Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$2,450,000Listed 04/03/2026 10:27AM MLS ID: TB8491404
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3083 Built: 1990 Tax: $20,065 (2025)Community: Marina BayCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$20,065
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Welcome to Marina Bay – the premier condominium within the gated Bay Isles Community on Longboat Key. This exceptional corner residence spans 3,578 sq ft of sunlit, sophisticated living, and shares it fourth floor lobby with only one other unit. The large, updated kitchen/dining room features extra-large windows allowing for an unobstructed view of Sarasota Bay. Exquisite floor-to-ceiling windows, in the oversized living room, frame sweeping panoramic vistas of Sarasota Bay and downtown Sarasota, while the unusually large balcony provides the perfect setting for morning coffee, evening relaxation, and observing abundant bird and marine life. A second, west-facing balcony delivers spectacular Gulf sunsets, offering the rare pleasure of both sunrise and sunset living. Marina Bay is the epitome of resort-style living, with a heated pool and spa, newly renovated tennis and pickleball courts, and well-appointed fitness room. Head to the adjacent marina or around the manicured Longboat Key Club Harbourside Golf Course. Ideally situated, this residence is in close proximity to Publix, CVS, Chase Bank, and local shops. Whether as a refined full-time residence or an elevated part-time retreat, this rare offering delivers unmatched luxury, convenience, and island living. Key Features include: Corner-end unit with 3 bedrooms and 3 ½ newly renovated baths, A walk-in double shower in main suite, New floor tile on oversized screened balcony, bathrooms, and main suite floors, Equipped with storm shutters, and access to private beach for Bay Isles residents only.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,000Listed 04/02/2026 3:28PM MLS ID: A4688148
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2476 Built: 2002 Tax: $19,319 (2025)Community: Bay IslesCondo
Taxes:$19,319
High School: Sarasota High
Remarks: Welcome to Emerald Pointe South in the gated Bay Isles community on Longboat Key. This well-maintained residence offers a light and open floor plan with spacious living and dining areas, ideal for everyday living and entertaining. Sliding glass doors provide abundant natural light and lead to a private screened lanai overlooking lush tropical landscaping. The kitchen features ample cabinetry, solid surface countertops, a breakfast nook, and recent updates including a new microwave, dishwasher, and stove. The primary suite offers dual walk-in closets and an en-suite bath with dual vanities, soaking tub, and separate shower. Two additional bedrooms, each with en-suite baths, are located on the second floor, providing privacy for guests or family. Residents enjoy access to the private Bay Isles Beach Club. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this home offers convenient access to dining, shopping, and beaches. Perfect as a full-time residence or seasonal retreat, this property captures the best of Longboat Key living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$539,000Listed 04/03/2026 10:13AM MLS ID: A4688685
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1214 Built: 1974Monthly Fee: $1,170 Tax: $5,576 (2025)Community: Seaplace ICondo
Taxes:$5,576
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
510 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$4,600,0007 Days on yellowkey MLS ID: A4687207
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 4389 Built: 2013Monthly Fee: $21 Tax: $35,060 (2025)Community: Country Club ShoresSingle Family
Taxes:$35,060
Remarks: One or more photo(s) has been virtually staged. Welcome to this renovated waterfront luxury retreat in the highly sought-after Country Club Shores on Longboat Key. From the moment you arrive to this 5 bedroom 6.5 bathroom almost 4,400 sqft home sitting on nearly ¼ acre, the home’s striking curb appeal, tropical landscaping, and circular paver driveway set the tone for what awaits inside. Perfectly positioned on a deepwater canal with quick access to Sarasota Bay and the Gulf, this exceptional residence offers the ultimate Florida lifestyle with a private dock, 28,000-pound boat lift, and room for a large vessel currently docking a 38 ft boat. Stepping through the front entry, you’re welcomed into a stunning open-concept interior where designer finishes and natural light come together beautifully. The expansive main living area offers soaring coffered ceilings and an impressive floor-to-ceiling marble feature wall complete with an electric fireplace and custom wine display. Large sliding glass doors open wide to seamlessly blend indoor/outdoor living, allowing the waterfront views to become part of everyday living. The gourmet kitchen features top-of-the-line Thermador appliances, custom cabinetry, a wine refrigerator, quartz countertops, and an oversized island with generous seating. The kitchen flows effortlessly into the family room, while the adjacent dining area and breakfast nook offer additional space to gather, all framed by peaceful water views. Privately tucked away on the main floor, the owner’s suite serves as a true retreat. This serene space with plantation shutters offers a luxurious spa-like bathroom complete with dual vanities, quartz countertops, a soaking tub, a walk-in glass shower with a waterfall showerhead, elegant tile finishes, and a Toto Neorest toilet. Upstairs, you’ll find four generously sized bedrooms, each with its own ensuite bathroom and spacious closet, offering comfort and privacy for family or guests alike. One upstairs suite functions beautifully as a secondary primary suite with tray ceilings, dual vanities, and a large walk-in shower with dual showerheads. An upstairs media room adds flexibility and is the perfect place for movie nights, game days, or relaxed entertaining, while the upper-level terrace provides another place to unwind and take in the surrounding waterfront views. An elevator services the garage, first floor, and second floor, adding everyday ease and convenience. Outside, the backyard was designed to feel like your own private resort. The heated saltwater pool and spa are surrounded by travertine tile, tropical landscaping and spacious lounging areas, all overlooking the water for a tranquil setting. A full pool bath adds functionality for seamless indoor-outdoor living. Whether you're spending the afternoon poolside, entertaining under the sun, or heading out for a sunset cruise from your private dock, this home delivers the kind of waterfront lifestyle buyers dream about. Located in the coveted Country Club Shores community, this exceptional property also offers deeded beach access to the powder-soft Gulf beaches just moments away. Enjoy being only minutes from the world-class golf, tennis, dining, and marina amenities of Longboat Key Club, along with the upscale shopping and restaurants of St. Armands Circle, the arts and culture of downtown Sarasota, and the convenience of SRQ International Airport. This is more than just a home, it’s a luxury coastal lifestyle in one of the area’s most desirable waterfront communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kaisen Mitchell (941-726-7657)
531 WEDGE LN, LONGBOAT KEY, FL 34228
$2,599,999Listed 04/02/2026 5:10PM MLS ID: A4687694
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2751 Built: 1966Monthly Fee: $21 Tax: $10,602 (2025)Community: Country Club Shores Sec 02Single Family
Taxes:$10,602
Remarks: A seamless blend of refined design and waterfront living defines this beautifully updated canal-front residence in Country Club Shores. Expanded from its original ranch design, the home offers approximately 2,700+ square feet of thoughtfully curated space, featuring four bedrooms, including dual primary suites on both the first and second levels—an ideal layout for guests or multi-generational living. Each bathroom is finished with timeless, elegant details that elevate the home’s overall sense of sophistication. A comprehensive 2018 renovation introduced elevated style and modern functionality, anchored by a stunning chef’s kitchen appointed with Thermador appliances, built-in refrigeration, and a generous island. Just beyond, an expansive butler’s pantry and secondary prep kitchen enhance both convenience and flow, creating an effortless environment for everyday living and entertaining. Natural light fills the interiors, drawing attention to tranquil canal views and soft glimpses of the bay from the den. The upstairs primary suite serves as a private retreat, complete with its own balcony overlooking the water—an inviting setting for quiet mornings and sunset evenings. Outdoors, a private, low-maintenance setting unfolds with a sparkling pool and beautifully updated waterfront features, including a newer dock, seawall, and 24,000 lb boat lift. Additional highlights include hurricane-impact windows and doors, classic plantation shutters, and 2022 air conditioning systems—completing this exceptional offering in one of Longboat Key’s most desirable waterfront communities. Ideally located just moments from St. Armands Circle, with its renowned dining and boutique shopping, this residence offers a lifestyle of effortless coastal sophistication.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kerry Mccarthy (720-233-7147)
561 BIRDIE LN, LONGBOAT KEY, FL 34228
$2,195,0001 Day on yellowkey MLS ID: A4687002
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2256 Built: 1967Monthly Fee: $17 Tax: $15,946 (2025)Community: Country Club ShoresSingle Family
Taxes:$15,946
Remarks: This mid-canal gem in the heart of the prestigious Country Club Shores perfectly balances immediate enjoyment with future possibilities. Whether you are looking for a private boating retreat, a "saltwater lake house," or a high-performing seasonal rental investment, this 3-bedroom, 3-bathroom block construction home delivers “all of the above”, and boasts an oversized lot! The residence is centered around open gathering space, wrapped by 3 private bedrooms (2 en-suite!), an inviting kitchen, and a 2-car garage, all sheltered under a metal roof installed in 2019. A refreshing pool completes the oasis. For water enthusiasts, the 2019 waterside upgrades transform the back yard into a premier private marina. The NEW SEA WALL and 350-square-foot dock make an angler’s paradise, complemented by a 13,000-pound boat lift and a floating kayak launch. Navigation is exceptionally convenient with no low bridges blocking your path to adventure. You are a one-minute boat ride to Sarasota Bay and only five minutes to the Gulf of Mexico. Proximity to both the Sarasota Yacht Club and Bird Key Yacht Club further expands the nautical recreation offered by this phenomenal address. Lifestyle activities extend well beyond the dock, with deeded beach access just a seven-minute stroll away, and quick access to the world-class Longboat Key Club for golf enthusiasts. Perhaps the most compelling feature of this home is its remarkable resilience and elevation – it remained high and dry during the area’s most challenging weather, sustaining zero damage or water intrusion during hurricanes Milton, Helene, and Ian. In fact, there is no evidence of any storm damage throughout the entire history of the home. This level of peace of mind is a rare luxury for coastal living, ensuring your investment remains as sturdy and secure as it is beautiful. If you envision eventually building a grander "forever home," the unique dimensions of this lot offer a distinct architectural advantage. With almost 1000 sqft more than the neighborhood's typical 100x100 lots, you have an additional 282 square feet of allowable building coverage. This property is a versatile coastal sanctuary that offers a rare blend of ready enjoyment and significant long-term potential.
Listing Agent: Mairead Smialek (847-334-4848)
2800 HARBOURSIDE DR #E-07, LONGBOAT KEY, FL 34228
$300,000Listed 04/02/2026 1:06PM MLS ID: A4688599
Bed: Bath: 0.0 Built: 1985Monthly Fee: $372 Tax: $2,230 (2025)Community: Longboat Key Moorings MarinaDock-Rackominium
Taxes:$2,230
Remarks: A favorite dock in the Marina with ample turning radius. This 55 x 21 foot slip at Longboat Key Club Moorings is located on the west side of the Marina. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,00017 Days on yellowkey MLS ID: A4686552
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1981 Tax: $6,376 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$6,376
Remarks: Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit offers two expansive bedrooms and two beautiful bathrooms and comes fully turn-key. This unit was curated with attention to detail and functionality in mind. The kitchen offers plenty of storage, stainless steel appliances, quartz countertops and beautiful accent details. Enjoy three patios that allow for great indoor/outdoor living. Fully equipped with Hurricane impact doors and windows. One under building parking space included, along with a locked storage closet - perfect for bikes and beach gear. When not at the beach, enjoy the meticulously kept nature trails, landscaped grounds and wildlife. Just steps away from the well appointed clubhouse is equipped with a Junior-Olympic sized heated pool, four har-tru tennis courts, a fitness center and more. In addition, Bayport residents are proud of their active social and recreational calendar. Water enthusiasts can utilize the secluded fishing pier that stretches out onto Sarasota Bay; to fish, watch the sunrise, the Manatees swim or the Egrets wading among the mangrove trees. Residents also benefit from conveniently located on-site paddle board and kayak launch and storage areas. Bayport residents enjoy an array of restaurants locally, and the convenience of a nearby supermarket, pharmacy and boutique shops. Recreational enthusiasts also benefit from the nearby Bayfront Park which offers a popular pickle-ball program, dog park and other bayside activities. The nearby Longboat Key Club offers private access to championship waterfront golf, extensive leisure activities and boating facilities. Within minutes, one can access the famous St Armand's Circle with its exceptional shopping and dining amenities. From there, cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Alexis Smith-Frady (352-225-1724)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,00042 Days on yellowkey MLS ID: A4683021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $17,930 (2025)Community: Beaches Of Longboat KeyCondo
Taxes:$17,930
Remarks: Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
1912 HARBOURSIDE DR #604, LONGBOAT KEY, FL 34228
$850,00035 Days on yellowkey MLS ID: A4683819
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1316 Built: 1982 Tax: $7,734 (2025)Community: Fairway Bay 1Townhouse
Taxes:$7,734
Remarks: Embrace the island life style within the gates of Longboat Key's premier resort community of Bay Isles. You'll love this spacious townhome-style condo in Fairway Bay. Designed with soaring ceilings and large windows to allow maximum light and expansive views of the neighborhood’s tropical foliage, this beautifully and thoughtfully renovated home offers lots of space for gatherings with friends or family. The main living area opens effortlessly to a screened porch through sliding doors, creating a bright and airy space perfect for entertaining. The open floorplan, cozy fireplace, freshly painted interiors, fully updated kitchen and bathrooms, two bedrooms, and abundant storage make this home as functional as it is inviting. Downstairs, a flexible bonus space off the oversized 2-car garage offers endless possibilities. This bonus area includes a spacious living room, a flex space (currently set up as a 3rd bedroom), a full bath, and laundry room – perfect for guests, hobbies, or working from home. Just a few steps away, enjoy one of the community’s pools and hot tubs, or explore all the amenities this vibrant neighborhood offers – another heated pool and hot tub, miles of manicured paths, a clubhouse, fitness center, tennis/pickleball courts, and 24-hour gated security. Plus, gain deeded access to the Bay Isles Beach Club, a private, gated Gulf-side retreat with a covered pavilion, parking, restrooms, grills, a beach volleyball court, and sunsets that will take your breath away. This home truly lives like a retreat. Just 10 miles from Anna Maria Island to the North, South 4 miles to St. Armands Circle, and another 4 to Downtown Sarasota, with plenty of shopping, dining, and entertainment options. Your tropical beach getaway is ready and waiting – come make it yours!
Listing is courtesy of: S&N REAL ESTATE, INC. (941-320-5482)
Listing Agent: Darlena Nelms (941-320-5482)
2600 HARBOURSIDE DR #C13, LONGBOAT KEY, FL 34228
$489,50021 Days on yellowkey MLS ID: A4686064
Bed: Bath: 0.0 Monthly Fee: $411 Tax: $2,681 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,681
Remarks: 72' x 21' Boat Slip on C-Dock at Longboat Key Moorings Marina for Sale ~ AND THERE IS NO MEMBERSHIP REQUIREMENT to join The Longboat Key Club (which is now $115,000) and the annual fee of $8388 plus food & beverage fees. The beauty of this TWO-LEVEL dock is... there is no covenant BUT if you chose to join the Longboat Key Club, there are multiple membership packages to choose from which give you access to multiple restaurants, the beach club and poolside restaurants, more information can be provided upon request. The Longboat Key Moorings is strategically located on the beautiful exclusive island of Longboat Key ~ just a few minutes to St. Armands Circle, downtown Sarasota or Bradenton Beach. This amazing location provides direct access to Sarasota Bay and the ICW and the Gulf of America. The LBK Moorings is a deep water ~ state-of-the art marina ~ offering full services, with a touch of class and personal attention seldom found elsewhere. World class facilities on this spectacular island provides storm-protected deep water yacht slips, Dock Crew, Harbor Concierge, 24-hour manned Guard Gate and much more. Each slip has Cable TV, Electricity, Water and Wi-Fi. There also is an on-site service department for repair and maintenance needs, as well as, on-site fuel service, and pump out service. An amazing location with quick access to great shops and dining at St Armands Circle and from there a Classic Sarasota Trolley will take you into downtown Sarasota and back! Your Gateway to the Gulf! Imagine stepping aboard your boat just minutes from the sparkling waters of the Gulf of Mexico. This exceptional boat slip in beautiful Longboat Key offers the perfect combination of convenience, protection, and access for serious boaters and coastal lifestyle lovers alike. Perfectly positioned for effortless cruising, this dock provides quick, unobstructed access to the open waters of the Gulf—no long no-wake zones or complicated navigation. From here, you’re only moments away from world-class fishing, sunset cruises, and exploring the stunning coastline. Owning a dock in Longboat Key means more than just a place to park your boat—it’s an invitation to enjoy sun-drenched days on the water, dolphin sightings, world-class fishing, and unforgettable sunsets. Why This Location Stands Out • Quick boating access to Sarasota Bay and the Gulf • Close to waterfront dining, marinas, and fuel • Situated in one of Florida’s most sought-after boating communities Rare Opportunity Boat slips in Longboat Key are highly coveted and rarely available. Whether you’re a local boater, seasonal resident, or investor looking for premium waterfront access, this is your chance to secure a piece of paradise.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Rian Carver (941-735-6010)
3030 GRAND BAY BLVD #323, LONGBOAT KEY, FL 34228
$1,250,00059 Days on yellowkey MLS ID: A4681067
1 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1998 Tax: $9,798 (2025)Community: Grand Bay 3Condo
Taxes:$9,798
Remarks: This sought-after 2,550 sq. ft. Cayman model in Grand Bay is located within the community’s desirable Building III and ideally positioned to capture magnificent Sarasota Bay and sparkling city views, with additional vistas overlooking the Harbourside Golf Course. Approximately 700 square feet of outdoor living includes two expansive terraces: an east-facing for breathtaking sunrises over the bay and a west-facing showcasing unforgettable glowing sunsets. A private elevator foyer opens to the spacious living area with 9-foot ceilings and immediate “wow” views of the bay. The primary suite is thoughtfully positioned for privacy, featuring serene bay views, a sliding glass door to the bayfront terrace, and an updated primary bathroom with dual bath areas. The guest bedroom is located on the west side of the residence with direct access to the west-facing terrace. The den, considered an occasional 3rd bedroom, offers exceptional flexibility with two sets of concealed movable doors allowing this space to be closed off from the kitchen and dining areas for privacy, and it enjoys access to a third full bath. The dining room is centrally located, enhancing the open flow between living spaces while offering both bay and west-exposure views. The kitchen includes a breakfast room and abundant cabinetry. Luxury vinyl flooring runs throughout the residence. The condominium is being sold partially furnished for the new owner to begin their coastal journey with ease. Grand Bay residents enjoy an exceptional array of resort-style amenities, including two heated pools & spas, two Har-Tru tennis courts, a state-of-the-art fitness center with sauna, 24-hour guard-gated security, and on-site management. Miles of sidewalks and trails wind throughout the natural beauty of Bay Isles, a true sanctuary for nature lovers. Bay Isles Beach Club membership is included exclusively for owners, offering gated parking and private beach access with beach amenities, grills, and conveniences. Optional Longboat Key Club membership, including golf, is also available.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3060 GRAND BAY BLVD #174, LONGBOAT KEY, FL 34228
$1,939,00088 Days on yellowkey MLS ID: R4910478
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1994Monthly Fee: $2,617 Tax: $17,500 (2024)Community: Grand Bay 1Condo
Taxes:$17,500
Elementary School: None
Tax Year: 2024
Remarks: PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
1281 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$1,050,0004 Days on yellowkey MLS ID: A4688079
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 1999 Tax: $9,956 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$9,956
Remarks: Welcome to a little piece of paradise on Longboat Key at the stunning gated Gulf-front condominium community of Water Club, which offers a coastal lifestyle complete with direct access to sandy beaches, high-end amenities and exceptional security and concierge services. This designer-inspired, furnished two-bedroom, 2.5-bath condominium is on the newer north building's plaza level and features nearly 1,400 square feet, 10-foot ceilings, double crown molding, plank wood flooring in the living areas, natural colors and floor to ceiling storm impact windows and doors. An open floor plan offers garden views from the spacious living room and the kitchen, which has both a breakfast bar and a seating area. A beautiful kitchen renovation was completed in December 2025 with handsome wood cabinets, stone countertops and GE Profile appliances. The split plan allows privacy for owners and guests in the two separate primary en-suite bedrooms, each with large windows, custom drapes and carpet, wall closets with built-ins and baths with combination tub/showers. ?An expansive balcony with glass railing barriers can be accessed through the living area and one of the primary suites. This lovely condo conveniently has a stack washer and dryer, linen closet, underbuilding storage unit and assigned parking and its own front desk concierge. Behind the 24-hour guarded-gate is true luxury living with a modern clubhouse, state-of-the-art fitness room, locker room and spa, sauna, bar and lounge, library, game room, ballroom and catering kitchen and outside terrace for gatherings and watching sunsets over the Gulf waters. Besides the magnificent beach and Florida-friendly landscaped grounds, the outdoor amenities include a peaceful courtyard, fire pit, resort-style pool and hot tub and new Har-tru tennis courts. Water Club is conveniently near island golf courses and Publix, and a short distance from St. Armands Circle and downtown Sarasota for dining, shopping, entertainment and cultural venues.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kathleen Ucci (941-302-2344)
2165 GULF OF MEXICO DR #115, LONGBOAT KEY, FL 34228
$2,350,00034 Days on yellowkey MLS ID: A4684194
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2485 Built: 1996 Tax: $12,382 (2025)Community: Villa Di Lancia Ph 1Condo
Taxes:$12,382
Remarks: Experience and enjoy breathtaking, unobstructed Gulf views from this exceptional “walk-down” corner 3-bedroom 3-bath residence in the prestigious Villa Di Lancia community on South Longboat Key. Fully updated and spanning 2,485 sq. ft., this residence feels like its own private beachfront home. Upon entering from the semi-private elevator lobby, you are welcomed into an open and light-filled floor plan with soaring 10-foot ceilings and expansive walls of glass. As one of the most desirable corner residences in the community, this residence showcases panoramic Gulf views from nearly every room, which can be enjoyed by an additional wall of windows that flood the interior with natural light. The expansive great room connects to a nearly 500 sq. ft. covered terrace — your front-row seat to spectacular sunsets over turquoise waters! The terrace also has a private staircase allowing direct access to the beach and Gulf-front pool and spa, creating a rare and seamless indoor-outdoor lifestyle. The updated eat-in kitchen features a serving bar, walk-in pantry, full laundry room, and generous storage. The split floor plan allows owners and guests alike to enjoy quiet privacy. The primary suite is a true retreat, complete with direct Gulf views, private terrace access, spacious closets, and a large en-suite bath. The guest wing includes a second en-suite bedroom, as well as a third bedroom or a convenient and flexible den space with an adjacent bath. Villa Di Lancia is an exclusive boutique community with only 38 residences with resort-style amenities. Relax by the heated Gulf-front pool and spa, or enjoy friendly competition on the Har-Tru tennis and pickleball courts, as well as a state-of-the-art fitness center and steam room. Resort-style living has been effortlessly achieved throughout the community, including the newly updated clubhouse, social room and kitchen, on-site management, 24-hour manned gate, EV charging station, secure under-building parking, guest parking, and a private storage room. This welcoming community is both pet-friendly and impeccably maintained. Ideally located on the southern end of Longboat Key, residents enjoy proximity to fine and casual dining, golf, marinas, shopping, St. Armands Circle, and Sarasota’s cultural attractions. Residences here are rarely available. This is a rare opportunity to own a luxurious beachfront sanctuary and experience refined coastal living at its finest. This residence feels like a beautiful private home on the beach!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$2,795,000157 Days on yellowkey MLS ID: A4669837
Bed: 3 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3045 Built: 1996 Tax: $25,341 (2024)Community: Water Club 01 At Longboat KeyCondo
Taxes:$25,341
Remarks: Welcome to The Water Club at Longboat Key, where privacy, spaciousness, and resort-style amenities complement the natural beauty of the setting at the edge of the sparkling waters of the Gulf of Mexico. Residents benefit from a semi-private elevator that opens directly into an impressive foyer, offering sweeping views of Sarasota Bay and the city skyline through floor-to-ceiling windows. This residence is on the north side of the south building, the sunset view side, overlooking the beautiful pool deck amenity of the community. This eighth-floor Brighton residence is highly coveted for its three-bedroom configuration with panoramic vistas of the Gulf, beach, and bay from two expansive terraces. Features include ten-foot ceilings, extensive glass walls, and storm protection shutters , enhancing both comfort and sophistication. The living room is designed to maximize openness and showcase sunsets over the Gulf. The primary suite offers a private terrace, den, walk-in closet, and dual bathrooms. With a split-bedroom plan, privacy is maintained for two generous guest suites, each featuring an en-suite bath. The kitchen is efficiently appointed with significant storage and a breakfast area overlooking the water. The Water Club stands as Longboat Key’s premier gated beachfront community, situated on 16 acres of meticulously landscaped grounds. Amenities include a 17,000-square-foot clubhouse, well-equipped fitness center and spa, heated lap pool and hot tub, four Har-Tru tennis courts, concierge services, and versatile gathering spaces such as a library, billiards room, ballroom, firepit, and grilling area. Additional conveniences include under-building parking, climate-controlled storage, on-site management, and 24-hour security. Ideally located on the south end of Longboat Key, residents enjoy proximity to Longboat Key Club golf facilities, Publix shopping center, exclusive St. Armands Circle, downtown Sarasota’s cultural offerings, and Sarasota International Airport, just 20 minutes away. The Water Club is pet-friendly and impeccably maintained, providing the pinnacle of coastal luxury living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228
$1,559,00028 Days on yellowkey MLS ID: A4684840
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2579 Built: 1998Monthly Fee: $833 Tax: $17,916 (2025)Community: Bay IslesSingle Family
Taxes:$17,916
Remarks: Nestled behind the gates of Queens Harbour in Bay Isles, this exceptional single-story home offers a rare blend of privacy, space, and effortless Longboat Key living—perfectly positioned on a quiet cul-de-sac with sweeping views along the 4th hole of the Longboat Key Club’s Blue Heron golf course. Spanning approximately 2,579 sq. ft., the thoughtfully designed floor plan features three bedrooms, two full baths, and a half bath, with flexible spaces that adapt beautifully to your lifestyle. A large, dedicated office/den with beautiful glass French doors and custom cabinetry offers outstanding flexibility and can serve as an additional sleeping space if desired. Inside, soaring 14-foot ceilings, rich wood flooring, and an open living-and-dining layout create an airy, welcoming atmosphere. A generous great room is framed by walls of sliding glass doors, opening to the pool and patio for seamless indoor-outdoor living—ideal for entertaining or simply unwinding with tranquil golf course views. The kitchen is perfectly placed for everyday living and gathering, featuring solid wood cabinetry, stone countertops, a center island with a veggie sink, pantry storage, a gas cooktop, and stainless-steel appliances. Two generous guest suites are ideally situated in this split plan, sharing a full bath with the ability to be closed off from the main living area. The private primary suite is a true retreat with golf course views across your private pool and spa. The spa fountain’s soft, flowing water creates a soothing backdrop that drifts into the bedroom through the sliding door access to the patio. The spacious bedroom features a walk-in closet, additional wall closet and a well-appointed en-suite bath with dual sinks, a soaking tub, separate shower, and private water closet. Outdoors, enjoy the screened private pool and spa with multiple seating areas and ample room to lounge and entertain in total comfort. The home has been immaculately maintained and includes new pool equipment and pool heater, a resurfaced pool, tile roof (2020), tankless gas water heater, as well as several additional upgrades – perfect move-in condition. Queens Harbour residents enjoy a maintenance-free lifestyle with 24-hour guard-gated security, with a community heated pool and spa just across the street. Ownership also includes deeded access to the private Bay Isles Beach Club, offering Gulf-front pavilions, grilling areas, multiple beach volleyball courts and a pristine beach only minutes away. Perfectly located within the gates of the Resort at Longboat Key Club’s Harborside Golf course and 290 slip deep-water Moorings marina, and close to island dining—plus easy access to St. Armands Circle, Lido Beach, and downtown Sarasota—this golf course home delivers the space, privacy, and location that define Longboat Key at its best.
Listing Agent: Kathy Callahan (941-900-8088)
100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
$950,00089 Days on yellowkey MLS ID: A4676681
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $3,929 (2025)Community: Sands PointCondo
Taxes:$3,929
Remarks: GREAT PRICE REDUCTION !!!! MUST SEE ARCHITECTURAL GEM on Longboat Key! Sands Point Condominium is a best kept secret along the beautiful crystal white sands of Longboat Key. This community blends gorgeous mid-century architecture with the stunning location tucked away next to Longboat Key Club. Sands Point offers everything you need to relax and unwind under the Florida sun and all the amenities you could ask for including a private marina. Whether you are a vacationer or full- time resident, you will find this New Pass location one of the best on the island encompassing stunning sunset views. This two bedroom unit is filled with sunlight and has had extensive renovations/remodel (2023) throughout. The beautiful luxury flooring and tall baseboards extend throughout the entire unit. The expansive combination living/dining spaces offer room for large groups or to allow for separate seating areas; all without giving up glorious sunny views. The gorgeous kitchen offers stainless steel Samsung appliances including a French door refrigerator with 2 freezer drawers range and microwave. The double stainless steel sink is a plus for those who love to cook. Beautiful stone countertops top fresh white cabinetry with soft-close doors and drawers. A generous pantry holds all the supplies you need for cooking and entertaining. Dual sides cabinetry forms the breakfast bar offering even more storage. The interior laundry room has GE Insignia washer and dryer and add cabinetry and shelving for storage. Both bathrooms are updated with new cabinetry and countertops. The Primary bedroom is a huge space with a wall of windows; a bright, airy space with ample room for a desk and has both a built-in and a walk-in closet. Both the Primary Suite and the large great room space have stunning views of the Marina. Mid-century charm exudes from the social room gathering space; terrazzo floors and complementing furnishings make this a fun space to gather and entertain. The space includes a kitchen and library area. There is onsite management housed in this building as well. A short walk takes you to the stunning beach-exactly what you come here for! Expansive white sand beach area wraps around the complex. Palapas, beach chairs and a newly renovated pool area overlooks New Pass. Watch the dolphin and enjoy spectacular sunsets. The marina complex offers boat slips on a first come/first serve basis and offers a kayak launch, fishing pier, storage and bicycle storage areas. HVAC new in 2020,. The condo offers an assigned covered parking spot right and a separate assigned storage unit. St Armands Circle, with a variety of restaurants and shops is a short drive away. Easy access to downtown Sarasota and its cultural and entertainment venues. You must see this home to fully appreciate the charm, history and expansive coveted location on the beach of Sands Point. Don't fight the crowds and traffic to enjoy the beach; you are here!!!
Listing is courtesy of: WAGNER REALTY (941-751-0670)
Listing Agent: Donna Turnbaugh (410-382-4692)
1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$1,075,000112 Days on yellowkey MLS ID: A4674194
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1707 Built: 1983 Tax: $11,336 (2025)Community: Players Club IvCondo
Taxes:$11,336
Remarks: Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000197 Days on yellowkey MLS ID: A4665247
Bed: 1 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1556 Built: 2025 Tax: $25,560 (2025)Community: St. Regis Longboat KeyCondo
Taxes:$25,560
Remarks: Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.
Listing Agent: Kim Ogilvie (941-951-6660)
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