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4500 Gulf Of Mexico Dr Unit 305, Longboat Key

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

4500 Gulf Of Mexico Drive Unit 202, Longboat Key

$650,000

UNDER CONTRACT. ACCEPTING BACKUP OFFERS.Wake up to shimmering Bay views and peaceful marina life in this updated, turnkey furnished, 2-bed, 2-bath Longboat Key retreat on 26 bayfront acres, with half a mile of walking trails along the Bay. This 1,312 sq ft residence features an open coastal layout, a bright remodeled kitchen with quartz countertops, and an oversized living area designed to frame the waterfront views. Step into the lanai and look out over the marina, mangroves, and wildlife — a tranquil backdrop that changes with the tides. The building’s rare pet policy allowing two pets, combined with its waterfront lifestyle, makes this one of the most desirable opportunities on Longboat Key. Enjoy beach access, 2 heated pools, 6 pickleball courts and tennis courts, kayak storage, bike storage, walking trails, fitness amenities, firepits, barbecue grills, picnic tables, 2 marinas, fishing piers, shuffleboard, clubhouse with a kitchen, library, fitness room, meeting room, 2 saunas, and walkability to restaurants. Whether you’re seeking a seasonal escape or a full-time coastal home, #202 delivers a relaxed, elevated lifestyle with a view you’ll never forget.

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

UNDER CONTRACT. ACCEPTING BACKUP OFFERS.Wake up to shimmering Bay views and peaceful marina life in this updated, turnkey furnished, 2-bed, 2-bath Longboat Key retreat on 26 bayfront acres, with half a mile of walking trails along the Bay. This 1,312 sq ft residence features an open coastal layout, a bright remodeled kitchen with quartz countertops, and an oversized living area designed to frame the waterfront views. Step into the lanai and look out over the marina, mangroves, and wildlife — a tranquil backdrop that changes with the tides. The building’s rare pet policy allowing two pets, combined with its waterfront lifestyle, makes this one of the most desirable opportunities on Longboat Key. Enjoy beach access, 2 heated pools, 6 pickleball courts and tennis courts, kayak storage, bike storage, walking trails, fitness amenities, firepits, barbecue grills, picnic tables, 2 marinas, fishing piers, shuffleboard, clubhouse with a kitchen, library, fitness room, meeting room, 2 saunas, and walkability to restaurants. Whether you’re seeking a seasonal escape or a full-time coastal home, #202 delivers a relaxed, elevated lifestyle with a view you’ll never forget.

4500 Gulf Of Mexico Drive Unit 202, Longboat Key

$645,000

Mid Key on Longboat Key, 825 Bayport Way offers 1,601 square feet of living with 2 bedrooms and 2 bathrooms in an active bayfront community. A great room design with split bedrooms. The Florida room with access to the private outdoor terrace has tremendous views...especially for a nature lover. Unit is being offered turnkey furnished… also can be sold unfurnished. Enjoy beautiful bay views and the ultimate Florida lifestyle with the beach just steps away, easy access to Longboat Key’s soft white sands and stunning Gulf sunsets. The residence is designed for comfort and ease, ideal as a full-time home or a serene coastal retreat. The Bayport community enhances the experience with a heated swimming pool, tennis courts, pickleball courts, bocce ball, kayak storage, deeded beach access with umbrellas and chairs, and even scenic walking paths that wind through lush, well-maintained grounds. Whether you’re paddling on the bay, strolling by the water, or enjoying quiet mornings at home watching the sunrise, this property captures the essence of island Located in the heart of Longboat Key. This bayfront condo offers an exceptional opportunity to enjoy the best of Florida’s Gulf Coast lifestyle. Just moments from dining and cultural attractions of Longboat Key and nearby Sarasota, the location blends privacy with convenience. The residence invites relaxed coastal living, whether you’re entertaining guests, enjoying peaceful mornings, or embracing an active outdoor lifestyle. This is a rare chance to own in one of Longboat Key’s most desirable areas, where timeless architecture meets everyday life.

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

Mid Key on Longboat Key, 825 Bayport Way offers 1,601 square feet of living with 2 bedrooms and 2 bathrooms in an active bayfront community. A great room design with split bedrooms. The Florida room with access to the private outdoor terrace has tremendous views...especially for a nature lover. Unit is being offered turnkey furnished… also can be sold unfurnished. Enjoy beautiful bay views and the ultimate Florida lifestyle with the beach just steps away, easy access to Longboat Key’s soft white sands and stunning Gulf sunsets. The residence is designed for comfort and ease, ideal as a full-time home or a serene coastal retreat. The Bayport community enhances the experience with a heated swimming pool, tennis courts, pickleball courts, bocce ball, kayak storage, deeded beach access with umbrellas and chairs, and even scenic walking paths that wind through lush, well-maintained grounds. Whether you’re paddling on the bay, strolling by the water, or enjoying quiet mornings at home watching the sunrise, this property captures the essence of island Located in the heart of Longboat Key. This bayfront condo offers an exceptional opportunity to enjoy the best of Florida’s Gulf Coast lifestyle. Just moments from dining and cultural attractions of Longboat Key and nearby Sarasota, the location blends privacy with convenience. The residence invites relaxed coastal living, whether you’re entertaining guests, enjoying peaceful mornings, or embracing an active outdoor lifestyle. This is a rare chance to own in one of Longboat Key’s most desirable areas, where timeless architecture meets everyday life.

825 Bayport Way Unit 825, Longboat Key

4960 Gulf Of Mexico Drive Unit 206, Longboat Key

$644,950

Public showings are now available for the first time. After months of restricted access due to a tenant, this residence is finally available for public showings. Restricted access resulted in only a handful of private showings, giving today’s buyers a rare chance to discover a home that’s been under the radar. Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. 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, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.

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

Public showings are now available for the first time. After months of restricted access due to a tenant, this residence is finally available for public showings. Restricted access resulted in only a handful of private showings, giving today’s buyers a rare chance to discover a home that’s been under the radar. Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. 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, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.

4960 Gulf Of Mexico Drive Unit 206, Longboat Key

1916 Harbourside Drive Unit 803, Longboat Key

$642,000

WOW, REDUCED PRICE AND MOTIVATED SELLER on this rarely available waterfront condominium in the coveted and gated Fairway Bay enclave of Bay Isles on Longboat Key, with beautiful unobstructed Bay, Channel, and Downtown Sarasota vistas, effortless access to the Bay from your deeded 40' boat dock (which can be rented out), and beach access at the private Bay Isles Beach Club. You can have it all in this spacious townhome with 2 bedrooms, 2.5 baths plus large bonus room! Featuring an open and bright ambiance which unfolds as you enter the front door to find a soaring 2-story ceiling, multiple skylights, and a neutral coastal tone. The main living space is centered around unobstructed water views, a marble-surround fireplace, large living room, dining room that is currently used as a sitting area, and seamless flow to the lovely light-filled lanai overlooking the tranquil channel and your private dock just steps away. The updated kitchen blends style and function with granite counters and backsplash, stainless appliances, glass-front illuminated cabinetry, a pantry, and a cheerful dining area framed by large windows. Upstairs, the flexible floor plan provides 2 private suites with ensuite baths which are both ideal for a primary or guest suite. The current primary suite features a large bedroom, walk-in closet, and an updated ensuite bath with glass surround shower and granite countertop. The split plan provides ideal privacy for the guest suite/office which boasts a wide picture window capturing the shimmering waterway, a generous walk-in closet, a bright bath with skylight, dual sinks, bathtub and tiled finishes. A versatile lower level includes a spacious air-conditioned bonus room for storage, a home gym or workshop, and parking for 2 cars, with a Garrison flood-protection system for extra peace of mind. Recent updates include new interior paint. Residents of Fairway Bay enjoy a refined resort lifestyle with 24-hour gated security, 2 heated pools, tennis and pickleball courts, a fitness center, a clubhouse for social gatherings, on-site management, and generous guest parking. As part of Bay Isles, owners also have deeded access to the private Bay Isles Beach Club on the Gulf of Mexico plus optional membership to the Longboat Key Club. Enjoy morning breezes over the water, dazzling sunsets, canopied walking trails, and the freedom to explore Sarasota Bay directly from your dock define an unmatched blend of serenity and coastal recreation. Life on Longboat Key offers effortless access to St. Armands Circle, Lido Beach, downtown Sarasota, and Anna Maria Island, creating the perfect balance between island tranquility and sophisticated coastal living.

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

WOW, REDUCED PRICE AND MOTIVATED SELLER on this rarely available waterfront condominium in the coveted and gated Fairway Bay enclave of Bay Isles on Longboat Key, with beautiful unobstructed Bay, Channel, and Downtown Sarasota vistas, effortless access to the Bay from your deeded 40' boat dock (which can be rented out), and beach access at the private Bay Isles Beach Club. You can have it all in this spacious townhome with 2 bedrooms, 2.5 baths plus large bonus room! Featuring an open and bright ambiance which unfolds as you enter the front door to find a soaring 2-story ceiling, multiple skylights, and a neutral coastal tone. The main living space is centered around unobstructed water views, a marble-surround fireplace, large living room, dining room that is currently used as a sitting area, and seamless flow to the lovely light-filled lanai overlooking the tranquil channel and your private dock just steps away. The updated kitchen blends style and function with granite counters and backsplash, stainless appliances, glass-front illuminated cabinetry, a pantry, and a cheerful dining area framed by large windows. Upstairs, the flexible floor plan provides 2 private suites with ensuite baths which are both ideal for a primary or guest suite. The current primary suite features a large bedroom, walk-in closet, and an updated ensuite bath with glass surround shower and granite countertop. The split plan provides ideal privacy for the guest suite/office which boasts a wide picture window capturing the shimmering waterway, a generous walk-in closet, a bright bath with skylight, dual sinks, bathtub and tiled finishes. A versatile lower level includes a spacious air-conditioned bonus room for storage, a home gym or workshop, and parking for 2 cars, with a Garrison flood-protection system for extra peace of mind. Recent updates include new interior paint. Residents of Fairway Bay enjoy a refined resort lifestyle with 24-hour gated security, 2 heated pools, tennis and pickleball courts, a fitness center, a clubhouse for social gatherings, on-site management, and generous guest parking. As part of Bay Isles, owners also have deeded access to the private Bay Isles Beach Club on the Gulf of Mexico plus optional membership to the Longboat Key Club. Enjoy morning breezes over the water, dazzling sunsets, canopied walking trails, and the freedom to explore Sarasota Bay directly from your dock define an unmatched blend of serenity and coastal recreation. Life on Longboat Key offers effortless access to St. Armands Circle, Lido Beach, downtown Sarasota, and Anna Maria Island, creating the perfect balance between island tranquility and sophisticated coastal living.

1916 Harbourside Drive Unit 803, Longboat Key

2089 Gulf Of Mexico Drive Unit G1-108, Longboat Key

$635,000

Welcome to G1-108, a recently remodeled and fully-furnished residence in Seaplace! Overlooking the pristine sands and sunsets of the Gulf, this first-floor 2 bedroom/2 bathroom residence offers unparalleled access to the beach and resort-style amenities. In early 2025, this residence was extensively remodeled, including impact-resistant hurricane door, new bathrooms and a new kitchen with stainless steel appliances and modern cabinetry. The master suite is a cozy, spacious retreat with a walk-in closet and bathroom. The second bedroom is the perfect space for family and guests, featuring 2 twin beds and a full bathroom. The home also features a new lanai, a comfortable place to relax and soak in the views. Sliding door and all windows are hurricane impact rated. Complimentary with the residence is one parking spot and a designated storage space - perfect for storing any extra beach gear. This residence is being offered furnished. Seaplace is a premier, 24-hour gated and guarded community on Longboat Key. The community boasts 2 swimming pools and hot tubs, a clubhouse and fitness center, fire pit, playground, grilling station, outdoor showers and three Har-Tru tennis courts. Perhaps the most stand-out amenity of this community is its direct beach access already set with lounge chairs and umbrellas. All you have to bring is yourself, your sunscreen and your towel! Going to the beach could not get any easier. Just a short distance from grocery shopping, local boutiques and first-class restaurants and entertainment, G1-108 is perfectly situated to give you that beachfront lifestyle you’ve been looking for. Everything that Longboat Key, St. Armand’s Circle, Anna Maria Island and Downtown Sarasota have in store is at your fingertips. Whether as your primary residence, second home or investment opportunity, G1-108 cannot be missed!

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

Welcome to G1-108, a recently remodeled and fully-furnished residence in Seaplace! Overlooking the pristine sands and sunsets of the Gulf, this first-floor 2 bedroom/2 bathroom residence offers unparalleled access to the beach and resort-style amenities. In early 2025, this residence was extensively remodeled, including impact-resistant hurricane door, new bathrooms and a new kitchen with stainless steel appliances and modern cabinetry. The master suite is a cozy, spacious retreat with a walk-in closet and bathroom. The second bedroom is the perfect space for family and guests, featuring 2 twin beds and a full bathroom. The home also features a new lanai, a comfortable place to relax and soak in the views. Sliding door and all windows are hurricane impact rated. Complimentary with the residence is one parking spot and a designated storage space - perfect for storing any extra beach gear. This residence is being offered furnished. Seaplace is a premier, 24-hour gated and guarded community on Longboat Key. The community boasts 2 swimming pools and hot tubs, a clubhouse and fitness center, fire pit, playground, grilling station, outdoor showers and three Har-Tru tennis courts. Perhaps the most stand-out amenity of this community is its direct beach access already set with lounge chairs and umbrellas. All you have to bring is yourself, your sunscreen and your towel! Going to the beach could not get any easier. Just a short distance from grocery shopping, local boutiques and first-class restaurants and entertainment, G1-108 is perfectly situated to give you that beachfront lifestyle you’ve been looking for. Everything that Longboat Key, St. Armand’s Circle, Anna Maria Island and Downtown Sarasota have in store is at your fingertips. Whether as your primary residence, second home or investment opportunity, G1-108 cannot be missed!

2089 Gulf Of Mexico Drive Unit G1-108, Longboat Key

1928 Harbourside Drive Unit 1403, Longboat Key

$635,000

REDUCED PRICE! Are you looking for a RESORT home with spacious rooms, fine finishes, vaulted ceilings and the convenience of a condo community with bay and beach access? Look no further. Luxury and style await in this beautifully updated townhouse, located behind the gates of the exclusive Bay Isles resort. With 1,590 sq. ft. of meticulously designed and finished indoor living space plus another 1,100 sq. ft. of screened lanai, storage and garage space, this resort home provides the ultimate in luxe living, comfort and convenience. Upon entering this home, you're greeted by an open concept great room and designer kitchen, vaulted ceilings, a conveniently placed guest bathroom, and views over the very private community pool. You'll never want to leave! The gourmet kitchen is a chef’s dream, featuring gleaming granite countertops including a striking azure blue granite breakfast bar, custom mosaic glass tile backsplash, solid wood cabinetry, and stainless JennAir appliances. Easy to maintain luxury vinyl plank floors flow throughout, adding sophistication and durability. Soaring cathedral ceilings and abundant natural light enhance the light, bright, spacious feel of this home and the private screened lanai offers a serene retreat with access to lushly landscaped grounds and the resort style pool. The oversized primary suite boasts vaulted ceilings, a walk-in closet, and an elegant ensuite bath with natural stone and custom tile shower. The second bedroom also has a vaulted ceiling plus walk-in closet and beautifully finished adjacent bathroom. The ground-level garage has extra depth enabling covered parking for two cars plus there's a separate room that can be flexibly used for storage, a home gym, or a wine cellar. As a Bay Isles resident, you'll enjoy exclusive access to resident-only amenities including a private clubhouse, fitness center, heated pool and spa, tennis courts, and the private Bay Isles Beach Club. This resort home is just minutes from the vibrant dining, shopping, and cultural scene of St. Armands Circle and downtown Sarasota. See this home today and enjoy the best of Longboat Key living.

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

REDUCED PRICE! Are you looking for a RESORT home with spacious rooms, fine finishes, vaulted ceilings and the convenience of a condo community with bay and beach access? Look no further. Luxury and style await in this beautifully updated townhouse, located behind the gates of the exclusive Bay Isles resort. With 1,590 sq. ft. of meticulously designed and finished indoor living space plus another 1,100 sq. ft. of screened lanai, storage and garage space, this resort home provides the ultimate in luxe living, comfort and convenience. Upon entering this home, you're greeted by an open concept great room and designer kitchen, vaulted ceilings, a conveniently placed guest bathroom, and views over the very private community pool. You'll never want to leave! The gourmet kitchen is a chef’s dream, featuring gleaming granite countertops including a striking azure blue granite breakfast bar, custom mosaic glass tile backsplash, solid wood cabinetry, and stainless JennAir appliances. Easy to maintain luxury vinyl plank floors flow throughout, adding sophistication and durability. Soaring cathedral ceilings and abundant natural light enhance the light, bright, spacious feel of this home and the private screened lanai offers a serene retreat with access to lushly landscaped grounds and the resort style pool. The oversized primary suite boasts vaulted ceilings, a walk-in closet, and an elegant ensuite bath with natural stone and custom tile shower. The second bedroom also has a vaulted ceiling plus walk-in closet and beautifully finished adjacent bathroom. The ground-level garage has extra depth enabling covered parking for two cars plus there's a separate room that can be flexibly used for storage, a home gym, or a wine cellar. As a Bay Isles resident, you'll enjoy exclusive access to resident-only amenities including a private clubhouse, fitness center, heated pool and spa, tennis courts, and the private Bay Isles Beach Club. This resort home is just minutes from the vibrant dining, shopping, and cultural scene of St. Armands Circle and downtown Sarasota. See this home today and enjoy the best of Longboat Key living.

1928 Harbourside Drive Unit 1403, Longboat Key

2000 Harbourside Drive Unit 1501, Longboat Key

$630,000

Nestled in the attractive community of Fairway Bay in Bay Isles on Longboat Key is this fabulous 2BR/2BA elevated townhouse. This tastefully decorated condo residence is on one level above the oversized 2-car garage and is an end unit. It is beautifully maintained, in great condition and offered turnkey-furnished with upscale furnishing from Robb & Stucky. The spacious living room and dining room has high ceilings, crown molding, plantation shutters, a fireplace and a wet bar with built-ins. The updated kitchen completed in 2025 is a neutral palette with new white cabinetry, white quartz countertops, a super pull-out pantry, all new appliances and washer & dryer in the past 12 months. A/C replaced in 2020 & water heater in 2021. The flooring in the entire residence was recently replaced with luxury vinyl plank flooring. A spacious shaded screened lanai offers a peaceful garden view and is a short walk to the heated pool and the bay. The bathrooms have also been updated in 2025 with new flooring, new cabinets, fixtures and shower door. The primary bedroom suite is a quiet sanctuary offering ample room for your apparel with two walk-in closets and Hunter-Douglas window blinds. This townhouse affords plenty of room for guests and a large family to stay and feels like a single-family home. There is a two-and-a-half garage with a large finished air-conditioned space on the ground floor giving you extra space. Community amenities include walking paths, 2 heated pools, a fitness room, tennis & pickle ball courts and a social room. The building will soon benefit from a new roof, which the seller has paid for. Residents benefit from on-site management and 24-hour security. Ownership includes deeded access to the private Bay Isles Beach Club, featuring a Gulf front pavilion, grilling areas, and beautiful sandy beaches. Located within the Longboat Key Club, residents have the option to join golf, tennis, and social memberships, all just minutes from the boutiques and dining on world-renowned St. Armands Circle, downtown Sarasota’s cultural attractions and Harbourside Marina.

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

Nestled in the attractive community of Fairway Bay in Bay Isles on Longboat Key is this fabulous 2BR/2BA elevated townhouse. This tastefully decorated condo residence is on one level above the oversized 2-car garage and is an end unit. It is beautifully maintained, in great condition and offered turnkey-furnished with upscale furnishing from Robb & Stucky. The spacious living room and dining room has high ceilings, crown molding, plantation shutters, a fireplace and a wet bar with built-ins. The updated kitchen completed in 2025 is a neutral palette with new white cabinetry, white quartz countertops, a super pull-out pantry, all new appliances and washer & dryer in the past 12 months. A/C replaced in 2020 & water heater in 2021. The flooring in the entire residence was recently replaced with luxury vinyl plank flooring. A spacious shaded screened lanai offers a peaceful garden view and is a short walk to the heated pool and the bay. The bathrooms have also been updated in 2025 with new flooring, new cabinets, fixtures and shower door. The primary bedroom suite is a quiet sanctuary offering ample room for your apparel with two walk-in closets and Hunter-Douglas window blinds. This townhouse affords plenty of room for guests and a large family to stay and feels like a single-family home. There is a two-and-a-half garage with a large finished air-conditioned space on the ground floor giving you extra space. Community amenities include walking paths, 2 heated pools, a fitness room, tennis & pickle ball courts and a social room. The building will soon benefit from a new roof, which the seller has paid for. Residents benefit from on-site management and 24-hour security. Ownership includes deeded access to the private Bay Isles Beach Club, featuring a Gulf front pavilion, grilling areas, and beautiful sandy beaches. Located within the Longboat Key Club, residents have the option to join golf, tennis, and social memberships, all just minutes from the boutiques and dining on world-renowned St. Armands Circle, downtown Sarasota’s cultural attractions and Harbourside Marina.

2000 Harbourside Drive Unit 1501, Longboat Key

3070 Grand Bay Boulevard Unit 612, Longboat Key

$629,950

LOWEST PRICED 2 BEDROOM CONDO IN BAY ISLES. This desirable corner residence at Grand Bay showcases an expansive wraparound terrace overlooking Sarasota Bay—perfect for enjoying stunning sunrises over the Bay and sunsets over the gardens and golf course. Uniquely positioned for privacy, this home has been tastefully updated with a neutral color palette and comes fully furnished, and is the lowest-priced 2 Bedroom condo in prestigious Bay Isles. The kitchen shines with quartz countertops, full-height backsplash, double oven, new sink and plumbing fixtures, under-cabinet lighting, and stainless appliances. A convenient pass-through connects seamlessly to the living area for easy entertaining. The primary suite offers floor-to-ceiling sliders opening to the oversized terrace, a luxurious ensuite bath with double vanity, glass-enclosed shower, jetted soaking tub, and custom walk-in closet. The private guest suite features its own bath, large walk-in closet, terrace access, and pocket doors for added privacy. Both Bedrooms have wide plank hardwood floors. Additional highlights include two side-by-side under-building parking spaces near the elevator, and a private storage locker. Grand Bay is a pet-friendly, guard-gated community offering resort-style living with semi-private elevators, a state-of-the-art fitness center, Har-Tru tennis courts, outdoor grills, and two sparkling pools. Residents also enjoy membership in the private Bay Isles Beach Club with deeded beach access, pavilion, restrooms, and gated parking.

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

LOWEST PRICED 2 BEDROOM CONDO IN BAY ISLES. This desirable corner residence at Grand Bay showcases an expansive wraparound terrace overlooking Sarasota Bay—perfect for enjoying stunning sunrises over the Bay and sunsets over the gardens and golf course. Uniquely positioned for privacy, this home has been tastefully updated with a neutral color palette and comes fully furnished, and is the lowest-priced 2 Bedroom condo in prestigious Bay Isles. The kitchen shines with quartz countertops, full-height backsplash, double oven, new sink and plumbing fixtures, under-cabinet lighting, and stainless appliances. A convenient pass-through connects seamlessly to the living area for easy entertaining. The primary suite offers floor-to-ceiling sliders opening to the oversized terrace, a luxurious ensuite bath with double vanity, glass-enclosed shower, jetted soaking tub, and custom walk-in closet. The private guest suite features its own bath, large walk-in closet, terrace access, and pocket doors for added privacy. Both Bedrooms have wide plank hardwood floors. Additional highlights include two side-by-side under-building parking spaces near the elevator, and a private storage locker. Grand Bay is a pet-friendly, guard-gated community offering resort-style living with semi-private elevators, a state-of-the-art fitness center, Har-Tru tennis courts, outdoor grills, and two sparkling pools. Residents also enjoy membership in the private Bay Isles Beach Club with deeded beach access, pavilion, restrooms, and gated parking.

3070 Grand Bay Boulevard Unit 612, Longboat Key

5757 Gulf Of Mexico Drive Unit 115, Longboat Key

$625,000

Lush garden views and a peek at the Gulf are enjoyed from this 2 bedroom 1st floor walkout residence at The Shore. Owners will appreciate the well positioned primary suite with separate access to the terrace, a walk-in closet and gulf water views. The spacious kitchen offers abundant counter space, an exterior door and a desk area that could also be used as a breakfast nook. Guests will relax in comfort with their own full bath, plantation shutters and plenty of space to unwind. Other highlights include a storage space, an assigned covered parking space and a separate laundry room. The intimate pet friendly community of The Shore offers excellent amenities with a gulf front heated pool and spa, sauna, fitness room with weights, a sundeck terrace, a large social room with full kitchen, bike storage and beautifully landscaped expansive grounds. With 500 feet of water frontage and miles of beach to explore, there is much to be thankful for at The Shore. Conveniently located close to shopping, fine and casual dining, the post office, Publix, St. Armands and downtown Sarasota.

2 Beds ⋅ 2 Baths ⋅ Shore Condominium The SubDv. ⋅ 34228 Zip Code

Lush garden views and a peek at the Gulf are enjoyed from this 2 bedroom 1st floor walkout residence at The Shore. Owners will appreciate the well positioned primary suite with separate access to the terrace, a walk-in closet and gulf water views. The spacious kitchen offers abundant counter space, an exterior door and a desk area that could also be used as a breakfast nook. Guests will relax in comfort with their own full bath, plantation shutters and plenty of space to unwind. Other highlights include a storage space, an assigned covered parking space and a separate laundry room. The intimate pet friendly community of The Shore offers excellent amenities with a gulf front heated pool and spa, sauna, fitness room with weights, a sundeck terrace, a large social room with full kitchen, bike storage and beautifully landscaped expansive grounds. With 500 feet of water frontage and miles of beach to explore, there is much to be thankful for at The Shore. Conveniently located close to shopping, fine and casual dining, the post office, Publix, St. Armands and downtown Sarasota.

5757 Gulf Of Mexico Drive Unit 115, Longboat Key

4835 Gulf Of Mexico Drive Unit 105, Longboat Key

$625,000

Experience direct Gulf-front living in this furnished, first-floor walkout residence at The Westchester on Longboat Key. Enjoy sweeping turquoise water views from nearly every room, with miles of pristine shoreline just beyond your door. This well-appointed, inviting two-bedroom, two-bath condominium features a spacious split floor plan designed for comfort and privacy, along with seamless indoor-outdoor living and immediate access to the pool and beach. The kitchen is equipped with stainless steel appliances, solid surface countertops, and abundant cabinetry and prep space. Both bedrooms offer en suite baths and generous walk-in closets, complemented by additional storage. The primary suite features a private screened lanai overlooking the Gulf, creating a tranquil retreat. A second expansive screened lanai off the great room captures panoramic water views and opens directly to the community pool and beach. An in-unit washer and dryer add everyday convenience. This thoughtfully designed, fully furnished residence is ideal for effortless coastal living, whether as a primary home, vacation getaway, or investment opportunity. The unit includes assigned covered parking and private storage conveniently just outside the entry. Community amenities include lighted tennis and pickleball courts, a basketball court, two heated pools, shuffleboard, outdoor grilling areas with cabanas, kayak and bicycle storage, and private beach gear lockers. A newly renovated clubhouse is coming soon and will feature 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 provides convenient access to Bayfront Park with its dog parks and waterfront views, as well as nearby shopping and daily conveniences, including Publix. Residents are minutes from the Centre Shops and Whitney Plaza, along with more than a dozen popular north-end restaurants, including waterfront favorites such as Shore Restaurant and Mar Vista Dockside Restaurant. Longboat Key also offers a private golf course, a full-service marina, and multiple waterfront parks. Nearby destinations include St. Armands Circle and downtown Sarasota, renowned for its vibrant arts and cultural scene.

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

Experience direct Gulf-front living in this furnished, first-floor walkout residence at The Westchester on Longboat Key. Enjoy sweeping turquoise water views from nearly every room, with miles of pristine shoreline just beyond your door. This well-appointed, inviting two-bedroom, two-bath condominium features a spacious split floor plan designed for comfort and privacy, along with seamless indoor-outdoor living and immediate access to the pool and beach. The kitchen is equipped with stainless steel appliances, solid surface countertops, and abundant cabinetry and prep space. Both bedrooms offer en suite baths and generous walk-in closets, complemented by additional storage. The primary suite features a private screened lanai overlooking the Gulf, creating a tranquil retreat. A second expansive screened lanai off the great room captures panoramic water views and opens directly to the community pool and beach. An in-unit washer and dryer add everyday convenience. This thoughtfully designed, fully furnished residence is ideal for effortless coastal living, whether as a primary home, vacation getaway, or investment opportunity. The unit includes assigned covered parking and private storage conveniently just outside the entry. Community amenities include lighted tennis and pickleball courts, a basketball court, two heated pools, shuffleboard, outdoor grilling areas with cabanas, kayak and bicycle storage, and private beach gear lockers. A newly renovated clubhouse is coming soon and will feature 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 provides convenient access to Bayfront Park with its dog parks and waterfront views, as well as nearby shopping and daily conveniences, including Publix. Residents are minutes from the Centre Shops and Whitney Plaza, along with more than a dozen popular north-end restaurants, including waterfront favorites such as Shore Restaurant and Mar Vista Dockside Restaurant. Longboat Key also offers a private golf course, a full-service marina, and multiple waterfront parks. Nearby destinations include St. Armands Circle and downtown Sarasota, renowned for its vibrant arts and cultural scene.

4835 Gulf Of Mexico Drive Unit 105, Longboat Key

$625,000

Outstanding opportunity in the historic Longboat Key Village of Longbeach. The existing 4BR/3BA/2,173sf home on this oversized 9,000 sq. ft. corner lot sustained storm damage and is ready for either a full renovation or a complete rebuild. Measuring 75x120 feet, the property sits in the peaceful southeastern corner of the village, surrounded by classic island charm and local favorites like Shore Restaurant, Mar Vista Dockside, and Whitney’s. Whitney Plaza is just moments away for additional dining and shopping options. Residents here also enjoy access to the community dock with water service, a fish cleaning station, and a boat ramp—perfect for boating and fishing enthusiasts. Ideal for builders, developers, or buyers ready to invest their vision and creativity into this prime coastal location.

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

Outstanding opportunity in the historic Longboat Key Village of Longbeach. The existing 4BR/3BA/2,173sf home on this oversized 9,000 sq. ft. corner lot sustained storm damage and is ready for either a full renovation or a complete rebuild. Measuring 75x120 feet, the property sits in the peaceful southeastern corner of the village, surrounded by classic island charm and local favorites like Shore Restaurant, Mar Vista Dockside, and Whitney’s. Whitney Plaza is just moments away for additional dining and shopping options. Residents here also enjoy access to the community dock with water service, a fish cleaning station, and a boat ramp—perfect for boating and fishing enthusiasts. Ideal for builders, developers, or buyers ready to invest their vision and creativity into this prime coastal location.

6901 Poinsetta Avenue, Longboat Key

225 Sands Point Road Unit 6201, Longboat Key

$625,000

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

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

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

225 Sands Point Road Unit 6201, Longboat Key

225 Sands Point Road Unit 7205, Longboat Key

$625,000

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

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

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

225 Sands Point Road Unit 7205, Longboat Key

4440 Exeter Drive Unit 206, Longboat Key

$625,000

Welcome to coastal living! This beautifully renovated, fully furnished 2BD/2BA end-unit condo on Longboat Key, offering stunning bay views and bright, beachy vibes throughout. This home is being sold fully furnished, making it effortless to settle in and start enjoying the island lifestyle right away. An inviting entryway leads into a uniquely redesigned open-concept kitchen, giving the unit a spacious, modern feel not found in other floor plans. Large windows fill the living space and both bedrooms with natural light and showcase gorgeous sunrise and sunset skies over the bay. Inside, you’ll find sleek tile flooring, updated appliances, a wine fridge, generous storage, and a private washer and dryer conveniently located in the primary bedroom closet. New sliders open to a roomy enclosed patio overlooking the canal—perfect for morning coffee, evening cocktails, or simply relaxing with the water views. This is also the only unit in the community featuring full hurricane-rated windows and automatic storm shutters, offering exceptional protection and comfort. An assigned covered parking space is included. Life at Longboat Harbour feels like joining a vibrant, active coastal community. Along with your own private storage locker and convenient bike/kayak storage, the neighborhood is ideal for anyone who loves the water. Deep-water canal access leads directly into Sarasota Bay, with boat slips available on a first-come basis and easy kayak launch areas for spontaneous paddle trips. The community is known for its friendly atmosphere and wide range of things to do. Enjoy pickleball, tennis, shuffleboard, mini-golf, and a full calendar of social clubs and events. The bayfront recreation room, with its water views, kitchen, and dance floor, is a favorite spot for social events and lively community gatherings. When it’s time to unwind, four heated pools provide plenty of spots to relax and soak up the sun. For beach days, residents have PRIVATE DEEDED BEACH access just across Gulf of Mexico Drive, complete with covered seating, restrooms, dressing areas, and convenient parking—making every trip to the sand effortless and enjoyable. Nestled in the heart of Longboat Key, the community sits between Anna Maria Island and St. Armands Circle, putting endless dining, shopping, and entertainment just minutes away. From waterfront restaurants and tiki bars to boutique shops and local cafés, the area offers plenty to explore. Longboat Key’s miles of pristine beaches, bike paths, and boater-friendly waterways make it a favorite for outdoor enthusiasts, whether you’re boating, paddling, fishing, beachcombing, or simply soaking up the island sunshine. Community roof replacements are underway, with this building scheduled for early 2026—assessment already PAID in full by seller. Freshly updated, fully furnished, and steps from resort-style amenities, this unit captures the comfort, charm, and laid-back vibe of Florida living. HIGHLY MOTIVATED SELLER and PRICED TO MOVE - this end unit gem won’t last long. Schedule a showing today!

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

Welcome to coastal living! This beautifully renovated, fully furnished 2BD/2BA end-unit condo on Longboat Key, offering stunning bay views and bright, beachy vibes throughout. This home is being sold fully furnished, making it effortless to settle in and start enjoying the island lifestyle right away. An inviting entryway leads into a uniquely redesigned open-concept kitchen, giving the unit a spacious, modern feel not found in other floor plans. Large windows fill the living space and both bedrooms with natural light and showcase gorgeous sunrise and sunset skies over the bay. Inside, you’ll find sleek tile flooring, updated appliances, a wine fridge, generous storage, and a private washer and dryer conveniently located in the primary bedroom closet. New sliders open to a roomy enclosed patio overlooking the canal—perfect for morning coffee, evening cocktails, or simply relaxing with the water views. This is also the only unit in the community featuring full hurricane-rated windows and automatic storm shutters, offering exceptional protection and comfort. An assigned covered parking space is included. Life at Longboat Harbour feels like joining a vibrant, active coastal community. Along with your own private storage locker and convenient bike/kayak storage, the neighborhood is ideal for anyone who loves the water. Deep-water canal access leads directly into Sarasota Bay, with boat slips available on a first-come basis and easy kayak launch areas for spontaneous paddle trips. The community is known for its friendly atmosphere and wide range of things to do. Enjoy pickleball, tennis, shuffleboard, mini-golf, and a full calendar of social clubs and events. The bayfront recreation room, with its water views, kitchen, and dance floor, is a favorite spot for social events and lively community gatherings. When it’s time to unwind, four heated pools provide plenty of spots to relax and soak up the sun. For beach days, residents have PRIVATE DEEDED BEACH access just across Gulf of Mexico Drive, complete with covered seating, restrooms, dressing areas, and convenient parking—making every trip to the sand effortless and enjoyable. Nestled in the heart of Longboat Key, the community sits between Anna Maria Island and St. Armands Circle, putting endless dining, shopping, and entertainment just minutes away. From waterfront restaurants and tiki bars to boutique shops and local cafés, the area offers plenty to explore. Longboat Key’s miles of pristine beaches, bike paths, and boater-friendly waterways make it a favorite for outdoor enthusiasts, whether you’re boating, paddling, fishing, beachcombing, or simply soaking up the island sunshine. Community roof replacements are underway, with this building scheduled for early 2026—assessment already PAID in full by seller. Freshly updated, fully furnished, and steps from resort-style amenities, this unit captures the comfort, charm, and laid-back vibe of Florida living. HIGHLY MOTIVATED SELLER and PRICED TO MOVE - this end unit gem won’t last long. Schedule a showing today!

4440 Exeter Drive Unit 206, Longboat Key

5055 Gulf Of Mexico Drive Unit 422, Longboat Key

$625,000

Luxury turnkey furnished beach condominium in the sought-after resort-style Club Longboat Beach and Tennis community. Near the beautiful sandy beaches on the Gulf, experience captivating sunsets from Longboat Key’s 10-mile sugary sandy beaches with your own private beach access. Imagine waking up to lush, pristine landscaping, tropical sea oats, and sparkling blue Gulf waters with the sound of crashing waves providing you with peace and serenity. This amazing community also offers the best tennis courts on the Island, with 8 Har-Tru Tennis courts, lights for night play, a dedicated tennis pro and a ball machine to allow you hours of practice to perfect your tennis game. This move-in ready fully furnished 1,624-square-foot two-bedroom, two bath unit provides an open kitchen, spacious living room with adjacent private balcony with partial water views, an integrated dining room, a bonus room and interior laundry room. Enjoy comfort and style accented with exquisite décor and custom furnishings, the home is outfitted with real wood floors, hurricane-impact windows, plantation shutter sliders, two living areas, one could be converted into a third bedroom or office, and two balconies of 140 square feet each of outside living area. The primary bedroom has an en-suite bath, king-size bed, dual custom built closets and a private balcony to enjoy your morning coffee. The guest bedroom you will find cozy with a double-size bed. The kitchen offers plenty of cabinet space, granite counters plus a wine cooler. This spotless home is well maintained, has tons of storage including an outdoor storage closet for your beach toys, covered parking for one car and plenty of parking for guests. On the second floor, the unit is accessible by elevator or stairs. Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, tennis, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat has 85 well-managed units and is a pet-friendly community allowing up to two pets. The condominium fees include exterior maintenance and insurance, cable, water, sewer and trash. Make it your home or a rental property. The minimum lease is one month and can be rented up to 12 times per year. Only a short drive to many fine restaurants, shops, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Make your appointment today to see this amazing home!

2 Beds ⋅ 2 Baths ⋅ Club Longboat Beach & Tennis SubDv. ⋅ 34228 Zip Code

Luxury turnkey furnished beach condominium in the sought-after resort-style Club Longboat Beach and Tennis community. Near the beautiful sandy beaches on the Gulf, experience captivating sunsets from Longboat Key’s 10-mile sugary sandy beaches with your own private beach access. Imagine waking up to lush, pristine landscaping, tropical sea oats, and sparkling blue Gulf waters with the sound of crashing waves providing you with peace and serenity. This amazing community also offers the best tennis courts on the Island, with 8 Har-Tru Tennis courts, lights for night play, a dedicated tennis pro and a ball machine to allow you hours of practice to perfect your tennis game. This move-in ready fully furnished 1,624-square-foot two-bedroom, two bath unit provides an open kitchen, spacious living room with adjacent private balcony with partial water views, an integrated dining room, a bonus room and interior laundry room. Enjoy comfort and style accented with exquisite décor and custom furnishings, the home is outfitted with real wood floors, hurricane-impact windows, plantation shutter sliders, two living areas, one could be converted into a third bedroom or office, and two balconies of 140 square feet each of outside living area. The primary bedroom has an en-suite bath, king-size bed, dual custom built closets and a private balcony to enjoy your morning coffee. The guest bedroom you will find cozy with a double-size bed. The kitchen offers plenty of cabinet space, granite counters plus a wine cooler. This spotless home is well maintained, has tons of storage including an outdoor storage closet for your beach toys, covered parking for one car and plenty of parking for guests. On the second floor, the unit is accessible by elevator or stairs. Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, tennis, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat has 85 well-managed units and is a pet-friendly community allowing up to two pets. The condominium fees include exterior maintenance and insurance, cable, water, sewer and trash. Make it your home or a rental property. The minimum lease is one month and can be rented up to 12 times per year. Only a short drive to many fine restaurants, shops, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Make your appointment today to see this amazing home!

5055 Gulf Of Mexico Drive Unit 422, Longboat Key

4621 Gulf Of Mexico Drive Unit 16B, Longboat Key

$625,000

Imagine the serene sands of the Gulf, just steps away, offering the ideal blend of luxury and opportunity with rental income while you're away. An on-site rental office ensures seamless bookings for your beautifully renovated condominium with new A/C at Casa Del Mar. You and your guests will relish the gulf-front pool, tennis courts with pickleball, grilling area and picnic tables, all while basking in the soothing embrace of the gulf waters as the simple, fulfilling life awaits. For those who wish to travel light, the unit is turnkey furnished, fully equipped, and ready to provide your ideal beach getaway. Upgrades include new kitchen and baths, quartz countertops and tile throughout, and stainless-steel appliances. The unit comes with a washer and dryer. just a short drive to local restaurants, Anna Maria Island, local parks, grocery shopping, CVS, places of worship, banks, world-renowned St, Armands Circle, top-rated Sarasota and all it offers.

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

Imagine the serene sands of the Gulf, just steps away, offering the ideal blend of luxury and opportunity with rental income while you're away. An on-site rental office ensures seamless bookings for your beautifully renovated condominium with new A/C at Casa Del Mar. You and your guests will relish the gulf-front pool, tennis courts with pickleball, grilling area and picnic tables, all while basking in the soothing embrace of the gulf waters as the simple, fulfilling life awaits. For those who wish to travel light, the unit is turnkey furnished, fully equipped, and ready to provide your ideal beach getaway. Upgrades include new kitchen and baths, quartz countertops and tile throughout, and stainless-steel appliances. The unit comes with a washer and dryer. just a short drive to local restaurants, Anna Maria Island, local parks, grocery shopping, CVS, places of worship, banks, world-renowned St, Armands Circle, top-rated Sarasota and all it offers.

4621 Gulf Of Mexico Drive Unit 16B, Longboat Key

450 Gulf Of Mexico Drive Unit B207, Longboat Key

$620,000

Where can you find an exquisite 3-bedroom waterfront condo on the coveted South End of Longboat Key under $700,000? Discover the ultimate island lifestyle in this beautifully furnished end unit located in the highly sought-after Bay Harbour community. Boasting a desired southern exposure, lower maintenance fees, and a pet-friendly policy, this condo is the perfect blend of comfort and convenience. Even better, the 2023 special assessment of $23,000 has been paid in full, covering a new roof, total building painting, and internal pipe lining. This immaculate home features a bright, coastal interior with a serene, open layout and spectacular bay and pool views through the multiple windows only an end unit can offer. The living room and third bedroom are elevated by beautiful moldings and updated ceilings, while the newer kitchen is a chef’s dream with all under-cabinet pull-out drawers and a clever corner turn-around for maximum storage. The bathrooms present an excellent opportunity for a new owner to customize and enhance the space with contemporary finishes. The primary suite is a true retreat, offering breathtaking water views and exceptional closet space with his-and-her built-ins. A unique design feature allows the hallway door to close, transforming the master entry into a private dressing room complete with a full-length mirror. For guests, the hallway is equipped with a pocket door to provide more privacy. The master bedroom also is equipped with a pocket door. Whether you use the expansive third bedroom for visiting family or as a home office, the versatility of the space is unmatched. Step outside and immerse yourself in the beauty of Sarasota Bay, where you'll enjoy direct access to a kayak launch and optional boat slips just steps from your front door. For boating and nature enthusiasts, Bay Harbour is a true gem. Enjoy direct access to a kayak launch and optional boat slips just steps from your front door. With no bridges to Sarasota Bay and just one to the Gulf, you'll have unrestricted access to deep waters for boats up to 42 feet. The remodeled marina is fully equipped with electrical, freshwater, and a fish cleaning station, while the seawall offers frequent visits from dolphins and playful manatees. This unparalleled location is just minutes from world-renowned St. Armands Circle and downtown Sarasota, and it is walkable to the Longboat Key Club, Dry Dock, and Charthouse. Whether you're seeking a permanent residence or a seasonal retreat, this waterfront oasis offers the perfect combination of location, luxury, and lifestyle.

3 Beds ⋅ 2 Baths ⋅ Bay Harbour Apts SubDv. ⋅ 34228 Zip Code

Where can you find an exquisite 3-bedroom waterfront condo on the coveted South End of Longboat Key under $700,000? Discover the ultimate island lifestyle in this beautifully furnished end unit located in the highly sought-after Bay Harbour community. Boasting a desired southern exposure, lower maintenance fees, and a pet-friendly policy, this condo is the perfect blend of comfort and convenience. Even better, the 2023 special assessment of $23,000 has been paid in full, covering a new roof, total building painting, and internal pipe lining. This immaculate home features a bright, coastal interior with a serene, open layout and spectacular bay and pool views through the multiple windows only an end unit can offer. The living room and third bedroom are elevated by beautiful moldings and updated ceilings, while the newer kitchen is a chef’s dream with all under-cabinet pull-out drawers and a clever corner turn-around for maximum storage. The bathrooms present an excellent opportunity for a new owner to customize and enhance the space with contemporary finishes. The primary suite is a true retreat, offering breathtaking water views and exceptional closet space with his-and-her built-ins. A unique design feature allows the hallway door to close, transforming the master entry into a private dressing room complete with a full-length mirror. For guests, the hallway is equipped with a pocket door to provide more privacy. The master bedroom also is equipped with a pocket door. Whether you use the expansive third bedroom for visiting family or as a home office, the versatility of the space is unmatched. Step outside and immerse yourself in the beauty of Sarasota Bay, where you'll enjoy direct access to a kayak launch and optional boat slips just steps from your front door. For boating and nature enthusiasts, Bay Harbour is a true gem. Enjoy direct access to a kayak launch and optional boat slips just steps from your front door. With no bridges to Sarasota Bay and just one to the Gulf, you'll have unrestricted access to deep waters for boats up to 42 feet. The remodeled marina is fully equipped with electrical, freshwater, and a fish cleaning station, while the seawall offers frequent visits from dolphins and playful manatees. This unparalleled location is just minutes from world-renowned St. Armands Circle and downtown Sarasota, and it is walkable to the Longboat Key Club, Dry Dock, and Charthouse. Whether you're seeking a permanent residence or a seasonal retreat, this waterfront oasis offers the perfect combination of location, luxury, and lifestyle.

450 Gulf Of Mexico Drive Unit B207, Longboat Key

6701 Gulf Of Mexico Drive Unit 311, Longboat Key

$620,000

HUGE $50K PRICE REDUCTION - MOTIVATED SELLERS - COASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY: Welcome to a rare opportunity to embrace the BEST of coastal living on Longboat Key. Perched along the pristine shoreline, this meticulously maintained condo offers uninterrupted Gulf of Mexico views—where you can wake up to the gentle sound of waves and witness sunsets that transform the sky into a vibrant masterpiece. UPDATES GALORE: New AC, New Hot Water Heater, New Roof, New Luxury Flooring, New Hurricane Impact Resistant Sliding Doors, New Modern Bathroom. BEING SOLD TURN-KEY. EVERYTHING STAYS! BRIGHT & INVITING INTERIORS: Step inside to discover an open, light-filled layout designed to maximize space and natural beauty. Large glass sliders seamlessly connect the interior to the outdoors, bathing the open kitchen and living area in natural light while blending modern functionality with coastal charm. The thoughtfully designed bedroom and bathroom serve as serene retreats, balancing comfort and style perfectly. YOUR PRIVATE OUTDOOR OASIS: Enjoy a standout private balcony that offers a front-row seat to the endless blue water and sandy beach. Whether savoring a quiet morning coffee or an evening cocktail, the gentle sea breeze creates an ideal setting for relaxation. RESORT-STYLE COMMUNITY AMENITIES: Enhancing your lifestyle, the community boasts a range of well-maintained amenities including: A sparkling pool, Tennis courts, shuffleboard, beach chairs, leasable boat slips, and a tranquil pavilion by the bayou for water enthusiasts. UNMATCHED LOCATION & LIFESTYLE: This condo combines a highly desirable location with the privacy and comfort of a true coastal home—perfect for year-round living, a seasonal retreat, or a savvy investment. Adding to its appeal, the community features exclusively two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, ensuring a streamlined, worry-free living experience. Discover Longboat Key at its finest—where luxury meets laid-back coastal charm. Schedule your private tour today!

1 Beds ⋅ 1 Baths ⋅ Whitney Beach SubDv. ⋅ 34228 Zip Code

HUGE $50K PRICE REDUCTION - MOTIVATED SELLERS - COASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY: Welcome to a rare opportunity to embrace the BEST of coastal living on Longboat Key. Perched along the pristine shoreline, this meticulously maintained condo offers uninterrupted Gulf of Mexico views—where you can wake up to the gentle sound of waves and witness sunsets that transform the sky into a vibrant masterpiece. UPDATES GALORE: New AC, New Hot Water Heater, New Roof, New Luxury Flooring, New Hurricane Impact Resistant Sliding Doors, New Modern Bathroom. BEING SOLD TURN-KEY. EVERYTHING STAYS! BRIGHT & INVITING INTERIORS: Step inside to discover an open, light-filled layout designed to maximize space and natural beauty. Large glass sliders seamlessly connect the interior to the outdoors, bathing the open kitchen and living area in natural light while blending modern functionality with coastal charm. The thoughtfully designed bedroom and bathroom serve as serene retreats, balancing comfort and style perfectly. YOUR PRIVATE OUTDOOR OASIS: Enjoy a standout private balcony that offers a front-row seat to the endless blue water and sandy beach. Whether savoring a quiet morning coffee or an evening cocktail, the gentle sea breeze creates an ideal setting for relaxation. RESORT-STYLE COMMUNITY AMENITIES: Enhancing your lifestyle, the community boasts a range of well-maintained amenities including: A sparkling pool, Tennis courts, shuffleboard, beach chairs, leasable boat slips, and a tranquil pavilion by the bayou for water enthusiasts. UNMATCHED LOCATION & LIFESTYLE: This condo combines a highly desirable location with the privacy and comfort of a true coastal home—perfect for year-round living, a seasonal retreat, or a savvy investment. Adding to its appeal, the community features exclusively two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, ensuring a streamlined, worry-free living experience. Discover Longboat Key at its finest—where luxury meets laid-back coastal charm. Schedule your private tour today!

6701 Gulf Of Mexico Drive Unit 311, Longboat Key

3080 Grand Bay Boulevard Unit 515, Longboat Key

$615,000

Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and kitchen, with double doors allowing the kitchen to be closed off for entertaining. Thoughtfully designed, the kitchen features all-white cabinetry, stone countertops and a clean, timeless aesthetic ideal for both everyday living and hosting. The primary suite is spacious and inviting, with corner sliders opening to the terrace and a well-appointed bath with dual vanities, a spa tub and a glass-walled shower. The guest bedroom is equally generous and enjoys direct terrace access. Outdoors, the expansive terrace offers unobstructed views of Sarasota Bay and the city skyline—perfect for entertaining, morning coffee or evening cocktails. Located behind the gates of Bay Isles, Grand Bay is a socially active, resort-style community offering a clubhouse, guard gate, two-car under-building parking, fitness center, two Har-Tru tennis courts, two heated pools, a spa and deeded access to the private Bay Isles Beach Club. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, private beach privileges, a full-service marina, tennis and pickleball, a luxury spa, fitness facilities and acclaimed dining.

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

Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and kitchen, with double doors allowing the kitchen to be closed off for entertaining. Thoughtfully designed, the kitchen features all-white cabinetry, stone countertops and a clean, timeless aesthetic ideal for both everyday living and hosting. The primary suite is spacious and inviting, with corner sliders opening to the terrace and a well-appointed bath with dual vanities, a spa tub and a glass-walled shower. The guest bedroom is equally generous and enjoys direct terrace access. Outdoors, the expansive terrace offers unobstructed views of Sarasota Bay and the city skyline—perfect for entertaining, morning coffee or evening cocktails. Located behind the gates of Bay Isles, Grand Bay is a socially active, resort-style community offering a clubhouse, guard gate, two-car under-building parking, fitness center, two Har-Tru tennis courts, two heated pools, a spa and deeded access to the private Bay Isles Beach Club. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, private beach privileges, a full-service marina, tennis and pickleball, a luxury spa, fitness facilities and acclaimed dining.

3080 Grand Bay Boulevard Unit 515, Longboat Key

$615,000

We are offering an exceptional investment opportunity at Bayport Beach & Tennis Club. Unit 521 is PRICED BELOW a recent June 2026 independent appraisal and currently the lowest-priced residence in the Bayport Beach & Tennis Club complex, we feel this beautifully updated condominium represents one of the best values on Longboat Key for a primary residence, seasonal retreat, vacation home, or investment property. Features include impact-resistant windows and sliding glass doors, City-permitted interior remodeling, a newer air conditioning system, covered parking, private storage, and numerous thoughtful upgrades throughout. The recent June 2026 independent appraisal, City permit records, association budget, reserve information, and HOA documents are available electronically upon request. Discover the essence of coastal resort living within Bayport's beautifully landscaped 27-acre Gulf-to-Bay community featuring 1,200 feet of private deeded Gulf of Mexico beachfront, direct Sarasota Bay access with a fishing pier and kayak launch, mature tropical landscaping, scenic walking trails, and an outstanding collection of resort-style amenities. Residents enjoy a heated Junior Olympic lap pool, four Har-Tru tennis courts, fitness center, clubhouse, community room, kayak launch and storage, professional on-site management, and one of Longboat Key's most desirable waterfront lifestyles. Conveniently located just minutes from Publix, Ace Hardware, Pickle ball facilities, waterfront dining, boating, championship golf, St. Armands Circle, The Ringling Museum, dog parks, and the cultural attractions of downtown Sarasota, Bayport offers the perfect balance of island tranquility and everyday convenience. Whether you're searching for a full-time residence, seasonal getaway, vacation home, or long-term investment, this move-in-ready residence offers exceptional value in one of Florida's premier Gulf-to-Bay communities. Experience the relaxed elegance, natural beauty, and resort lifestyle that have made Bayport Beach & Tennis Club one of Longboat Key's most sought-after addresses. Come experience why so many residents say that living at Bayport isn't just owning a home—it's embracing a year-round island resort lifestyle that others only experience on vacation.

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

We are offering an exceptional investment opportunity at Bayport Beach & Tennis Club. Unit 521 is PRICED BELOW a recent June 2026 independent appraisal and currently the lowest-priced residence in the Bayport Beach & Tennis Club complex, we feel this beautifully updated condominium represents one of the best values on Longboat Key for a primary residence, seasonal retreat, vacation home, or investment property. Features include impact-resistant windows and sliding glass doors, City-permitted interior remodeling, a newer air conditioning system, covered parking, private storage, and numerous thoughtful upgrades throughout. The recent June 2026 independent appraisal, City permit records, association budget, reserve information, and HOA documents are available electronically upon request. Discover the essence of coastal resort living within Bayport's beautifully landscaped 27-acre Gulf-to-Bay community featuring 1,200 feet of private deeded Gulf of Mexico beachfront, direct Sarasota Bay access with a fishing pier and kayak launch, mature tropical landscaping, scenic walking trails, and an outstanding collection of resort-style amenities. Residents enjoy a heated Junior Olympic lap pool, four Har-Tru tennis courts, fitness center, clubhouse, community room, kayak launch and storage, professional on-site management, and one of Longboat Key's most desirable waterfront lifestyles. Conveniently located just minutes from Publix, Ace Hardware, Pickle ball facilities, waterfront dining, boating, championship golf, St. Armands Circle, The Ringling Museum, dog parks, and the cultural attractions of downtown Sarasota, Bayport offers the perfect balance of island tranquility and everyday convenience. Whether you're searching for a full-time residence, seasonal getaway, vacation home, or long-term investment, this move-in-ready residence offers exceptional value in one of Florida's premier Gulf-to-Bay communities. Experience the relaxed elegance, natural beauty, and resort lifestyle that have made Bayport Beach & Tennis Club one of Longboat Key's most sought-after addresses. Come experience why so many residents say that living at Bayport isn't just owning a home—it's embracing a year-round island resort lifestyle that others only experience on vacation.

521 Bayport Way Unit 521, Longboat Key

$615,000

Wow, I am so Jealous of the Lucky Next owner of this property, What A DEAL!!! Dreaming of living in the Village on Longboat Key? Wow, now is your chance. Don’t miss this Exceptional Opportunity to own a piece of Longboat Key at a remarkable price. Whether you seek a vacation getaway, a permanent island residence, or a lucrative income-producing property ($55k annually rental history), this charming 4-bedroom, 2-bath beach Block home is a perfect fit. Arriving turnkey furnished, this home has been tastefully renovated to ensure a seamless, move-in-ready experience. NEW Roof, NEW Hurricane Windows/Sliders, NEW AC, NEW Appliances, NEW interior, NEW Hot Water Heater. Ready to Go! The heart of the home is a stunning new kitchen, featuring modern cabinetry, huge granite countertops, and premium stainless steel appliances. The thoughtful renovations extend throughout the property, including completely updated bathrooms with contemporary finishes. For your peace of mind, the home has also been upgraded with New Hurricane-Impact Windows throughout, a new AC, an updated electrical system, a new hot water heater and a brand-new roof. Offered TURN-KEY Furnished. The Ultimate Island Lifestyle in Longboat Key’s Coveted Village! Experience the perfect blend of coastal relaxation and modern luxury. Situated on the exclusive north tip of Longboat Key, this meticulously remodeled, move-in-ready home offers a rare opportunity to own a piece of paradise in the heart of "The Village.". The outdoor experience is equally impressive, featuring a large, screened-in porch that overlooks a private backyard with a dedicated fire pit and grilling area—perfect for entertaining. With an outdoor shower and extra gear storage, life here is truly beach-ready. Enjoy the freedom of no HOA in a community where golf carts are the preferred mode of transport. Whether you’re looking for a primary residence or a lucrative investment—currently averaging $55,000 annual rental income with future bookings already in place—this is the ultimate island retreat.

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

Wow, I am so Jealous of the Lucky Next owner of this property, What A DEAL!!! Dreaming of living in the Village on Longboat Key? Wow, now is your chance. Don’t miss this Exceptional Opportunity to own a piece of Longboat Key at a remarkable price. Whether you seek a vacation getaway, a permanent island residence, or a lucrative income-producing property ($55k annually rental history), this charming 4-bedroom, 2-bath beach Block home is a perfect fit. Arriving turnkey furnished, this home has been tastefully renovated to ensure a seamless, move-in-ready experience. NEW Roof, NEW Hurricane Windows/Sliders, NEW AC, NEW Appliances, NEW interior, NEW Hot Water Heater. Ready to Go! The heart of the home is a stunning new kitchen, featuring modern cabinetry, huge granite countertops, and premium stainless steel appliances. The thoughtful renovations extend throughout the property, including completely updated bathrooms with contemporary finishes. For your peace of mind, the home has also been upgraded with New Hurricane-Impact Windows throughout, a new AC, an updated electrical system, a new hot water heater and a brand-new roof. Offered TURN-KEY Furnished. The Ultimate Island Lifestyle in Longboat Key’s Coveted Village! Experience the perfect blend of coastal relaxation and modern luxury. Situated on the exclusive north tip of Longboat Key, this meticulously remodeled, move-in-ready home offers a rare opportunity to own a piece of paradise in the heart of "The Village.". The outdoor experience is equally impressive, featuring a large, screened-in porch that overlooks a private backyard with a dedicated fire pit and grilling area—perfect for entertaining. With an outdoor shower and extra gear storage, life here is truly beach-ready. Enjoy the freedom of no HOA in a community where golf carts are the preferred mode of transport. Whether you’re looking for a primary residence or a lucrative investment—currently averaging $55,000 annual rental income with future bookings already in place—this is the ultimate island retreat.

690 Fox Street, Longboat Key

3500 Gulf Of Mexico Drive Unit 104, Longboat Key

$615,000

Major Price Reduction – Seller Says It’s Time to Sell! Rarely available 3-bedroom, 2.5-bath condo in Buttonwood Cove on Longboat Key, just steps across the street from deeded beach access to the beautiful Gulf of Mexico. This light-filled unit is right across the road from the Gulf with peekaboo views from the front guest bedrooms and full peaceful bay views from all living areas and owners bedroom, creating the perfect island setting from sunrise to sunset. The spacious layout includes an open living and dining area, a private Gulf-facing lanai, and three generously sized bedrooms, providing plenty of room for family and guests. Buttonwood Cove is a boutique waterfront community of only 56 residences offering resort-style amenities including a heated pool, tennis and pickleball courts, fishing pier, kayak launch, and boat docks. Recent community improvements include newer roof, elevators, driveways, exterior paint, and Trex docks, and the association is up to date on milestone inspections. Under-building parking, private storage, and deeded beach access with chairs provided make island living easy. Located just minutes from St. Armands Circle, Longboat Key Club, downtown Sarasota, and SRQ Airport, this is a fantastic opportunity to own a spacious 3-bedroom beachside condo on Longboat Key at a newly reduced price. Seller is motivated — schedule your showing today.

3 Beds ⋅ 3 Baths ⋅ Buttonwood Cove SubDv. ⋅ 34228 Zip Code

Major Price Reduction – Seller Says It’s Time to Sell! Rarely available 3-bedroom, 2.5-bath condo in Buttonwood Cove on Longboat Key, just steps across the street from deeded beach access to the beautiful Gulf of Mexico. This light-filled unit is right across the road from the Gulf with peekaboo views from the front guest bedrooms and full peaceful bay views from all living areas and owners bedroom, creating the perfect island setting from sunrise to sunset. The spacious layout includes an open living and dining area, a private Gulf-facing lanai, and three generously sized bedrooms, providing plenty of room for family and guests. Buttonwood Cove is a boutique waterfront community of only 56 residences offering resort-style amenities including a heated pool, tennis and pickleball courts, fishing pier, kayak launch, and boat docks. Recent community improvements include newer roof, elevators, driveways, exterior paint, and Trex docks, and the association is up to date on milestone inspections. Under-building parking, private storage, and deeded beach access with chairs provided make island living easy. Located just minutes from St. Armands Circle, Longboat Key Club, downtown Sarasota, and SRQ Airport, this is a fantastic opportunity to own a spacious 3-bedroom beachside condo on Longboat Key at a newly reduced price. Seller is motivated — schedule your showing today.

3500 Gulf Of Mexico Drive Unit 104, Longboat Key

1930 Harbourside Drive Unit 136, Longboat Key

$605,000

Sweeping bay views and refined comfort define this beautifully maintained 2BR/2BA residence in Fairway Bay on Longboat Key. A full wall of floor-to-ceiling sliders in the living room frames stunning views of the mangroves and open water, bringing the beauty of the bay into everyday living. Warm wood floors and soft neutral finishes create a classic, welcoming ambiance. The kitchen features rich wood cabinetry, quartz countertops, stainless steel appliances, under-cabinet lighting, and abundant storage. The open layout connects the kitchen, dining, and living areas, extending to the balcony. The spacious primary suite provides a private retreat with balcony access and a well-appointed bath featuring dual vanities, stone counters, a walk-in glass shower, and a separate water closet. The guest suite is equally comfortable, offering both privacy and space for visitors. Residents of Fairway Bay enjoy deeded beach access included through the private Bay Isles Beach Club, a Gulf-front retreat offering shaded cabanas, picnic areas, grills, restrooms, and ample parking—all along one of Longboat Key’s most pristine stretches of beach. Within Fairway Bay, residents also enjoy 24-hour gated security, walking trails, a heated pool, tennis courts, and a fitness center. Optional membership to The Longboat Key Club provides access to 45 holes of championship golf, world-class tennis facilities, a full-service marina, spa and wellness center, multiple dining venues, and an active social calendar. Deepwater slips are also available for boating enthusiasts.

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

Sweeping bay views and refined comfort define this beautifully maintained 2BR/2BA residence in Fairway Bay on Longboat Key. A full wall of floor-to-ceiling sliders in the living room frames stunning views of the mangroves and open water, bringing the beauty of the bay into everyday living. Warm wood floors and soft neutral finishes create a classic, welcoming ambiance. The kitchen features rich wood cabinetry, quartz countertops, stainless steel appliances, under-cabinet lighting, and abundant storage. The open layout connects the kitchen, dining, and living areas, extending to the balcony. The spacious primary suite provides a private retreat with balcony access and a well-appointed bath featuring dual vanities, stone counters, a walk-in glass shower, and a separate water closet. The guest suite is equally comfortable, offering both privacy and space for visitors. Residents of Fairway Bay enjoy deeded beach access included through the private Bay Isles Beach Club, a Gulf-front retreat offering shaded cabanas, picnic areas, grills, restrooms, and ample parking—all along one of Longboat Key’s most pristine stretches of beach. Within Fairway Bay, residents also enjoy 24-hour gated security, walking trails, a heated pool, tennis courts, and a fitness center. Optional membership to The Longboat Key Club provides access to 45 holes of championship golf, world-class tennis facilities, a full-service marina, spa and wellness center, multiple dining venues, and an active social calendar. Deepwater slips are also available for boating enthusiasts.

1930 Harbourside Drive Unit 136, Longboat Key

$600,000

short stories...A rare find buildable lot in historical village of longboat key..Walk across the street for morning coffee.

Long Beach SubDv. ⋅ 34228 Zip Code

short stories...A rare find buildable lot in historical village of longboat key..Walk across the street for morning coffee.

521 Broadway, Longboat Key

4621 Gulf Of Mexico Drive Unit 10D, Longboat Key

$600,000

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

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

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

4621 Gulf Of Mexico Drive Unit 10D, Longboat Key

$600,000

Bingo....You have just found your diamond in the rough—Concrete block home is located just six in from the open Bay. Newer seawall. Two-bedroom home is ready for remodel. The home features 125 ft of canal front frontage and is in a desirable area in that it is situated in between more expensive properties. There is plenty of room for a pool. There is a nice, screened lanai overlooking the canal where one can sit and read a book or sip a cocktail. The kitchen is ready for you to create your own vision. There is also a storage shed for bicycles or garden tools. Many outdoor activities are close by with your deeded beach access at the top of the block and Joan Durante Park a short distance away. There are a handful of restaurants close by so no need to venture too far after a long day at the beach. With its mid-key location, it is easy to head to St Armand Circle, Sarasota or head north to Anna Maria Island. Home is easy to show, and owner has paid Longboat Key Underground Utility Assessment in full. Don’t miss out.... Opportunity knocks and is at your fingertips-

2 Beds ⋅ 1 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Bingo....You have just found your diamond in the rough—Concrete block home is located just six in from the open Bay. Newer seawall. Two-bedroom home is ready for remodel. The home features 125 ft of canal front frontage and is in a desirable area in that it is situated in between more expensive properties. There is plenty of room for a pool. There is a nice, screened lanai overlooking the canal where one can sit and read a book or sip a cocktail. The kitchen is ready for you to create your own vision. There is also a storage shed for bicycles or garden tools. Many outdoor activities are close by with your deeded beach access at the top of the block and Joan Durante Park a short distance away. There are a handful of restaurants close by so no need to venture too far after a long day at the beach. With its mid-key location, it is easy to head to St Armand Circle, Sarasota or head north to Anna Maria Island. Home is easy to show, and owner has paid Longboat Key Underground Utility Assessment in full. Don’t miss out.... Opportunity knocks and is at your fingertips-

780 Jungle Queen Way, Longboat Key

$600,000

Build your dream home on this exceptional vacant lot located in the heart of Longboat Key. Nestled midway on the island, this rare offering includes deeded beach access just a short stroll away, allowing you to enjoy the pristine Gulf shores at your leisure. Perfectly positioned for both privacy and convenience, the property is just moments from the upscale shopping and dining of St. Armands Circle, and the charming waterfront Village of Longboat Key to the north. Enjoy walking distance to grocery stores, boutique shoppes, and local dining, making everyday living effortless. Golf enthusiasts will love quick access to the Harbourside Golf Course at the Longboat Key Club, offering resort-style recreation right next door. With its ideal elevation and location, a future home on this lot could enjoy partial Gulf views, capturing the essence of coastal Florida living. An adjacent lot is also available, presenting a unique opportunity to create a private estate with nearly 300 feet of combined lot frontage—a truly rare find on the island. Endless possibilities await on this coveted stretch of Longboat Key.

Coquina Beach SubDv. ⋅ 34228 Zip Code

Build your dream home on this exceptional vacant lot located in the heart of Longboat Key. Nestled midway on the island, this rare offering includes deeded beach access just a short stroll away, allowing you to enjoy the pristine Gulf shores at your leisure. Perfectly positioned for both privacy and convenience, the property is just moments from the upscale shopping and dining of St. Armands Circle, and the charming waterfront Village of Longboat Key to the north. Enjoy walking distance to grocery stores, boutique shoppes, and local dining, making everyday living effortless. Golf enthusiasts will love quick access to the Harbourside Golf Course at the Longboat Key Club, offering resort-style recreation right next door. With its ideal elevation and location, a future home on this lot could enjoy partial Gulf views, capturing the essence of coastal Florida living. An adjacent lot is also available, presenting a unique opportunity to create a private estate with nearly 300 feet of combined lot frontage—a truly rare find on the island. Endless possibilities await on this coveted stretch of Longboat Key.

2929 Pyrula Drive, Longboat Key

4540 Gulf Of Mexico Drive Unit 204, Longboat Key

$595,000

Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering the best of Longboat Key living with beautiful views of the preserved mangroves and Sarasota Bay. Renovated from top to bottom, this home has been thoughtfully transformed and is available TURNKEY FURNISHED with hurricane impact windows and shutters for a peace of mind. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. A Murphy bed in the office area adds even more versatility, providing the perfect setup for overnight guests while still allowing the space to function as a home office.Living at Windward Bay means embracing the Longboat Key lifestyle from both the BAY AND THE BEACH. Enjoy three beach access points directly across the street for effortless days along the Gulf, while boat slips available to residents make it easy to get out on Sarasota Bay and explore the surrounding waterways. Windward Bay is a PET-FRIENDLY, amenity-rich waterfront community offering multiple swimming pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and scenic walking paths along the bayfront. Ideally situated on Longboat Key, you are just minutes from exceptional restaurants and shopping, St. Armands Circle, Anna Maria Island, and everything Sarasota has to enjoy. With FULLY FUNDED RESERVES FOR 2026, NO UPCOMING SPECIAL ASSESSMENTS, and a PASSED MILESTONE INSPECTION, this move-in-ready residence offers the renovations, amenities, location, and peace of mind today's Florida condo buyer is looking for. Your Longboat Key lifestyle awaits!

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

Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering the best of Longboat Key living with beautiful views of the preserved mangroves and Sarasota Bay. Renovated from top to bottom, this home has been thoughtfully transformed and is available TURNKEY FURNISHED with hurricane impact windows and shutters for a peace of mind. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. A Murphy bed in the office area adds even more versatility, providing the perfect setup for overnight guests while still allowing the space to function as a home office.Living at Windward Bay means embracing the Longboat Key lifestyle from both the BAY AND THE BEACH. Enjoy three beach access points directly across the street for effortless days along the Gulf, while boat slips available to residents make it easy to get out on Sarasota Bay and explore the surrounding waterways. Windward Bay is a PET-FRIENDLY, amenity-rich waterfront community offering multiple swimming pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and scenic walking paths along the bayfront. Ideally situated on Longboat Key, you are just minutes from exceptional restaurants and shopping, St. Armands Circle, Anna Maria Island, and everything Sarasota has to enjoy. With FULLY FUNDED RESERVES FOR 2026, NO UPCOMING SPECIAL ASSESSMENTS, and a PASSED MILESTONE INSPECTION, this move-in-ready residence offers the renovations, amenities, location, and peace of mind today's Florida condo buyer is looking for. Your Longboat Key lifestyle awaits!

4540 Gulf Of Mexico Drive Unit 204, Longboat Key

How much is your home worth?

How much is your home worth?