convenient proximity to Bayfront Park with its dog parks, as well as to nearby Publix supermarket, pharmacy, banking, and fitness facilities. Residents are also within minutes of the Centre Shops, Whitney Plaza Shops, and popular north-end waterfront dining, including bayside favorites like Shore Restaurant and Mar Vista. Longboat Key offers a private golf course, full-service marina, waterfront parks, and a variety of dining options. Nearby destinations include St. Armands Circle and downtown Sarasota.

4805 Gulf Of Mexico Drive Unit 105, Longboat Key

4600 Gulf Of Mexico Drive Unit 206, Longboat Key

$701,000

$50,000 PRICE IMPROVEMENT – Exceptional Luxury Bayfront Value on Longboat Key! Now offered at an incredible new price, this beautifully updated large END-UNIT condo presents a rare opportunity to own premier bayfront living in Windward Bay. Experience elevated Longboat Key bayfront living in this BEAUTIFULLY UPDATED and impeccably maintained 2-bedroom, 2-bathroom corner END-UNIT condo in the sought-after Windward Bay community. This ELEGANT RESIDENCE offers unobstructed full Sarasota Bay VIEWS from nearly every room through dramatic floor-to-ceiling windows. Exceptionally PRIVATE and boasting the LARGEST FLOOR PLAN in the community, this condo is located on the second floor with convenient elevator access - perfectly blending comfort, sophistication and coastal serenity. The open-concept kitchen features Italian quartz countertops, stainless steel appliances, a large breakfast island and 42"cabinetry with elegant, iridescent Mother-of-Pearl backsplash that flows seamlessly into the great room with tranquil water views. PORCELAIN tile flooring THROUGHOUT enhances the modern coastal aesthetic. The bayfront primary suite is a peaceful retreat and offers direct lanai access, a generous walk-in closet, and a luxurious ensuite bath with custom walk-in shower and dual-sink vanity. The second bedroom also enjoys bay views and lanai access, making it ideal for guests or a home office, and sits adjacent to updated guest bathroom. Additional conveniences include brand new in-unit laundry, private storage, and under-building parking. Recent upgrades include PGT hurricane-impact windows, including a premium, single pane panoramic window in the great room, a 2021 HVAC system, and a 2020 water heater. The monthly HOA fee of $1,325 includes hazard, hurricane and flood insurance, recreational amenities and FULLY FUNDED RESERVES - major value for bayfront condo ownership. There is a modest assessment $293 per month at a low interest rate. Windward Bay spans 26 acres of waterfront and offers resort-style amenities including BOAT SLIPS, kayak storage, three private beach access points, two heated pools, a fitness center, saunas, tennis and pickleball courts, walking paths, BBQ grills, fire pits, and a clubhouse. The community is PET FRIENDLY, allowing two pets up to 75 lbs each, and approved renter pets, making this an excellent primary residence, vacation home, or investment property. Located mid-island, you are minutes from championship golf, full-service marinas, St. Armands Circle, downtown Sarasota, and Anna Maria Island. Whether you are seeking a luxury Longboat Key waterfront condo, a serene island retreat or a strong rental opportunity, this exceptional bayfront residence delivers the ultimate coastal lifestyle!

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

$50,000 PRICE IMPROVEMENT – Exceptional Luxury Bayfront Value on Longboat Key! Now offered at an incredible new price, this beautifully updated large END-UNIT condo presents a rare opportunity to own premier bayfront living in Windward Bay. Experience elevated Longboat Key bayfront living in this BEAUTIFULLY UPDATED and impeccably maintained 2-bedroom, 2-bathroom corner END-UNIT condo in the sought-after Windward Bay community. This ELEGANT RESIDENCE offers unobstructed full Sarasota Bay VIEWS from nearly every room through dramatic floor-to-ceiling windows. Exceptionally PRIVATE and boasting the LARGEST FLOOR PLAN in the community, this condo is located on the second floor with convenient elevator access - perfectly blending comfort, sophistication and coastal serenity. The open-concept kitchen features Italian quartz countertops, stainless steel appliances, a large breakfast island and 42"cabinetry with elegant, iridescent Mother-of-Pearl backsplash that flows seamlessly into the great room with tranquil water views. PORCELAIN tile flooring THROUGHOUT enhances the modern coastal aesthetic. The bayfront primary suite is a peaceful retreat and offers direct lanai access, a generous walk-in closet, and a luxurious ensuite bath with custom walk-in shower and dual-sink vanity. The second bedroom also enjoys bay views and lanai access, making it ideal for guests or a home office, and sits adjacent to updated guest bathroom. Additional conveniences include brand new in-unit laundry, private storage, and under-building parking. Recent upgrades include PGT hurricane-impact windows, including a premium, single pane panoramic window in the great room, a 2021 HVAC system, and a 2020 water heater. The monthly HOA fee of $1,325 includes hazard, hurricane and flood insurance, recreational amenities and FULLY FUNDED RESERVES - major value for bayfront condo ownership. There is a modest assessment $293 per month at a low interest rate. Windward Bay spans 26 acres of waterfront and offers resort-style amenities including BOAT SLIPS, kayak storage, three private beach access points, two heated pools, a fitness center, saunas, tennis and pickleball courts, walking paths, BBQ grills, fire pits, and a clubhouse. The community is PET FRIENDLY, allowing two pets up to 75 lbs each, and approved renter pets, making this an excellent primary residence, vacation home, or investment property. Located mid-island, you are minutes from championship golf, full-service marinas, St. Armands Circle, downtown Sarasota, and Anna Maria Island. Whether you are seeking a luxury Longboat Key waterfront condo, a serene island retreat or a strong rental opportunity, this exceptional bayfront residence delivers the ultimate coastal lifestyle!

4600 Gulf Of Mexico Drive Unit 206, Longboat Key

$700,000

This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect blend of classy with a modern flair. Before entering the home take note of the huge 16’ x 13’ outdoor deck where you can enjoy a partial view of the Gulf. It's a great place to start your day with a cup of morning coffee, or enjoy a nice meal in the evening, and catch the spectacular colors of the sky as the sun sets! Step inside to this inviting, beautifully appointed 2-bedroom 2-bath condominium with luxury vinyl flooring and crown molding throughout. The entire living/ dining areas, lanai, both bedrooms and second bathroom have all been recently updated. Giving the condo a fresh polished appearance accentuated by recessed glass display shelving and an abundance of recessed lights. The depth of workmanship in the updates carries onto the stylized door moldings into the primary bedroom. All popcorn has been removed! The kitchen offers a coffee bar, stainless steel appliances, a pantry, a nice arrangement of cabinets, and granite countertops open to the dining room and living room, perfect for entertaining. Take in the view of the lush tropical landscape and gorgeous pond right below the lanai that is open to the living room. Perfect for a Murphy bed, extra living space, a reading nook or your second favorite spot for your morning coffee as the sun rises. The primary bedroom offers an additional 6’ by 6’ area that is perfect for an office desk looking out over nature. The primary also offers a walk-in closet and a generously sized ensuite bath with dual vanities. Bayport Beach & Tennis Club is a gem with 27 tropical landscaped acres and 1200 feet of private Gulf waterfront deeded access. Where you can grab a chair and umbrella and soak up the sun, or take in the breathtaking sunsets. Enjoy Sarasota Bay just outside your door and stroll to the private dock where you can fish, kayak, paddleboard, and watch for the manatees and dolphins as they cruise by. This community also offers a clubhouse, fitness center, 4 Har-Ter tennis courts, golf practice net, and a Junior-Olympic heated pool. Bayport Beach & Tennis Club consists of 17 buildings built between 1979 and 1983. Designed by architect Tim Seibert of the Sarasota School of Architecture. Located mid-key with a wealth of attractions moments away, including Bayfront Park, steps away, offering Pickle Ball, Basketball, Shuffleboard courts, playground, bike paths, kayak launch and Publix 2 miles away.

2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code

This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect blend of classy with a modern flair. Before entering the home take note of the huge 16’ x 13’ outdoor deck where you can enjoy a partial view of the Gulf. It's a great place to start your day with a cup of morning coffee, or enjoy a nice meal in the evening, and catch the spectacular colors of the sky as the sun sets! Step inside to this inviting, beautifully appointed 2-bedroom 2-bath condominium with luxury vinyl flooring and crown molding throughout. The entire living/ dining areas, lanai, both bedrooms and second bathroom have all been recently updated. Giving the condo a fresh polished appearance accentuated by recessed glass display shelving and an abundance of recessed lights. The depth of workmanship in the updates carries onto the stylized door moldings into the primary bedroom. All popcorn has been removed! The kitchen offers a coffee bar, stainless steel appliances, a pantry, a nice arrangement of cabinets, and granite countertops open to the dining room and living room, perfect for entertaining. Take in the view of the lush tropical landscape and gorgeous pond right below the lanai that is open to the living room. Perfect for a Murphy bed, extra living space, a reading nook or your second favorite spot for your morning coffee as the sun rises. The primary bedroom offers an additional 6’ by 6’ area that is perfect for an office desk looking out over nature. The primary also offers a walk-in closet and a generously sized ensuite bath with dual vanities. Bayport Beach & Tennis Club is a gem with 27 tropical landscaped acres and 1200 feet of private Gulf waterfront deeded access. Where you can grab a chair and umbrella and soak up the sun, or take in the breathtaking sunsets. Enjoy Sarasota Bay just outside your door and stroll to the private dock where you can fish, kayak, paddleboard, and watch for the manatees and dolphins as they cruise by. This community also offers a clubhouse, fitness center, 4 Har-Ter tennis courts, golf practice net, and a Junior-Olympic heated pool. Bayport Beach & Tennis Club consists of 17 buildings built between 1979 and 1983. Designed by architect Tim Seibert of the Sarasota School of Architecture. Located mid-key with a wealth of attractions moments away, including Bayfront Park, steps away, offering Pickle Ball, Basketball, Shuffleboard courts, playground, bike paths, kayak launch and Publix 2 miles away.

706 Bayport Way Unit 706, Longboat Key

350 Gulf Of Mexico Drive Unit 234, Longboat Key

$700,000

Virtually Staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces highlight scenic views and offer the option of installing a gas grill. Inside, soaring two-story ceilings define the main living area, creating an airy, light-filled atmosphere enhanced by expansive windows that frame picturesque views of the lagoon, resort-style pool w/ waterfall features, tropical plantings and the waters of Sarasota Bay and distant city skyline. The open living and dining spaces are ideal for both relaxed everyday living and entertaining, anchored by a fireplace and generous wall space for art. From the entry patio, unexpected Bay and city views provide a striking first impression and a unique urban-meets-coastal backdrop. The residence features three full bedrooms and three and a half baths. The upper-level retreat with its full bath has a terrace with elevated views across the natural preserve toward the city. This home presents a true blank canvas, thoughtfully priced to allow the new owner to reimagine and transform it into their own vision of refined coastal living. A deeded, private two-car garage adds exceptional convenience and value—an uncommon and highly desirable feature. Located on the coveted south end of Longboat Key, Tangerine Bay Club is a gated, pet-friendly community close to Lido Beach, dining and boutique shopping on St. Armands Circle, and the cultural, dining, and arts scene of downtown Sarasota. Optional Bay Isles Beach Club membership is available, providing exclusive access to a private, gated four-acre Gulf of Mexico beach facility, reserved for a select group of members—ideal for beach gatherings, sunset celebrations, and effortless days by the sea. An outstanding opportunity to embrace the Florida lifestyle in one of Longboat Key’s most desirable bayfront communities.

3 Beds ⋅ 4 Baths ⋅ Tangerine Bay Club SubDv. ⋅ 34228 Zip Code

Virtually Staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces highlight scenic views and offer the option of installing a gas grill. Inside, soaring two-story ceilings define the main living area, creating an airy, light-filled atmosphere enhanced by expansive windows that frame picturesque views of the lagoon, resort-style pool w/ waterfall features, tropical plantings and the waters of Sarasota Bay and distant city skyline. The open living and dining spaces are ideal for both relaxed everyday living and entertaining, anchored by a fireplace and generous wall space for art. From the entry patio, unexpected Bay and city views provide a striking first impression and a unique urban-meets-coastal backdrop. The residence features three full bedrooms and three and a half baths. The upper-level retreat with its full bath has a terrace with elevated views across the natural preserve toward the city. This home presents a true blank canvas, thoughtfully priced to allow the new owner to reimagine and transform it into their own vision of refined coastal living. A deeded, private two-car garage adds exceptional convenience and value—an uncommon and highly desirable feature. Located on the coveted south end of Longboat Key, Tangerine Bay Club is a gated, pet-friendly community close to Lido Beach, dining and boutique shopping on St. Armands Circle, and the cultural, dining, and arts scene of downtown Sarasota. Optional Bay Isles Beach Club membership is available, providing exclusive access to a private, gated four-acre Gulf of Mexico beach facility, reserved for a select group of members—ideal for beach gatherings, sunset celebrations, and effortless days by the sea. An outstanding opportunity to embrace the Florida lifestyle in one of Longboat Key’s most desirable bayfront communities.

350 Gulf Of Mexico Drive Unit 234, Longboat Key

1975 Gulf Of Mexico Drive Unit G4-309, Longboat Key

$700,000

Rarely available with unobstructed and direct Gulf views unit in the desirable G4 building. Experience true beachfront living in this direct Gulf-front 2-bedroom, 2-bath residence located in the highly desirable Seaplace Community on Longboat Key. This fully updated, move-in-ready condo offers breathtaking direct water, beach, and sunset views, creating a front-row seat to Florida’s most spectacular coastal scenery. The interior features tile flooring throughout, a bright and open layout, and a modern kitchen with stainless steel appliances, making it easy to enjoy or immediately place into service as a rental. The screened lanai is equipped with a roll-down hurricane shutter, providing added storm protection, peace of mind, and convenience when you’re away. Seaplace is a gated, resort-style beachfront community known for its lush tropical landscaping and outstanding amenities, including direct beach access, two heated swimming pools, a kiddie pool, two hot tubs, three Har-Tru tennis courts, a scenic one-mile walking trail, and a beautifully remodeled clubhouse with fitness center, sauna, library, and Gulf-view patio with BBQ grills. Residents also enjoy 24-hour guard-gated security and on-site management, providing comfort and peace of mind. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this condo is perfect as a vacation home, investment property, or full-time residence, offering an exceptional blend of comfort, convenience, and true beachfront lifestyle.

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

Rarely available with unobstructed and direct Gulf views unit in the desirable G4 building. Experience true beachfront living in this direct Gulf-front 2-bedroom, 2-bath residence located in the highly desirable Seaplace Community on Longboat Key. This fully updated, move-in-ready condo offers breathtaking direct water, beach, and sunset views, creating a front-row seat to Florida’s most spectacular coastal scenery. The interior features tile flooring throughout, a bright and open layout, and a modern kitchen with stainless steel appliances, making it easy to enjoy or immediately place into service as a rental. The screened lanai is equipped with a roll-down hurricane shutter, providing added storm protection, peace of mind, and convenience when you’re away. Seaplace is a gated, resort-style beachfront community known for its lush tropical landscaping and outstanding amenities, including direct beach access, two heated swimming pools, a kiddie pool, two hot tubs, three Har-Tru tennis courts, a scenic one-mile walking trail, and a beautifully remodeled clubhouse with fitness center, sauna, library, and Gulf-view patio with BBQ grills. Residents also enjoy 24-hour guard-gated security and on-site management, providing comfort and peace of mind. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this condo is perfect as a vacation home, investment property, or full-time residence, offering an exceptional blend of comfort, convenience, and true beachfront lifestyle.

1975 Gulf Of Mexico Drive Unit G4-309, Longboat Key

4621 Gulf Of Mexico Drive Unit 14F, Longboat Key

$700,000

Investment Opportunity with low HOA fees! Beautifully updated and decorated two-bedroom, two-bath unit with vaulted ceilings can sleep up to 6 at Casa Del Mar on Longboat Key. Casa Del Mar is a popular beach resort with short-term rentals located directly on the Gulf. Use the condo for your own vacation and enjoy all Longboat Key has to offer while collecting income the rest of the year. This turnkey furnished condo is tiled throughout and offers views of the tropically landscaped courtyard and partial Gulf views from the extended living area. The primary ensuite bedroom is furnished with a king size bed and built-in cabinetry. The guest bedroom is furnished with 2 twin beds, built-in cabinetry with a full bath in the hallway. The kitchen has stone counters, solid wood cabinets and stainless appliances. Community amenities include a huge 30’ x 60’ gulf front heated pool, grill area, tennis, pickleball and basketball. Complimentary beach lounges are provided for guests and umbrella rentals are available. Casa Del Mar’s on-site management handles year-round bookings along with all the details so you can enjoy your investment stress-free. Annual gross income for #14F: 2023 $45,131, 2024 $59,833, and 2025 $56,388. Great location convenient to St Armand’s Circle with shops, fine and casual dining, and entertainment and a short drive over the bridge to the southwest cultural hub of downtown Sarasota.

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

Investment Opportunity with low HOA fees! Beautifully updated and decorated two-bedroom, two-bath unit with vaulted ceilings can sleep up to 6 at Casa Del Mar on Longboat Key. Casa Del Mar is a popular beach resort with short-term rentals located directly on the Gulf. Use the condo for your own vacation and enjoy all Longboat Key has to offer while collecting income the rest of the year. This turnkey furnished condo is tiled throughout and offers views of the tropically landscaped courtyard and partial Gulf views from the extended living area. The primary ensuite bedroom is furnished with a king size bed and built-in cabinetry. The guest bedroom is furnished with 2 twin beds, built-in cabinetry with a full bath in the hallway. The kitchen has stone counters, solid wood cabinets and stainless appliances. Community amenities include a huge 30’ x 60’ gulf front heated pool, grill area, tennis, pickleball and basketball. Complimentary beach lounges are provided for guests and umbrella rentals are available. Casa Del Mar’s on-site management handles year-round bookings along with all the details so you can enjoy your investment stress-free. Annual gross income for #14F: 2023 $45,131, 2024 $59,833, and 2025 $56,388. Great location convenient to St Armand’s Circle with shops, fine and casual dining, and entertainment and a short drive over the bridge to the southwest cultural hub of downtown Sarasota.

4621 Gulf Of Mexico Drive Unit 14F, Longboat Key

$700,000

Lot for sale North end of Longboar key in the Village, Has an existing home on property which is a tear down but you can be the judge. Lot siz 105 x 110. Has view of Sarasota Bay and more when you build up.

Longboat Key SubDv. ⋅ 34228 Zip Code

Lot for sale North end of Longboar key in the Village, Has an existing home on property which is a tear down but you can be the judge. Lot siz 105 x 110. Has view of Sarasota Bay and more when you build up.

7061 Longboat Drive E, Longboat Key

$695,000

Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The centerpiece of the kitchen is the large, strategically custom-designed quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42-inch cabinetry, stainless steel appliances, large undermount sink with a push-button garbage disposal, lovely backsplash and lots of storage with an abundance of additional counter space, ideally designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized, classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9-by-6-foot in villa laundry room with new Electrolux washer and dryer. All hurricane-grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay, with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center, which makes this a useful space. Go outside onto the brick paver patio and lounge, grill and relax with the sound and views of Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, air conditioner in 2020 and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community, which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico, with restaurants you can get to by boat. The Spanish Main maintenance-free community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for affordable leasing. Beach access is ideal for those numerous beach days and magnificent sunsets. This pet-friendly very active 55-plus community are added benefits for your enjoyment. Only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events Sarasota and St. Armands Circle have to offer. Private second-deeded parking place with this villa.

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The centerpiece of the kitchen is the large, strategically custom-designed quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42-inch cabinetry, stainless steel appliances, large undermount sink with a push-button garbage disposal, lovely backsplash and lots of storage with an abundance of additional counter space, ideally designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized, classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9-by-6-foot in villa laundry room with new Electrolux washer and dryer. All hurricane-grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay, with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center, which makes this a useful space. Go outside onto the brick paver patio and lounge, grill and relax with the sound and views of Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, air conditioner in 2020 and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community, which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico, with restaurants you can get to by boat. The Spanish Main maintenance-free community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for affordable leasing. Beach access is ideal for those numerous beach days and magnificent sunsets. This pet-friendly very active 55-plus community are added benefits for your enjoyment. Only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events Sarasota and St. Armands Circle have to offer. Private second-deeded parking place with this villa.

925 Spanish Drive N, Longboat Key

4234 Gulf Of Mexico Drive Unit H1, Longboat Key

$695,000

Gorgeous coastal renovation, waterfront location, deeded beach, pet friendly and more. Enjoy this new, fully renovated two-bedroom, two-bath furnished bayfront condominium in Longboat's Pelican Harbour & Beach Club. Association amenities include private beach, tennis and pickleball courts, heated resort-style pool, clubhouse, kayak launch and owner boat docks. This condominium features include hurricane windows and doors, new air conditioner, engineered hardwood flooring, custom cabinetry, quartz tops, stainless appliances, induction cooking, built-in ovens, bar area with beverage refrigerator and a large center island, all opening to the great room and dining areas. Spacious primary suite features private bath with custom walk-in shower, dual vanity, built-in closets and water views. The guest suite, split from the primary, offers friends and family alike private space with a king-size bed and adjoining bath with a custom walk-in shower, as well. There is plenty of closet space and storage throughout, and an in-unit laundry with matching front-load HE washer and dryer. You'll even find brand new linens, towels, dishware, etc. included. Association quarterlies include on-site maintenance, landscaping, building property, wind, flood and liability insurances, roofs, exterior painting, cable, water, sewer, trash and more. Pelican Harbour also has fully funded reserves and has installed new roofs, new hurricane carports, upgraded pickleball and tennis courts, and offers owner boat docks with electric and water. Pelican's private beach is near the unit and offers stunning sunset and Gulf views, and miles of turquoise waters and crystal sands. You'll also appreciate the convenient mid-island location close to Bayfront Park, restaurants, shopping, places of worship, and easy access to St Armands, Sarasota and Anna Maria. Gorgeous coastal renovation, brand new furnishing, fantastic mid-island location, pet-friendly and one of the best amenity packages on the island. Enjoy Pelican Harbour and Beach Club. Schedule your showing today.

2 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv. ⋅ 34228 Zip Code

Gorgeous coastal renovation, waterfront location, deeded beach, pet friendly and more. Enjoy this new, fully renovated two-bedroom, two-bath furnished bayfront condominium in Longboat's Pelican Harbour & Beach Club. Association amenities include private beach, tennis and pickleball courts, heated resort-style pool, clubhouse, kayak launch and owner boat docks. This condominium features include hurricane windows and doors, new air conditioner, engineered hardwood flooring, custom cabinetry, quartz tops, stainless appliances, induction cooking, built-in ovens, bar area with beverage refrigerator and a large center island, all opening to the great room and dining areas. Spacious primary suite features private bath with custom walk-in shower, dual vanity, built-in closets and water views. The guest suite, split from the primary, offers friends and family alike private space with a king-size bed and adjoining bath with a custom walk-in shower, as well. There is plenty of closet space and storage throughout, and an in-unit laundry with matching front-load HE washer and dryer. You'll even find brand new linens, towels, dishware, etc. included. Association quarterlies include on-site maintenance, landscaping, building property, wind, flood and liability insurances, roofs, exterior painting, cable, water, sewer, trash and more. Pelican Harbour also has fully funded reserves and has installed new roofs, new hurricane carports, upgraded pickleball and tennis courts, and offers owner boat docks with electric and water. Pelican's private beach is near the unit and offers stunning sunset and Gulf views, and miles of turquoise waters and crystal sands. You'll also appreciate the convenient mid-island location close to Bayfront Park, restaurants, shopping, places of worship, and easy access to St Armands, Sarasota and Anna Maria. Gorgeous coastal renovation, brand new furnishing, fantastic mid-island location, pet-friendly and one of the best amenity packages on the island. Enjoy Pelican Harbour and Beach Club. Schedule your showing today.

4234 Gulf Of Mexico Drive Unit H1, Longboat Key

4825 Gulf Of Mexico Drive Unit 105, Longboat Key

$687,000

Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.

2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code

Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.

4825 Gulf Of Mexico Drive Unit 105, Longboat Key

4500 Gulf Of Mexico Drive Unit 3, Longboat Key

$685,000

GORGEOUS BAYFRONT PENTHOUSE VIEWS--RARE TOP FLOOR OPPORTUNITY!! Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living.

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

GORGEOUS BAYFRONT PENTHOUSE VIEWS--RARE TOP FLOOR OPPORTUNITY!! Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living.

4500 Gulf Of Mexico Drive Unit 3, Longboat Key

$684,500

Located in the historic and highly sought-after Longbeach Village at the north end of Longboat Key, this three-bedroom, three-bath block home offers an exceptional opportunity to reimagine an island retreat of timeless beauty. Surrounded by meticulously maintained tropical landscaping, the residence opens to a private backyard oasis complete with a sparkling pool, spa, and cabana, an ideal setting for relaxation or entertaining beneath the swaying palms. Ready for renovation, the home provides a solid foundation for transformation, blending the charm of the Village with the tranquility of coastal living. Just moments from the bay, the Gulf's sugar-sand beaches, the Village's beloved waterfront restaurants, and convenient coffee shops, boutiques and fitness, this property presents a rare opportunity to create your own sanctuary in one of Longboat Key's most cherished neighborhoods.

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

Located in the historic and highly sought-after Longbeach Village at the north end of Longboat Key, this three-bedroom, three-bath block home offers an exceptional opportunity to reimagine an island retreat of timeless beauty. Surrounded by meticulously maintained tropical landscaping, the residence opens to a private backyard oasis complete with a sparkling pool, spa, and cabana, an ideal setting for relaxation or entertaining beneath the swaying palms. Ready for renovation, the home provides a solid foundation for transformation, blending the charm of the Village with the tranquility of coastal living. Just moments from the bay, the Gulf's sugar-sand beaches, the Village's beloved waterfront restaurants, and convenient coffee shops, boutiques and fitness, this property presents a rare opportunity to create your own sanctuary in one of Longboat Key's most cherished neighborhoods.

730 Fox Street, Longboat Key

225 Sands Point Road Unit 7101, Longboat Key

$677,500

Enjoy peaceful lagoon views from this completely remodeled Junior Suite. Sold turnkey furnished and currently in the hotel program, the Junior Suites in this building have 10’ ceilings unlike the other buildings. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace. As an owner in the hotel program you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, spa, fitness center, white sand beach with umbrellas & waitstaff, and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying your Longboat Life today!

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

Enjoy peaceful lagoon views from this completely remodeled Junior Suite. Sold turnkey furnished and currently in the hotel program, the Junior Suites in this building have 10’ ceilings unlike the other buildings. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace. As an owner in the hotel program you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, spa, fitness center, white sand beach with umbrellas & waitstaff, and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying your Longboat Life today!

225 Sands Point Road Unit 7101, Longboat Key

4805 Gulf Of Mexico Drive Unit 103, Longboat Key

$675,000

NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open seamlessly to two screened lanais, and a generously sized guest suite accommodating two double beds. A private laundry room with full-size washer and dryer, two interior storage closets, and a spacious exterior storage unit add exceptional convenience. Offered furnished with select exclusions. Milestone inspections are complete and assessments paid in full—delivering confidence and long-term value. Westchester is an exclusive, impeccably managed beachfront community set on 7 acres with 700 feet of shoreline, featuring two heated pools, beach loungers, tiki huts, pickleball and tennis courts, shuffleboard, BBQ grills, kayak and bicycle storage, and on-site management. A new clubhouse with a fitness center and enhanced Gulf-side pool and landscaping are underway. A rare opportunity for elevated coastal living and investment excellence. CHECK THE VIRTUAL TOUR, and reserve your private viewing

2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code

NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open seamlessly to two screened lanais, and a generously sized guest suite accommodating two double beds. A private laundry room with full-size washer and dryer, two interior storage closets, and a spacious exterior storage unit add exceptional convenience. Offered furnished with select exclusions. Milestone inspections are complete and assessments paid in full—delivering confidence and long-term value. Westchester is an exclusive, impeccably managed beachfront community set on 7 acres with 700 feet of shoreline, featuring two heated pools, beach loungers, tiki huts, pickleball and tennis courts, shuffleboard, BBQ grills, kayak and bicycle storage, and on-site management. A new clubhouse with a fitness center and enhanced Gulf-side pool and landscaping are underway. A rare opportunity for elevated coastal living and investment excellence. CHECK THE VIRTUAL TOUR, and reserve your private viewing

4805 Gulf Of Mexico Drive Unit 103, Longboat Key

$675,000

Introducing a remarkable opportunity to own a piece of paradise at 723 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. This property provides an exceptional opportunity to enjoy all that Longboat Key has to offer, with proximity to sandy shores and a serene environment. As you enter the property, you are greeted by a spacious and functional floor plan that maximizes natural light. The kitchen features modern appliances and ample counter space, making it ideal for both cooking and entertaining. The sleek cabinetry provides a contemporary aesthetic, while the adjoining living and dining area ensures a seamless flow throughout the home, perfect for gatherings with family and friends. The open layout allows for easy interaction between spaces, enhancing the overall living experience. Large windows in the living room capture stunning views and fill the space with sunshine, creating a warm and inviting atmosphere. The combination of warm toned laminate flooring and soft color palettes contributes to the property’s relaxed elegance. Outdoor amenities include well-maintained landscaping that enhances the overall curb appeal of the property. The outdoor areas are perfect for enjoying Florida’s inviting climate. Whether you’re lounging in the garden or taking a short walk to the beach, this location offers a unique coastal lifestyle. This residence is not just a home—it’s a beachside retreat that promises tranquility and leisure. With its close proximity to the water and the conveniences of Longboat Key, this property presents a rare opportunity for those looking to embrace the Florida lifestyle. Schedule a visit today to explore all the potential that 723 Bayport Way has to offer.

2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code

Introducing a remarkable opportunity to own a piece of paradise at 723 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. This property provides an exceptional opportunity to enjoy all that Longboat Key has to offer, with proximity to sandy shores and a serene environment. As you enter the property, you are greeted by a spacious and functional floor plan that maximizes natural light. The kitchen features modern appliances and ample counter space, making it ideal for both cooking and entertaining. The sleek cabinetry provides a contemporary aesthetic, while the adjoining living and dining area ensures a seamless flow throughout the home, perfect for gatherings with family and friends. The open layout allows for easy interaction between spaces, enhancing the overall living experience. Large windows in the living room capture stunning views and fill the space with sunshine, creating a warm and inviting atmosphere. The combination of warm toned laminate flooring and soft color palettes contributes to the property’s relaxed elegance. Outdoor amenities include well-maintained landscaping that enhances the overall curb appeal of the property. The outdoor areas are perfect for enjoying Florida’s inviting climate. Whether you’re lounging in the garden or taking a short walk to the beach, this location offers a unique coastal lifestyle. This residence is not just a home—it’s a beachside retreat that promises tranquility and leisure. With its close proximity to the water and the conveniences of Longboat Key, this property presents a rare opportunity for those looking to embrace the Florida lifestyle. Schedule a visit today to explore all the potential that 723 Bayport Way has to offer.

723 Bayport Way Unit 723, Longboat Key

5125 Gulf Of Mexico Drive Unit 4, Longboat Key

$675,000

An exceptional opportunity to own a private family retreat on the pristine shores of Longboat Key—while generating rental income when you’re away. Located within the intimate beachfront enclave of Sea Grape Inn, this unique resort community offers just eight residences, creating a peaceful, uncrowded atmosphere rarely found on the island. Approved for daily, weekly, or monthly rentals, the property provides excellent flexibility for both personal enjoyment and investment potential. From the moment you arrive, the difference is clear. Each residence is thoughtfully appointed and lives more like a private coastal home than a typical vacation rental. This beautifully maintained condo features stone countertops, updated cabinetry, abundant appliances, and tile flooring throughout. The screened porch serves as a tranquil retreat—perfect for enjoying gentle Gulf breezes, spectacular sunsets, and lush tropical landscaping. Step outside to enjoy the heated beachfront pool overlooking the Gulf—an ideal setting for relaxing swims while taking in sweeping water views. The uncrowded beach is just beyond, with chairs provided for effortless seaside enjoyment. Additional amenities include on-site laundry, a BBQ gazebo area, beach towels, and internet service—everything needed for a seamless coastal getaway. Professional on-site management handles all rentals, marketing, cleaning, bookkeeping, and administrative details, offering truly turnkey ownership with no hidden charges. The residence is being offered turnkey furnished, ready for immediate enjoyment or continued rental success. Ideally situated near local restaurants, nature trails, parks with tennis and pickleball, and convenient shopping, this property combines privacy with accessibility. Financials are available upon request. The condo enjoys strong rental demand; showings will be accommodated with 24-hour notice and guest approval. Please contact the listing agent for availability. Life truly is better on Longboat Key!

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

An exceptional opportunity to own a private family retreat on the pristine shores of Longboat Key—while generating rental income when you’re away. Located within the intimate beachfront enclave of Sea Grape Inn, this unique resort community offers just eight residences, creating a peaceful, uncrowded atmosphere rarely found on the island. Approved for daily, weekly, or monthly rentals, the property provides excellent flexibility for both personal enjoyment and investment potential. From the moment you arrive, the difference is clear. Each residence is thoughtfully appointed and lives more like a private coastal home than a typical vacation rental. This beautifully maintained condo features stone countertops, updated cabinetry, abundant appliances, and tile flooring throughout. The screened porch serves as a tranquil retreat—perfect for enjoying gentle Gulf breezes, spectacular sunsets, and lush tropical landscaping. Step outside to enjoy the heated beachfront pool overlooking the Gulf—an ideal setting for relaxing swims while taking in sweeping water views. The uncrowded beach is just beyond, with chairs provided for effortless seaside enjoyment. Additional amenities include on-site laundry, a BBQ gazebo area, beach towels, and internet service—everything needed for a seamless coastal getaway. Professional on-site management handles all rentals, marketing, cleaning, bookkeeping, and administrative details, offering truly turnkey ownership with no hidden charges. The residence is being offered turnkey furnished, ready for immediate enjoyment or continued rental success. Ideally situated near local restaurants, nature trails, parks with tennis and pickleball, and convenient shopping, this property combines privacy with accessibility. Financials are available upon request. The condo enjoys strong rental demand; showings will be accommodated with 24-hour notice and guest approval. Please contact the listing agent for availability. Life truly is better on Longboat Key!

5125 Gulf Of Mexico Drive Unit 4, Longboat Key

4900 Gulf Of Mexico Drive Unit 203, Longboat Key

$671,500

A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!

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

A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!

4900 Gulf Of Mexico Drive Unit 203, Longboat Key

4900 Gulf Of Mexico Drive Unit 205, Longboat Key

$670,000

Breathtaking full bay views greet you as you enter this delightful 2 Bedroom 2 bath condo at Windward Bay. The interior has been freshly painted and fully updated with brand new Luxury Vinyl Plank flooring and Moen plumbing fixtures. The Unit boasts granite countertops and Brookhill custom wood cabinets in kitchen and baths, GE Profile double oven, Bosch stacking washer/dryer, Hunter Douglas window treatments, large walk-in master bed closet, hurricane impact windows, and Honeywell WiFi thermostat with humidity control. Enjoy the stunning waterfront views as you dine or relax on your private lanai. Windward Bay is a low density, pet friendly community nestled on 26 acres with 1/2 mile of waterfront trails and 3 adjacent beach accesses. (1deeded,2public). It enjoys a prime mid key location near dining, shopping, and world class entertainment in St Armand's Circle, Sarasota, and Anna Maria Island. The property has many recent updates including new roofs, painting of the mid-rises and extensive landscaping. Its numerous amenities include 2 heated pools, tennis and pickleball courts, 2 marinas with 28 boat slips, kayak racks and launches, covered parking, grills, firepits, and seating areas throughout, and a clubhouse with kitchen, meeting room, fitness center, 2 saunas, and a library. One of the very few units at Windward Bay with ALL of its assessments having been fully paid, including the 15 year Community Capital Improvement and the 30 year Longboat Key undergrounding. For added security, the State of Florida Milestone Inspection on all buildings is complete and Windward Bay is certified for an additional 10 years. Whether your're considering a getaway, a new home, or a rental property, don't miss this great opportunity to own your piece of paradise.

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

Breathtaking full bay views greet you as you enter this delightful 2 Bedroom 2 bath condo at Windward Bay. The interior has been freshly painted and fully updated with brand new Luxury Vinyl Plank flooring and Moen plumbing fixtures. The Unit boasts granite countertops and Brookhill custom wood cabinets in kitchen and baths, GE Profile double oven, Bosch stacking washer/dryer, Hunter Douglas window treatments, large walk-in master bed closet, hurricane impact windows, and Honeywell WiFi thermostat with humidity control. Enjoy the stunning waterfront views as you dine or relax on your private lanai. Windward Bay is a low density, pet friendly community nestled on 26 acres with 1/2 mile of waterfront trails and 3 adjacent beach accesses. (1deeded,2public). It enjoys a prime mid key location near dining, shopping, and world class entertainment in St Armand's Circle, Sarasota, and Anna Maria Island. The property has many recent updates including new roofs, painting of the mid-rises and extensive landscaping. Its numerous amenities include 2 heated pools, tennis and pickleball courts, 2 marinas with 28 boat slips, kayak racks and launches, covered parking, grills, firepits, and seating areas throughout, and a clubhouse with kitchen, meeting room, fitness center, 2 saunas, and a library. One of the very few units at Windward Bay with ALL of its assessments having been fully paid, including the 15 year Community Capital Improvement and the 30 year Longboat Key undergrounding. For added security, the State of Florida Milestone Inspection on all buildings is complete and Windward Bay is certified for an additional 10 years. Whether your're considering a getaway, a new home, or a rental property, don't miss this great opportunity to own your piece of paradise.

4900 Gulf Of Mexico Drive Unit 205, Longboat Key

2120 Harbourside Drive Unit 612, Longboat Key

$655,000

It's all about location. Close to everything. Away from it all. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This single-story traditional condominium makes the most of its spaciously designed 2,105 square feet with open-plan living, three bedrooms, two full bathrooms, 30-foot balcony, and under-building parking and storage space. The bayside-inspired interior creates feelings of tranquility and hospitality throughout. The main living space enjoys abundant natural light and bay views from 9-foot sliding glass doors opening onto the balcony. The kitchen opens to the dining and living areas for effortless entertaining with added dining alfresco on the balcony. Wake up to views of the bay from the primary bedroom and just renovated en-suite bath offering peace in a soaking tub and spacious dual vanities. Completing the primary suite are separate spatial his and hers walk-in closets. Two guest wings, each with walk-in closets for added storage, extend family and friends every comfort. It's all about connectivity. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport's soaring success added 30 flights in 2024 and 2025, significant passenger growth, a new $72M runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. This home in the Atrium neighborhood of the master-planned community of Bay Isles could be your destination of choice. Features include a spectacular pool and spa, kayak launch, outdoor grills, and lush tropical landscaping. There is a shell path for walking along the bay and a sidewalk leading directly to the Town Center. The Bay Isles Beach Club is yours to enjoy the sand and world-class sunsets. There is also on-site management and maintenance staff making where home and away share the same address. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide's list of Top 12 Destinations for 2025.

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

It's all about location. Close to everything. Away from it all. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This single-story traditional condominium makes the most of its spaciously designed 2,105 square feet with open-plan living, three bedrooms, two full bathrooms, 30-foot balcony, and under-building parking and storage space. The bayside-inspired interior creates feelings of tranquility and hospitality throughout. The main living space enjoys abundant natural light and bay views from 9-foot sliding glass doors opening onto the balcony. The kitchen opens to the dining and living areas for effortless entertaining with added dining alfresco on the balcony. Wake up to views of the bay from the primary bedroom and just renovated en-suite bath offering peace in a soaking tub and spacious dual vanities. Completing the primary suite are separate spatial his and hers walk-in closets. Two guest wings, each with walk-in closets for added storage, extend family and friends every comfort. It's all about connectivity. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport's soaring success added 30 flights in 2024 and 2025, significant passenger growth, a new $72M runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. This home in the Atrium neighborhood of the master-planned community of Bay Isles could be your destination of choice. Features include a spectacular pool and spa, kayak launch, outdoor grills, and lush tropical landscaping. There is a shell path for walking along the bay and a sidewalk leading directly to the Town Center. The Bay Isles Beach Club is yours to enjoy the sand and world-class sunsets. There is also on-site management and maintenance staff making where home and away share the same address. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide's list of Top 12 Destinations for 2025.

2120 Harbourside Drive Unit 612, Longboat Key

$655,000

One or more photo(s) has been virtually staged. Island Living in Longbeach Village – 3 Bed, 3 Bath Coastal Retreat Discover the perfect blend of island charm and modern comfort in this beautifully updated 3-bedroom, 3-bathroom home nestled in the sought-after Longbeach Village of Longboat Key. Situated on a desirable corner lot, this residence offers the ultimate coastal lifestyle in one of the area’s most historic and beloved communities. Step inside to find a freshly remodeled main level, thoughtfully updated in 2025 with all-new appliances, cabinetry, and an energy-efficient HVAC system. Upstairs, the home’s highlight awaits—a spacious screened-in porch on the second level, ideal for morning coffee, evening cocktails, or simply soaking in the island breezes. From your doorstep, you’ll enjoy the convenience of being just a short stroll to renowned dining destinations like Mar Vista and Shore, as well as the powder-soft sands and turquoise waters of the Gulf of Mexico. Explore the boutiques and arts at St. Armands Circle to the south, or the shops and eateries of Anna Maria Island to the north—this home truly sits at the crossroads of it all. Embrace the rare Bay-to-Gulf lifestyle: wake up to spectacular sunrises along the bayfront and end your day with unforgettable sunsets over the Gulf. Whether as a full-time residence or a coastal getaway, this move-in-ready property is a rare opportunity to own a piece of paradise on Longboat Key.

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

One or more photo(s) has been virtually staged. Island Living in Longbeach Village – 3 Bed, 3 Bath Coastal Retreat Discover the perfect blend of island charm and modern comfort in this beautifully updated 3-bedroom, 3-bathroom home nestled in the sought-after Longbeach Village of Longboat Key. Situated on a desirable corner lot, this residence offers the ultimate coastal lifestyle in one of the area’s most historic and beloved communities. Step inside to find a freshly remodeled main level, thoughtfully updated in 2025 with all-new appliances, cabinetry, and an energy-efficient HVAC system. Upstairs, the home’s highlight awaits—a spacious screened-in porch on the second level, ideal for morning coffee, evening cocktails, or simply soaking in the island breezes. From your doorstep, you’ll enjoy the convenience of being just a short stroll to renowned dining destinations like Mar Vista and Shore, as well as the powder-soft sands and turquoise waters of the Gulf of Mexico. Explore the boutiques and arts at St. Armands Circle to the south, or the shops and eateries of Anna Maria Island to the north—this home truly sits at the crossroads of it all. Embrace the rare Bay-to-Gulf lifestyle: wake up to spectacular sunrises along the bayfront and end your day with unforgettable sunsets over the Gulf. Whether as a full-time residence or a coastal getaway, this move-in-ready property is a rare opportunity to own a piece of paradise on Longboat Key.

560 Cedar Street, Longboat Key

4825 Gulf Of Mexico Drive Unit 504, Longboat Key

$650,000

Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water. Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the scenery from multiple vantage points. Whether you’re looking for a full-time residence or a serene getaway, this condo delivers both comfort and location. The community is elevating its appeal with exciting enhancements, including upcoming clubhouse renovations featuring a boutique fitness center, newly refreshed landscaping, and a hot tub addition to the pool deck—creating a true resort-style atmosphere with two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan FURNISHED 5th floor panoramic view, master en-suite unit awaits YOU! Enjoy the best of island living with pristine beaches, nearby dining, and a relaxed yet refined lifestyle—all just moments from your door. R&R IS THE PACE, LBK IS THE PLACE!!!!

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

Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water. Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the scenery from multiple vantage points. Whether you’re looking for a full-time residence or a serene getaway, this condo delivers both comfort and location. The community is elevating its appeal with exciting enhancements, including upcoming clubhouse renovations featuring a boutique fitness center, newly refreshed landscaping, and a hot tub addition to the pool deck—creating a true resort-style atmosphere with two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan FURNISHED 5th floor panoramic view, master en-suite unit awaits YOU! Enjoy the best of island living with pristine beaches, nearby dining, and a relaxed yet refined lifestyle—all just moments from your door. R&R IS THE PACE, LBK IS THE PLACE!!!!

4825 Gulf Of Mexico Drive Unit 504, Longboat Key

4500 Gulf Of Mexico Dr Unit 305, Longboat Key

$650,000

Experience breathtaking Sarasota Bay views from every room in this beautifully customized Windward Bay condominium. This coastal retreat offers a seamless blend of elegance and comfort, featuring designer upgrades and thoughtful touches throughout. The open-concept living area is centered around a stunning custom fireplace — a feature that adds warmth and character to the space. Walls of windows fill the home with natural light and frame serene, panoramic bay and marina views, where dolphins, manatees, and pelicans glide across the water. The modern kitchen is equipped with stainless steel appliances and stylish finishes, while the spacious primary suite includes a generous walk-in closet and dressing area. Step onto the enclosed lanai, tiled underfoot, and savor peaceful mornings watching the sunrise over the bay. Every detail has been carefully curated — from updated flooring and custom woodwork to contemporart fixtures and generous storage throughout. Residents of pet friendly Windward Bay enjoy resort-style amenities including two heated pools, tennis and pickleball courts, fitness center, marinas with boat slips(fee and wait list), kayak storage, and deeded beach access just across the street. Perfectly located near Bayfront Park, shopping, dining, and St. Armands Circle, this home offers the best of Longboat Key living — tranquil, refined, and unmistakably coastal. Welcome home to the kind of life you don't just dream of-you live it here!

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

Experience breathtaking Sarasota Bay views from every room in this beautifully customized Windward Bay condominium. This coastal retreat offers a seamless blend of elegance and comfort, featuring designer upgrades and thoughtful touches throughout. The open-concept living area is centered around a stunning custom fireplace — a feature that adds warmth and character to the space. Walls of windows fill the home with natural light and frame serene, panoramic bay and marina views, where dolphins, manatees, and pelicans glide across the water. The modern kitchen is equipped with stainless steel appliances and stylish finishes, while the spacious primary suite includes a generous walk-in closet and dressing area. Step onto the enclosed lanai, tiled underfoot, and savor peaceful mornings watching the sunrise over the bay. Every detail has been carefully curated — from updated flooring and custom woodwork to contemporart fixtures and generous storage throughout. Residents of pet friendly Windward Bay enjoy resort-style amenities including two heated pools, tennis and pickleball courts, fitness center, marinas with boat slips(fee and wait list), kayak storage, and deeded beach access just across the street. Perfectly located near Bayfront Park, shopping, dining, and St. Armands Circle, this home offers the best of Longboat Key living — tranquil, refined, and unmistakably coastal. Welcome home to the kind of life you don't just dream of-you live it here!

4500 Gulf Of Mexico Dr Unit 305, Longboat Key

2020 Harbourside Drive Unit 432, Longboat Key

$650,000

Experience true elegance in this alluring 2-bedroom, 2-bathroom residence with breathtaking water views. Designed with the highest level of sophistication in mind, this inviting unit exceeds expectations, offering custom features throughout. The color palette, material selections, and design choices evoke the sophistication of a city skyscraper and the calming tranquility of a luxury hotel. Step inside to find sleek porcelain tile flooring, solid walnut and rift oak cabinetry, and double-thick stone countertops, all meticulously selected for a refined modern aesthetic. All new LED lighting throughout the home makes the art-filled space feel like a chic gallery. Expansive new hurricane-rated windows not only showcase the stunning waterfront vistas but also provide enhanced energy efficiency and storm protection. For added peace of mind, remote-controlled hurricane shutters have been installed over the impact-rated windows to ensure the residence remains protected no matter the weather. Nestled on the shoreline of Bay Isles, a gated community with 24-hour security, residents enjoy resort-style amenities, including a heated community pool, hot tub, fitness center, and elevator access. Golf enthusiasts will appreciate proximity to world-class golf courses (requiring membership) at the renowned Longboat Key Club. With private Bay Isles beach access, residents can step directly onto the pristine sands of Longboat Key. This prime location is also just steps from the brand-new St. Regis Hotel, offering fine dining, spa services, and exclusive luxury experiences. Additionally, the vibrant shopping and dining scene of St. Armands Circle is just a short drive away, providing an array of boutiques, cafés, and gourmet restaurants. This artful, curated residence is ready for you to move right in, with select art and furniture separately available.

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

Experience true elegance in this alluring 2-bedroom, 2-bathroom residence with breathtaking water views. Designed with the highest level of sophistication in mind, this inviting unit exceeds expectations, offering custom features throughout. The color palette, material selections, and design choices evoke the sophistication of a city skyscraper and the calming tranquility of a luxury hotel. Step inside to find sleek porcelain tile flooring, solid walnut and rift oak cabinetry, and double-thick stone countertops, all meticulously selected for a refined modern aesthetic. All new LED lighting throughout the home makes the art-filled space feel like a chic gallery. Expansive new hurricane-rated windows not only showcase the stunning waterfront vistas but also provide enhanced energy efficiency and storm protection. For added peace of mind, remote-controlled hurricane shutters have been installed over the impact-rated windows to ensure the residence remains protected no matter the weather. Nestled on the shoreline of Bay Isles, a gated community with 24-hour security, residents enjoy resort-style amenities, including a heated community pool, hot tub, fitness center, and elevator access. Golf enthusiasts will appreciate proximity to world-class golf courses (requiring membership) at the renowned Longboat Key Club. With private Bay Isles beach access, residents can step directly onto the pristine sands of Longboat Key. This prime location is also just steps from the brand-new St. Regis Hotel, offering fine dining, spa services, and exclusive luxury experiences. Additionally, the vibrant shopping and dining scene of St. Armands Circle is just a short drive away, providing an array of boutiques, cafés, and gourmet restaurants. This artful, curated residence is ready for you to move right in, with select art and furniture separately available.

2020 Harbourside Drive Unit 432, Longboat Key

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