Location: Longboat Key
Do Not Show Listings
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,350,000197 Days on yellowkey MLS ID: A4667938
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3045 Built: 1996 Tax: $31,926 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$31,926
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom plus oversized study, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include two under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3010 GRAND BAY BLVD #493, LONGBOAT KEY, FL 34228
$1,879,000196 Days on yellowkey MLS ID: A4668143
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1999 Tax: $16,976 (2025)Community: Grand Bay 4Spa: YesCondo
Taxes:$16,976
Remarks: One or more photo(s) has been virtually staged. Perched just one floor below the penthouse in the sought-after Grand Bay IV community on Longboat Key, this 2,550-sq.-ft. Cayman floor plan offers an exceptional opportunity to enjoy the Grand Bay lifestyle immediately—while still allowing a future owner to complete their personal renovation plans once the building’s elevator modernization is finished. The furniture rental will extend for up to one year, giving the buyer time to enjoy the residence while preparing for future customization or construction. With ideal north–south exposure, this residence captures breathtaking sunrises over Sarasota Bay and stunning Gulf sunsets from two expansive terraces. Walls of glass and abundant natural light enhance the open-concept layout, which includes 2 bedrooms, 2.5 baths, and a den that can easily be reconfigured to include a walk-in closet for a 3rd bedroom. The primary suite opens directly to the Bayfront terrace, the second bedroom offers an en-suite bath and private Gulf-view balcony, and the den, kitchen, and third bedroom share access to a second terrace for effortless indoor-outdoor living. Two prime, side-by-side parking spaces on the upper main level sit conveniently next to the elevator, leading to a private elevator foyer. Residents of Grand Bay enjoy world-class amenities including 24-hour security, a clubhouse with library and game room, fitness center, tennis and pickleball courts, two heated pools and a spa, and deeded access to the exclusive Bay Isles Beach Club.
3030 GRAND BAY BLVD #323, LONGBOAT KEY, FL 34228
$1,250,00080 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 3Spa: YesCondo
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.
1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,195,00056 Days on yellowkey MLS ID: A4684021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2092 Built: 1982 Tax: $11,749 (2025)Community: Players Club IiiSpa: YesCondo
Taxes:$11,749
Remarks: Step into this highly desirable corner residence featuring three bedrooms, three full baths, and an expansive 36’ x 11’ sunroom at The Players Club. You’ll immediately be drawn to the impressive 31-foot balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. Inside, the sun-filled kitchen is thoughtfully designed with custom cabinetry and a built-in breakfast table that expands both workspace and storage. It flows seamlessly into the main living and dining areas, creating a warm and open environment for entertaining or daily living. Just off the kitchen, elegant French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The owner’s suite provides a private sanctuary with a spa-inspired bathroom featuring a soaking tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. The second bedroom functions as a true secondary master, complete with dual sinks, a full vanity, and a fitted walk-in closet, offering comfort and privacy for family or visitors. A third bedroom adds flexibility for guests, workspace, or hobbies. A unique feature of this residence is the private garage, offering rare security and convenience for residents, plus an additional covered parking space underneath the building for extra guest or secondary vehicle use. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves. Just minutes from St. Armands Circle, downtown Longboat Key, and Longboat Key Club, with championship golf, premier tennis, and a deep-water marina, this corner residence blends privacy, convenience, and resort-style coastal living. Units with this versatile layout and resort-ready features are highly sought after. Offered partially furnished. Seller is willing to discuss a subsidy on the quarterly condominium fee for reserve increase over the next two years!
5055 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$565,00057 Days on yellowkey MLS ID: A4683419
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $8,183 (2024)Community: Club Longboat Beach & TennisSpa: YesCondo
Taxes:$8,183
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Discover an exceptional value opportunity in Club Longboat on Longboat Key, one of the island’s most desirable beachside communities known for its active lifestyle and resort style amenities. This three bedroom, two bathroom ground floor walkout residence is currently the least expensive unit in the community and presents a rare chance to create a fully customized coastal retreat. With a solid existing layout and desirable ground level access that enhances indoor / outdoor living, the residence offers tremendous flexibility. Buyers have the opportunity to redesign and expand the third bedroom to add additional square footage, whether to create a more spacious primary suite, an inviting guest retreat, or a dedicated office or flex space. The potential to transform this residence into a personalized showpiece is exceptional. Club Longboat is ideal for tennis, pickleball, and beach enthusiasts, offering eight Har Tru tennis courts with three lined for pickleball, two heated swimming pools, and 750 feet of private Gulf front beachfront complete with lounge chairs and umbrellas. The serene waterfront setting enhances the peaceful atmosphere and scenic surroundings. The residence includes a covered parking space directly in front of the unit along with abundant guest parking. On site management serves the 85 residences, providing convenience and peace of mind within a welcoming, all ages community. Owners enjoy a pet friendly environment with no weight restrictions and a flexible rental policy allowing one month minimum rentals up to twelve times per year, creating excellent income potential. Conveniently located near shopping and fine dining, this is a rare opportunity to secure a value driven property in an amenity rich Longboat Key beachfront community and make it entirely your own.
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$1,225,00032 Days on yellowkey MLS ID: A4686721
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
1932 HARBOURSIDE DR #242, LONGBOAT KEY, FL 34228
$599,00011 Days on yellowkey MLS ID: A4688978
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982Monthly Fee: $81 Tax: $7,099 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$7,099
Middle School: Pine View School
Remarks: Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This turnkey furnished move-in ready two-bedroom, two-bathroom residence presents an exceptional chance to enjoy the Longboat Key lifestyle along with the rare advantage of one under building garage parking space. Enjoy peaceful views of Sarasota Bay, surrounding mangroves, and native wildlife from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ready for immediate enjoyment as a primary home, seasonal retreat, or investment opportunity. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.
2251 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$5,999,000287 Days on yellowkey MLS ID: A4658325
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3921 Built: 2016Monthly Fee: $7,501 Tax: $69,970 (2024)Community: Aria Longboat KeySpa: YesCondo
Taxes:$69,970
Remarks: One or more photo(s) has been virtually staged. Welcome to an exceptional Gulf-front residence within the prestigious Aria community on the coveted south end of Longboat Key where refined coastal living meets timeless elegance. Set along 300 feet of pristine private shoreline, this extraordinary property offers a rare opportunity to experience true beachfront luxury in one of Sarasota’s most exclusive enclaves. Beyond the gated entrance, Aria unveils a serene, resort-inspired setting with lush native landscaping, tranquil walking paths, and the historic Villa am Meer, a beautifully restored 1935 seaside mansion that serves as the community’s elegant social centerpiece. This impeccably designed residence spans nearly 4,000 square feet and is accessed via a private elevator, opening to a grand foyer and expansive, light-filled interiors. The thoughtfully curated open-concept floor plan seamlessly integrates sophisticated living and dining spaces with a chef’s kitchen, creating an ideal environment for both everyday living and elevated entertaining. Walls of floor-to-ceiling glass and soaring ceilings invite natural light while framing sweeping, unobstructed views of the Gulf. Expansive wraparound terraces provide the perfect setting to enjoy breathtaking sunsets and coastal breezes from nearly every room. The gourmet kitchen is a statement of both form and function, featuring premium quartz surfaces, custom wood cabinetry, and top-tier appliances by Wolf and Miele. The primary suite serves as a private sanctuary, offering a spa-inspired retreat with dual baths connected by an oversized walk-in shower an exceptional design element rarely found. Two additional ensuite bedrooms provide luxurious accommodations for guests, while a dedicated office or optional fourth bedroom adds versatility. A bonus room offers additional flexibility for hobbies, media, or storage. Residents of Aria enjoy an unparalleled suite of amenities, including a beachfront pool and spa, state-of-the-art fitness and yoga studios, massage room, and a private wine cellar. A full-time onsite caretaker ensures a seamless, service-oriented lifestyle. The residence also includes a private, oversized two-car dehumidified garage.
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Woodruff, Pa (941-705-8686)
5591 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$900,0002 Days on yellowkey MLS ID: A4690629
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1979 Tax: $3,532 (2025)Community: Sea Club IiiSpa: NoCondo
Taxes:$3,532
Elementary School: None
High School: None
Middle School: None
Remarks: Experience coastal living at its finest in this beautifully remodeled (2025) Gulf-front, ground-floor end unit at sought-after Sea Club III on Longboat Key. Sea Club III's daily and weekly rental flexibility accommodates those seeking to maximize rental income potential and/or enjoy that perfect personal retreat and getaway. No driving to beach parking lots or crossing streets for amenities required. Enjoy the convenience of direct Gulf beach access with powdery sands, soothing waters and breathtaking sunsets. All just steps from your covered patio. Heated community pool just steps from your front entry. Step inside to find fully furnished and updated interiors (2025). Impact double pane windows and sliders (2025) for added comfort and peace of mind. This condo offers both tranquility and accessibility. Sea Club III is just a short stroll to dining, cafés and parks. Located just minutes from St. Armands Circle and Downtown Sarasota’s dining, shopping and art scene. Convenient to SRQ airport with its ever-increasing direct flights to Sarasota. Do not miss out. This is truly a rare opportunity to own a piece of Old Florida!
Listing is courtesy of: WAGNER REALTY (941-761-3100)
Listing Agent: Gina Uliano (941-920-0276)
2109 GULF OF MEXICO DR #1303, LONGBOAT KEY, FL 34228
$1,075,000102 Days on yellowkey MLS ID: A4677817
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1463 Built: 1984 Tax: $9,654 (2025)Community: Sunset BeachSpa: YesCondo
Taxes:$9,654
Remarks: Discover effortless beachfront living in this beautifully furnished and renovated 2-bedroom, 2-bath residence. A rare opportunity to own a refined boutique beachfront escape of only 65 residences—where sophistication meets the relaxed elegance of Gulf Coast living. Captivating Gulf views are enjoyed from EVERY room. The light and airy interior welcomes you with a sun-filled, open-concept layout framed by floor-to-ceiling impact glass windows capturing breathtaking Ocean vistas. The living, dining, and kitchen spaces connect seamlessly, creating a welcoming environment for both entertaining and everyday relaxation. The renovated kitchen is thoughtfully designed for modern coastal living, complete with Cambria quartz countertops, an oversized island perfect for meal prepping as well as breakfast seating, LG stainless steel appliances, and soft-close cabinetry complete the package. Step onto the private balcony to enjoy morning coffee or evening cocktails as spectacular vibrant sunsets unfold over the water and paint the sky. The primary suite serves as a tranquil coastal sanctuary, featuring expansive Gulf views, the gentle rhythm of the surf, spacious walk-in closet, and a beautifully appointed ensuite bath. The guest bedroom provides both privacy and beautiful water views, making it ideal for hosting friends and family. An interior laundry room with additional cabinetry adds convenience and functionality. Covered under-building parking and additional storage complete this exceptional offering. Sunset Beach, an intimate private beachfront community without the crowds of a larger complex but still offers resort-inspired amenities including a heated pool, spa, fire pit, BBQ grills, and direct access to powdery white sand beaches just beyond your doorstep. Ideally positioned near St. Armands Circle, the Longboat Key Club, marinas, dining, shopping, and entertainment, this home offers the perfect balance of location and coastal beauty. A rare opportunity to own an exceptional Gulf-front retreat designed for the relaxed rhythm of island life. (Second bedroom virtually staged)
Listing Agent: Wendy Leventhal (941-376-4894)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,00063 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)
100 SANDS POINT RD #108, LONGBOAT KEY, FL 34228
$925,00022 Days on yellowkey MLS ID: A4688092
4 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $6,063 (2025)Community: Sands PointCondo
Taxes:$6,063
High School: Sarasota High
Remarks: Welcome to Sands Point on fabulous Longboat Key: A unique mid-century modern gem situated behind the gates of Longboat Key Club on a tranquil stretch of beach along the sparkling Gulf of Mexico and the inlet of New Pass. This 2 bdrm/2 bath walk-out looks out to the sparkling turquoise waters and you can stroll right out from your back patio in the sugary sand to the one of a kind beachside pool. The gorgeous, wide beach just beyond is complete with tiki huts and loungers for your absolute enjoyment. A perfect spot to sit back and enjoy this incredible coastal paradise. The community lives like a resort and offers it's own little marina, there is a waitlist for slips but it provides a great spot to fish from the seawall, or launch your kayaks and paddleboards. When you're ready for more, just over the bridge is world famous St.Armands Circle filled with restaurants and shopping and the cultural mecca of downtown Sarasota is just moments from there. Schedule your private showing and come imagine what true island living on Longboat Key is all about.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
1912 HARBOURSIDE DR #602, LONGBOAT KEY, FL 34228
$549,900189 Days on yellowkey MLS ID: A4668394
1 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1590 Built: 1982 Tax: $6,146 (2024)Community: Fairway Bay 1Spa: YesCondo
Taxes:$6,146
Remarks: Under contract-accepting backup offers. NEWLY painted bright and fresh INTERIOR. Discover the ideal blend of comfort, convenience, and coastal charm in this beautifully furnished townhouse in Fairway Bay, a sought-after, gated community within Bay Isles on Longboat Key. Enjoy easy access to the gorgeous Gulf beach of Longboat Key via a private beach club, and an abundance of activities, including biking, recreation, pickleball and tennis, ideal for those who embrace an active lifestyle. The main level of this townhome offers an open, eat-in kitchen with a breakfast bar that flows effortlessly into the inviting living room, complete with a wood-burning fireplace and large sliding doors leading to a screened lanai with stairs to the outdoors. A convenient half bath completes this level, making it ideal for entertaining. Upstairs, the primary suite features a spacious walk-in closet and a private en-suite bath with double sinks. A second bedroom, also with its full en-suite bath, provides comfort and privacy for guests. The laundry is conveniently on this upper level. On the garage level, you’ll find a large storage room and a bonus space, offering endless possibilities such as a home gym, hobby area or even a space for guests. Fairway Bay homeowners have access to the on-site clubhouse, where there are social activities, a community gym and Har-Tru tennis courts for residents only. Fairway Bay is in Bay Isles, where you have 24/7 gated security and deeded access to the beautiful and private Bay Isles Beach Club. Here you can enjoy gated parking, restrooms, beach chair and umbrella storage, an ice machine, refrigerator and microwave, the ideal place for barbecues, picnics, and sunset gatherings with family and friends. Furniture is included, making this an effortless move-in opportunity to start enjoying the Longboat Key lifestyle from day one. This home is in proximity to Longboat Key Club where you have 45 holes of golf, a world-class tennis center, pickleball courts and five private restaurants accessible to you with additional membership. It’s rare to find a home in Bay Isles offering this level of lifestyle, amenities and value. Don’t miss this opportunity to live your best life on Longboat Key and start making memories of a lifetime today.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Judy Mitchell (941-275-6838)
1930 HARBOURSIDE DR #145, LONGBOAT KEY, FL 34228
$549,00018 Days on yellowkey MLS ID: A4686987
REDUCED by $50,000 (8.3%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982 Tax: $8,215 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$8,215
Remarks: Set on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residence captures sweeping views across the mangroves, a navigable channel and Sarasota Bay beyond—creating a vibrant waterfront backdrop from nearly every room. Upon entry, engineered wood flooring draws your eye to a wall of glass at the rear of the residence, where shifting blue and green tones take center stage. The layout flows effortlessly from the updated kitchen into the dining area and living room, allowing the view to remain the focal point throughout. The kitchen has been thoughtfully redesigned with striking stone countertops, low-profile white cabinetry, a refined tile backsplash and stainless-steel appliances. The living room opens to an expansive terrace through a full wall of sliders, offering a front-row perspective of the mangroves and channel, where boats pass by and manatees are often seen gliding through the water—creating a setting that feels both peaceful and connected. The primary suite serves as a private retreat with rich wood flooring, direct terrace access and a well-appointed bath featuring dual vanities and a separate water closet. The guest bedroom is comfortably sized, and the guest bath has also been tastefully updated. Residents of Fairway Bay enjoy a bayside lifestyle with deeded beach access through the private Bay Isles Beach Club, one underbuilding parking space, 24-hour gated security, walking trails, a heated pool, tennis courts and a fitness center. Membership opportunities at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available, and small pets up to 15 pounds are welcome.
Listing Agent: Bruce Myer (941-376-5311)
3040 GRAND BAY BLVD #283, LONGBOAT KEY, FL 34228
$1,799,000179 Days on yellowkey MLS ID: A4669347
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2550 Built: 1996 Tax: $18,262 (2025)Community: Grand Bay 2Spa: NoCondo
Taxes:$18,262
Remarks: Welcome to Grand Bay. Experience the essence of refined coastal living, where breathtaking panoramic water and city views take center stage. Awaken to the sunrise over Sarasota Bay’s skyline with limitless views of the bay and golf course, and unwind with stunning sunsets over the Gulf, an ever-changing display of beauty from every room. Perfectly situated on the 8th floor, this elegant home welcomes you through a private-access, controlled elevator leading to a stunning foyer framed by contemporary glass double doors. The Cayman open floor plan immediately reveals sweeping vistas, while large porcelain tile flooring flows seamlessly through the living areas and onto two outdoor terraces ideal for quiet relaxation. The stunning updated kitchen features two-toned cabinetry, Wolf and Sub-Zero appliances, under-cabinet lighting, quartz countertops, and an inviting breakfast bar. An adjacent eat-in area with floor-to-ceiling sliders opens to a private covered terrace, a perfect setting for entertaining guests and boundless vistas. The primary suite is a lavish retreat, complete with white oak floors, two walk-in closets and a spa-inspired bath showcasing, a soaking tub, glass shower, and dual vanities. The guest suite offers private terrace access for stunning sunset views, complemented by white oak floors and an en-suite bath. Discover versatility with a den/office that doubles as an occasional guest room, providing privacy with elegant pocket doors that separate it from the formal dining room, and a 3rd full bath just steps away. A well thought out conversion has added a built-in office area adding functionality to round out the interior. Residents enjoy various first-rate amenities, including 24-hour guard gates, a clubhouse, two community pools and spas, a large fitness center with saunas, and tennis courts. Stroll the neighborhood’s scenic walking paths or enjoy deeded access to the exclusive gated Bay Isles Beach Club offering locker rooms, barbecues, volleyball nets, covered picnic areas and a sandy white beach. Located behind the Bay Isles secure gates, this secluded neighborhood rests on the rolling greens of the Longboat Key Club’s golf course. Grand Bay residents find it hard to leave this special community. This residence truly captures the best refined Bay and beach lifestyle – sophisticated, exclusive, and ready to be enjoyed.
Listing Agent: Stacy Hanan (941-266-0529)
5635 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228
$1,050,00063 Days on yellowkey MLS ID: A4683336
2 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1786 Built: 1980 Tax: $13,341 (2024)Community: Longboat SandpipersCondo
Taxes:$13,341
Remarks: Under contract-accepting backup offers. Welcome to Sandpipers, a boutique Gulf-front condominium community on the desirable north end of Longboat Key. This well-maintained second-floor residence offers 2 bedrooms, 2 bathrooms, and 1,786 square feet of relaxed coastal living. The home has been meticulously cared for with classic finishes and a show-stopping view. Step onto the private, screened lanai and take in soothing Gulf breezes, the sound of the waves, and spectacular sunsets over the Gulf of Mexico. The expansive lanai creates an inviting indoor-outdoor living space, perfect for morning coffee or evening relaxation. Residents of the 10-unit Sandpipers community enjoy private beach access and a community pool. The residence is offered furnished, making an easy transition into island living. Conveniently located close to St. Armands Circle, downtown Sarasota, and the coastal charm of Anna Maria Island. This is a rare opportunity to own a spacious and thoughtfully laid-out Gulf-front condo in one of Longboat Key’s most desirable boutique communities. Schedule your private showing today.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: April Green (941-773-1680)
4380 EXETER DR #H-103, LONGBOAT KEY, FL 34228
$649,900123 Days on yellowkey MLS ID: A4675171
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $7,333 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$7,333
Remarks: Welcome to this beautifully updated first-floor waterfront condominium offering two bedrooms, two bathrooms, and a glass-enclosed lanai, all sold for effortless coastal living. Enjoy tranquil canal views with passing boats and frequent manatee sightings, delivering an authentic Florida waterfront experience right outside your door. The open-concept kitchen has been fully remodeled and features granite countertops, new cabinetry, stainless steel appliances, ceramic tile flooring, and fresh interior paint. Tile floors extend throughout the main living areas, while new carpeting enhances the comfort of the second bedroom. Both bathrooms were tastefully renovated in 2022, and a new A/C system installed in 2021, Hurricane Windows and Doors , ensure year-round comfort and peace of mind. Offered fully furnished, this inviting residence includes tasteful décor, artwork, and kitchenware, making it ideal for immediate occupancy, seasonal use, or investment. Located within Longboat Harbour, a gated waterfront community, residents enjoy an impressive collection of resort-style amenities. Highlights include deeded private beach access with a beachfront pavilion featuring gated Gulf access, restrooms, hot showers, lockers, parking, and a convenient car wash area. Additional amenities include boat docks, four heated pools, a recently updated clubhouse with banquet hall, library, arts and crafts room, billiards and card rooms, a fully equipped fitness center, tennis and pickleball courts, barbecue grills, kayak storage, and additional storage rooms. When available, boat slips accommodating vessels up to 34 feet are offered for a nominal annual fee. This is a rare opportunity to own a turnkey waterfront residence on the ground floor with exceptional amenities in one of Longboat Key’s most desirable communities. Call today to set up your private showing!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Andrew Haddad (941-313-1218)
4234 GULF OF MEXICO DR #G2, LONGBOAT KEY, FL 34228
$849,000341 Days on yellowkey MLS ID: A4653045
REDUCED by $46,000 (5.1%) on 04/21/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1636 Built: 1973 Tax: $13,273 (2024)Community: Pelican Harbour & Beach ClubCondo
Taxes:$13,273
Remarks: Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony. The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street. Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports. Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value.
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Shauna Ruby (941-544-2070)
2295 GULF OF MEXICO DR #23S, LONGBOAT KEY, FL 34228
$1,295,000184 Days on yellowkey MLS ID: A4669226
REDUCED by $100,000 (7.2%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $9,812 (2024)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$9,812
Remarks: Set directly on the shores of the Gulf of Mexico, this beautifully renovated residence in the Islander Club captures the essence of Longboat Key beachfront living. Located in the desirable South Tower, this 2BR/2BA home showcases a fresh coastal design with wide-plank flooring, crown molding, recessed lighting, and an open layout oriented to the water. The kitchen exudes coastal charm with stone countertops, shaker cabinetry, stainless-steel appliances, and a sea-glass tile backsplash. Both baths have been redone with refined finishes, glass-enclosed showers, and clean modern tilework. Floor-to-ceiling sliders open to an expansive covered terrace—perfect for outdoor dining, lounging, and taking in sweeping Gulf views. The primary suite also enjoys terrace access and an endless horizon of turquoise water. Residents of the Islander Club enjoy 400 feet of private beach, a Gulf-front pool, fitness center, tennis courts, pickleball, library, social lounge, and on-site management within two secure towers and gated entry. The recently updated common areas - including the elegant lobby and clubroom - offer a stylish, contemporary ambiance overlooking the Gulf. Ideally positioned near St. Armands Circle and Sarasota’s world-class dining, shopping, and cultural attractions, this residence offers an effortless blend of comfort, sophistication, and beachfront tranquility.
600 SUTTON PL #B302, LONGBOAT KEY, FL 34228
$500,0007 Days on yellowkey MLS ID: A4690036
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1132 Built: 1973Monthly Fee: $1,642 Tax: $7,415 (2025)Community: Sutton PlaceSpa: NoCondo
Taxes:$7,415
Middle School: W.D. Sugg Middle
Remarks: Enjoy the best of the Longboat Key lifestyle in this beautifully updated 2-bedroom, 2-bath waterfront condo at Sutton Place, offering a rare Gulf-to-Bay experience with Sarasota Bay views and PRIVATE DEEDED BEACH ACCESS to a Gulf-front beach just across the street. This light and bright residence features a spacious, open floor plan with quality finishes throughout, including porcelain tile and engineered hardwood flooring for a clean, modern, low-maintenance feel. The updated kitchen is both stylish and functional, showcasing quartz countertops, a mother-of-pearl mosaic backsplash, tray ceiling, and stainless steel appliances. The primary suite includes a fully remodeled bathroom with quartz counters, custom glass shower, and marble tile, while the guest bathroom features granite countertops and a vessel sink. A glass-enclosed and screened lanai extends the living space, bringing in natural light and allowing you to enjoy peaceful bay breezes year-round. Recent upgrades include newly installed IMPACT RESISTANT WINDOWS & DOORS, providing added safety, energy efficiency, and peace of mind. Updated lighting was also added in the living area This residence is being sold TURNKEY FURNISHED, making it truly move-in ready or ideal as a second home or investment property. As an added bonus, the sale includes four brand new KAYAKS—perfect for enjoying the community’s direct bay access and embracing the waterfront lifestyle. Sutton Place is a highly desirable waterfront community offering exceptional amenities, including deeded Gulf beach access with pavilion, gated parking, showers, and picnic areas, TWO heated bayside POOLS, BBQ grills, BOAT SLIPS (first-come, $300/year), kayak storage and launch, fishing dock, clubhouse, and covered parking with ample guest spaces. The community is pet-friendly (2 pets up to 25 lbs each), not age restricted, and allows two rentals per year with a one-month minimum after the first year of ownership, making it ideal for both personal use and investment. Recent community improvements include new roofs, exterior repainting, and resealing (2023), along with a completed milestone inspection. Ideally located mid-key, close to Bayfront Park, dining, shopping, and just a short drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. Don’t miss this opportunity to own a piece of paradise on Longboat Key.
Listing Agent: Debbie Mchardy (941-960-6099)
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