Location: Longboat Key
Do Not Show Listings
5055 GULF OF MEXICO DR #435, LONGBOAT KEY, FL 34228
$600,000150 Days on yellowkey MLS ID: A4671314
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $7,986 (2024)Community: Club Longboat Beach & TennisCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,986
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Peek-a-boo Gulf views from back deck in this open concept 2-Bedroom, 2-Bathroom Condo at Club Longboat Beach & Tennis Resort. This Longboat Key Retreat offers an expansive 1,484 SqFt of thoughtfully designed living space and combines comfort, convenience. There are 2 balconies one off the living room and the second off the master bedroom. Watch a game of tennis and enjoy the salt air as you unwind with your favorite drink. This is a well maintained residence and some upgrades include: (new HVAC 2025, hot water heater, stainless fridge), this home offers a welcoming, move-in ready atmosphere and provides a sanctuary where you can enjoy both peaceful living and the energy of Longboat Key's vibrant community. Longboat Key is renowned for its pristine beaches, relaxed atmosphere, and upscale lifestyle. With easy access to fine dining, shopping, cultural attractions, and outdoor recreation, it’s the ideal location for those seeking a laid-back coastal lifestyle, while still being close to the excitement of Sarasota. Whether you’re taking a morning stroll on the beach or enjoying the world-class amenities nearby, Longboat Key offers a unique blend of tranquility and activity. Club Longboat Beach & Tennis is more than just a place to live – it’s a destination where every day feels like a vacation. The resort has an expansive calendar full of activities outdoors and the clubhouse has gatherings and various events. Enjoy direct access to the beautiful white sands of Longboat Key Beach, perfect for sunbathing, swimming, and watersports. The community offers resort-style amenities, including meticulously maintained tennis courts, a fitness center, a heated pool (one of which is private for adults only), and 24-hour security. Whether you’re looking to relax poolside or stay active with tennis or fitness, there’s something for everyone. Don’t miss out on the opportunity to own your slice of paradise.
Listing is courtesy of: COASTAL KEY REALTY LLC (941-993-9380)
Listing Agent: Amy Jones (941-993-9380)
6800 GULF OF MEXICO DRIVE #184, LONGBOAT KEY, FL 34228
$475,00025 Days on yellowkey MLS ID: A4687722
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1287 Built: 1970 Tax: $6,630 (2025)Community: Whitney BeachCondo
Taxes:$6,630
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Beautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private beach across the way, this 2nd floor island retreat is located in a charming Gulf-to-Bay community, nestled between the azure blue water of the Gulf of Mexico and serene Bishops Bayou, where Manatees & Dolphins play. This lovely 2nd level end-unit features an open floor plan, enhanced by a gorgeous designer kitchen with quartz countertop & backsplash and bronze hardware, which overlooks the dining-living room combo, all offering Gulf views. The Florida room overlooks one of the two sparkling swimming pools, which are at your disposal. Hurricane resistant sliding doors and windows offer peace of mind, and the roof has recently been replaced. Luxury vinyl flooring extends all the way through the living space, including the primary suite, which is tucked away for optimal privacy. The screened front patio is the perfect spot to relax and enjoy the turquoise water views, and there is a 9' x 5' storage room for all your toys. Just bring your flip flops & beach wear and start enjoying the laid-back island lifestyle. Two heated pool, tennis & pickleball courts, 23 boat slips, a vintage boathouse/clubhouse, grilling stations, kayak launch, shuffleboard, private deeded beach directly across the road with gazebos and beach lounges plus those amazing sunsets. Two large pets are welcome and the condo can be rented 6 times per year with one month minimum. After a fun-filled day kayaking, beach strolling, fishing or boating, first-class restaurants and casual eateries are located within a short walk, bike or boat ride. Coffee, smoothie & donut shops, liquor store, 24-hour gym, Pilates studio & beauty salon, boutiques and more are just a block away. Don't miss this wonderful opportunity to make your dreams of living on Longboat Key come true!
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
1211 GULF OF MEXICO DR #610, LONGBOAT KEY, FL 34228
$1,395,00062 Days on yellowkey MLS ID: A4682918
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1827 Built: 1985 Tax: $14,561 (2025)Community: PromenadeCondo
Taxes:$14,561
Remarks: Positioned on the south side and sixth floor of The Promenade on Longboat Key, Residence #610 delivers a true move-in-ready coastal retreat with sweeping Gulf-to-bay views that unfold the moment you enter. From sunrises over Sarasota Bay to sparkling views across the Gulf of Mexico, nearly every room captures water vistas that define the island lifestyle. Offered fully furnished, this updated residence showcases a refined blend of travertine and rich wood flooring, crisp architectural lines, and an abundance of natural light pouring through expansive glass sliders. The open living and dining areas are framed by walls of glass that lead to the private terrace—an ideal vantage point for morning coffee overlooking the Gulf or evening relaxation with the shimmer of bay and downtown skyline vistas in the distance. The contemporary kitchen is thoughtfully designed with sleek surfaces, ample cabinetry, and generous counter space, flowing seamlessly into the main living areas for effortless entertaining. The bright ambiance continues into the bedrooms, where large windows highlight panoramic water and skyline views while maintaining a sense of privacy and comfort. The split-bedroom floor plan ensures privacy, with a spacious primary suite offering dual walk-in closets, terrace access, and an en-suite bath with dual sinks, soaking tub, separate shower, and private water closet. The guest suite includes a walk-in closet and its own en-suite bath, ideal for visitors or seasonal stays. Every detail reflects a residence that has been meticulously maintained and is ready for immediate enjoyment—whether as a full-time home or seasonal escape. The Promenade is a gated, Gulf-front community known for its exceptional amenities and attentive service. Residents enjoy a 24-hour manned guard gate, concierge services, on-site management, secure lobby, health club facilities for men and women, social rooms, four Har-Tru tennis courts, a Gulfside sundeck, and an oversized heated swimming pool and spa. A private boardwalk leads directly to the beach that elevate everyday coastal living. Situated on the south end of Longboat Key, The Promenade offers convenient access to the Longboat Key Club’s golf and marina facilities (access is available with separate memberships), waterfront dining, and nearby shopping. St. Armands Circle and downtown Sarasota are just minutes away, where boutiques, theaters, art galleries, and renowned restaurants define the Cultural Coast lifestyle. Promenade #610 presents a rare opportunity to enjoy turnkey beachfront living with panoramic water views, resort-style amenities, and proximity to everything that makes Longboat Key and Sarasota so desirable.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,350,000193 Days on yellowkey MLS ID: A4667938
Bed: 3 Bath: 4.0 Liv Area Sq Ft: 3045 Built: 1996 Tax: $31,926 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$31,926
Elementary School: Southside Elementary
High School: Booker High
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 Agent: Ryan Ackerman, Pa (305-205-7700)
6381 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$5,995,00088 Days on yellowkey MLS ID: A4678978
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 4224 Built: 2021 Tax: $94,565 (2025)Community: Sleepy LagoonSingle Family
Taxes:$94,565
Remarks: One or more photo(s) has been virtually staged. Welcome to a once-in-a-lifetime opportunity to own a sleek, modern coastal estate on one of Longboat Key’s most coveted stretches of sand. Perfectly situated on a rare double lot on the beach side of Gulf of Mexico Drive, this architectural gem incorporates uninterrupted, panoramic views of the Gulf. This completely turnkey furnished 4,420 square foot home has 4 bedrooms, 5 bathrooms and includes many upgrades showcasing incredible style. With nothing ever to be built in front, those golden sunsets and turquoise seas can be yours to savor forever. Built in 2021 with no expense spared, this home is a fortress of strength. Designed for durability by a structural architect, this home is constructed entirely of concrete utilizing sheer walls and concrete block combined with over-engineered pilings for peace of mind. Reglet trim has been achieved by utilizing metal steel framing , providing longevity and function. Inside, dramatic Euro-wall sliders blur the boundaries between indoors and outdoors, leading to a wraparound terrace that offers sweeping 260-degree views. A stunning elevated infinity-edge pool and spa, an outdoor shower and a fire table provide endless enjoyment. Level 5 drywall, oversized porcelain tile floors, and high design finishes elevate every corner. The main living level features a dazzling chef’s kitchen with European lacquer cabinetry, quartzite counters, and top-of the-line appliances: a 48” Sub-Zero fridge, 48” gas range, two ice makers, wine fridge, microwave drawer, natural gas service and more. Lutron LED lighting enhances the crisp, contemporary ambiance. The outdoor living is equally luxurious utilizing matching porcelain tile and a walnut-lined covered terrace to flow seamlessly from the interior. The top floor is a true penthouse master suite, leading to a self-contained oasis. The spa-like bathroom includes a soaking tub, a huge walk in shower and Gulf views from every room. An additional 1,150 square foot upper patio deck is framed by huge sliders allowing true indoor/outdoor living. In addition there is a second laundry room and kitchenette creating an amazing sanctuary. Whether used as a private refuge or separate guest quarters, this space can be closed off from the rest of the home, allowing the second floor, which includes 3 bedrooms and 3.5 baths, to be independently rented while preserving your own private haven. Three garages accommodate up to 9 vehicles, a gym and recreational toys. Leading outside is a large open area providing room to add a pickleball court or putting green. Beyond is over an acre of public land owned by the town of Longboat Key insuring your forever Gulf views. Additional perks include an elevator, two-zone A/C, dual laundry setups, gas tankless water heater, and electronic shades throughout. Currently operating as The Sea Grape Inn, this home offers income potential without sacrificing privacy, making it a rare hybrid of luxury retreat and smart investment. Step from your door to the sugar-white sands of Longboat Key and experience the pinnacle of Gulf-front living.
2525 GULF OF MEXICO DR #6B, LONGBOAT KEY, FL 34228
$1,425,000137 Days on yellowkey MLS ID: A4673235
1 Days Off yellowkey (back on 3/27/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1491 Built: 1972 Tax: $15,702 (2024)Community: Islands WestCondo
Taxes:$15,702
Remarks: Under contract-accepting backup offers. Ultra-luxury, fully remodeled Gulf-front residence on Longboat Key. This sixth-floor, move-in ready condo at Islands West comes furnished and showcases imported Italian cabinetry, level 5 drywall, carrara marble flooring, aqua quartz countertops and steam shower. All-new hurricane-impact windows and doors, including floor-to-ceiling glass in both bedrooms, frame sweeping water views and a desirable southern exposure. It also includes brand new 2.5 ton AC with extended warranty, Bosch French door refrigerator and Bosch cooktop. The 1,491-square-foot layout features two bedrooms with ensuite baths, a spacious great room, open kitchen/dining area, and a convenient storage closet. The split-bedroom design enhances privacy, and the guest suite includes a walk-in closet with Bosch stackable washer and dryer. A generous 21' x 10' balcony extends the living area outdoors for year-round enjoyment. Islands West is a 15-story, resort-style community set directly on the sands of the Gulf of Mexico, offering secure key fob entry, social room with library, two fitness rooms, catering kitchen, heated beachfront pool and spa, dry sauna, outdoor patio and grills, tennis courts with pickleball lines, and storage for bikes, kayaks, and paddleboards. Two pets are allowed. Across the street, Bay Isles Shoppes has Publix, CVS, dining, banking and daily conveniences, with Longboat Key Tennis Center, Bayfront Park, multiple marinas, St. Armands Circle and downtown Sarasota all just a short drive away.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Nancy Endara (941-323-1700)
5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$7,800,000123 Days on yellowkey MLS ID: A4673495
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4630 Built: 2018Monthly Fee: $572 Tax: $30,971 (2024)Community: Bonaire At Longboat KeySingle Family
Taxes:$30,971
Remarks: Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
531 SUTTON PL, LONGBOAT KEY, FL 34228
$529,00073 Days on yellowkey MLS ID: A4681208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1972 Tax: $1,900 (2025)Community: Sutton PlaceCondo
Taxes:$1,900
Remarks: Your easy island escape awaits in the beach-to-bay community of Sutton Place on Longboat Key. Spend your days at the deeded Gulf beach, lounging by one of two heated pools, kayaking on the bay, or heading out on the water—all within the community. This two-bedroom townhome is ideal for seasonal or year round living, offering impact windows and doors, steel roof trusses, and a private oversized garage for bikes, beach chairs, and island gear. The renovated kitchen features quartz countertops and Bosch appliances, and both bedrooms include walk-in closets and fully tiled baths. Unwind on two enclosed balconies overlooking a tranquil pond, then lock up and travel with confidence. Centrally located mid-island, Sutton Place offers the perfect blend of resort-style amenities in a beautiful setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Sherri Mills (941-350-7112)
2410 HARBOURSIDE DR #142, LONGBOAT KEY, FL 34228
$2,695,00042 Days on yellowkey MLS ID: A4685398
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 3382 Built: 1993Community: Marina BayCondo
Taxes:
Tax Year:
Remarks: Positioned on the fourth floor of Marina Bay Building I, this fully renovated bayfront residence offers sweeping views across Sarasota Bay and the Harbourside Golf Course from one of Longboat Key’s most exclusive gated communities. Encompassing more than 3,300 square feet of interior living space, this three-bedroom, three-and-a-half-bath residence blends the scale and privacy of a single-family home with the convenience of condominium living. From the moment you enter, walls of floor-to-ceiling glass sliders and oversized windows frame panoramic water and golf course vistas while filling the home with natural light. The open great-room layout creates a comfortable flow between the living, dining, and entertaining spaces, enhanced by engineered hardwood flooring, crown molding, custom built-ins, tray ceilings, and thoughtfully designed lighting. The chef’s kitchen was completely redesigned in 2024, showcasing custom shaker-style cabinetry, quartzite countertops, and an extended island finished in complementary natural wood. High-end appliances include a Viking induction range, Miele built-in coffee station, wine refrigerator, and reverse-osmosis filtration system. A tile backsplash, pantry storage, and built-in planning desk complete this functional and beautifully designed culinary space. The kitchen connects seamlessly to the casual dining area and adjacent media room, creating an ideal setting for everyday living and entertaining. Additional improvements include two new HVAC systems installed in 2025 and remote-controlled storm shutters on all waterfront openings installed in 2024, offering comfort, efficiency, and peace of mind. The primary suite serves as a private waterfront retreat with direct terrace access and serene bay views. Renovated in 2024, this spacious suite features dual walk-in closets with built-in storage systems, and an updated en-suite bath offering dual vanities, soaking tub, and glass-enclosed shower. Two additional guest suites are positioned on the west side of the residence in a split layout, each with walk-in closets, en-suite baths, and access to a shared terrace for visiting family and guests. Secure under-building parking and elevator access add everyday convenience. Marina Bay is an intimate waterfront community of only 60 residences, located behind the gates of Bay Isles. Residents enjoy 24-hour guard-gated security, on-site management, a fitness center, tennis courts, grilling area, and a heated bayfront swimming pool and spa with a scenic sundeck. Ownership also includes deeded access to the private Bay Isles Beach Club, where residents enjoy Gulf-front pavilions, gated parking, and direct access to the white-sand beaches of Longboat Key. Ideally located on the south end of the island, Marina Bay is just minutes from Harbourside Golf Course, the Longboat Key Club marina, and waterfront dining. St. Armands Circle offers boutique shopping and restaurants nearby, while downtown Sarasota’s theaters, galleries, and cultural venues are only a short drive away. From boating and golf to sunset walks along the Gulf, this residence places the best of Longboat Key and Sarasota living within easy reach.
2425 GULF OF MEXICO DR #1E, LONGBOAT KEY, FL 34228
$1,450,000151 Days on yellowkey MLS ID: A4672789
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973Community: Sea Gate ClubCondo
Remarks: One or more photo(s) has been virtually staged. Welcome to this rarely available Seagate direct beachfront residence, where unmatched coastal living meets exceptional convenience. Step from your private terrace straight onto the sand, an experience that truly defines beachfront living. Perfectly situated across from the Publix Bay Isles Shopping Center and just moments from the world-famous Longboat Key Club and Resort, this location offers the best of Longboat Key at your doorstep. This beautifully renovated two-bedroom, two-bath residence, just under 1,500 square feet, features a bright, open floor plan with stunning Gulf views from every room. The split-bedroom layout provides two generously sized suites with abundant storage. Designer finishes shine throughout, and no detail has been overlooked. The chef’s kitchen boasts Quartz countertops, custom backsplash tile, bright white cabinetry, new appliances, and a wine cooler, perfect for entertaining. Enjoy alfresco dining on your private terrace overlooking the gardens, pool, and shimmering Gulf waters. Few properties offer the luxury of stepping directly from your home into the sand or strolling a few steps to what often feels like your very own private pool. Seagate is celebrated for its meticulous grounds and exceptional amenities. Meandering pathways wind through lush tropical gardens, while dedicated storage for kayaks and paddle boards makes it easy to explore the turquoise Gulf. Relax under the palm-thatch huts, unwind in the spectacular resort-style pool and spa, or stay active in the state-of-the-art fitness center that rivals those in five-star hotels. The newly renovated club room provides an elegant gathering space for conversation, games, watching TV, or preparing meals in the chef’s kitchen. Perfectly positioned on the coveted south end of Longboat Key, Seagate offers unmatched access to St. Armands Circle and all of the island’s finest dining, shopping, and recreation. This is truly an extraordinary opportunity to own within one of Longboat Key’s most beloved and impeccably maintained beachfront communities.
Listing Agent: Ryan Heers (941-726-1703)
3040 GRAND BAY BLVD #234, LONGBOAT KEY, FL 34228
$1,250,000124 Days on yellowkey MLS ID: A4675109
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2550 Built: 1996Community: Grand Bay 2Condo
Remarks: Arrive by private elevator into this 2BR + den, 3.5BA residence offering 2,550 sq. ft. in Grand Bay. Wood floors run throughout the main living areas, leading to floor-to-ceiling sliders with views of the Harbourside Golf Course and Sarasota Bay. The covered terrace extends the living space and is well suited for enjoying daylight and coastal breezes. The living and dining areas are well proportioned for everyday living and entertaining, with a tray ceiling in the dining room. A den with custom built-ins is currently used as an office and sitting area and offers flexibility as a potential third bedroom. The kitchen features white cabinetry, stone countertops, tile backsplash and ample counter space, along with an eat-in area that opens to the outdoor living area. The primary suite enjoys floor-to-ceiling glass and a bath with a walk-in glass shower, soaking tub, distinctive tilework and separate water closets. The guest bedroom offers quiet community views. A powder bath and an in-residence laundry room add convenience. Grand Bay amenities include a staffed lobby, clubhouse, two pools and spas, fitness center with saunas and Har-Tru tennis courts. Bay Isles privileges include walking paths and membership to the private Bay Isles Beach Club with gated Gulf-front access on Longboat Key, parking, restrooms and shaded picnic areas. Optional membership to the Longboat Key Club provides access to championship golf courses, private beach club, marina, tennis facilities, fitness center, dining venues and a full-service spa.
Listing Agent: Bruce Myer (941-376-5311)
3010 GRAND BAY BLVD #493, LONGBOAT KEY, FL 34228
$1,879,000192 Days on yellowkey MLS ID: A4668143
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 2550 Built: 1999Community: Grand Bay 4Condo
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.
805 SPANISH DR N, LONGBOAT KEY, FL 34228
$399,00075 Days on yellowkey MLS ID: A4681118
3 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1405 Built: 1968Community: Spanish Main Yacht Club CondoVilla
Remarks: One or more photo(s) has been virtually staged. Enjoy the Longboat Key lifestyle in this beautifully renovated, standalone, 3-bedroom 2-bath home at an exceptionally low price. This villa has it all - water and marina views, a bright, modern open kitchen, new appliances, and an indoor laundry room. It is now ready for you to move in. The roof, A/C, and windows were replaced in 2015 and new doors were installed in 2026. Spanish Main's deeded access to Longboat Key's uncrowded beach is across Gulf of Mexico Drive, and the deep-water marina and kayak launch near your front door offers boat slips as available at a very low annual price. The clubhouse is being renovated, and the nearby heated pool is now available. Spanish Main Yacht Club, an over 55 community, is conveniently located near several restaurants, a lovely park, Town tennis, pickle-ball, dog park, fitness activities, and St. Armands Circle shops and restaurants. Let me show you what this beautiful, unique community has to offer!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Adrienne Scott (941-264-5266)
601 NORTON ST, LONGBOAT KEY, FL 34228
$1,649,00063 Days on yellowkey MLS ID: A4682110
4 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2956 Built: 1986Community: Sleepy Lagoon Park 2Single Family
Remarks: Under contract-accepting backup offers. PRICE REDUCTION! Coastal elegance meets relaxed island living in this beautifully renovated and fully furnished Key West–style waterfront retreat on Longboat Key. Offering boating, beach, and three bedrooms and three full baths, this thoughtfully designed home also features a private guest/in-law suite complete with its own full bath and kitchenette—ideal for extended stays or visiting family and friends. Step outside to your own tropical oasis, where a heated in-ground pool and expansive paver lanai create the perfect setting for alfresco entertaining. The well-protected canal frontage includes a private dock with boat lift, water, and electric, providing effortless access to Sarasota Bay, the Intracoastal Waterway, and the Gulf. Boating enthusiasts will appreciate the direct, easy navigation, while beach lovers will enjoy the nearby neighborhood beach access just a short stroll away. Inside, the open great room floor plan showcases plank wood flooring, a cozy fireplace, and an expansive Florida room overlooking the water. The well-appointed kitchen features gas cooking and generous workspace—perfect for the home chef. The spacious main-level primary suite offers a walk-in closet and private en-suite bath, while a separate guest bedroom and adjacent full bath provide comfort and privacy. On the ground level, the fully appointed in-law / guest suite opens directly to the pool and lanai area and includes a full bath and new kitchenette. A versatile bonus space offers endless possibilities—game room, fitness studio, hobby space, or additional lounge area. Recent improvements include a new roof, Florida room addition with impact windows, Hardie board siding, in-law / guest suite kitchenette cabinets and appliances, and more. Lush tropical landscaping, raised planting beds, a kayak launch, paver drive and walkways, privacy fencing, and a welcoming front porch complete the exterior appeal. Located in the friendly Norton Street neighborhood, residents enjoy a voluntary social homeowners association with regular gatherings—one of the many reasons this is considered one of the island’s most desirable year-round communities. Waterfront luxury. Easy boating. Close to the beach. 601 Norton is your opportunity to embrace the very best of island living.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Michael Seamon (941-586-1802)
775 LONGBOAT CLUB RD #807, LONGBOAT KEY, FL 34228
$2,295,000192 Days on yellowkey MLS ID: A4667077
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1842 Built: 1984Community: Beaches Of Longboat Key Ph-1Condo
Remarks: Welcome to Beaches of Longboat Key - Unit 807 From a morning stroll on the beach to twilight cocktails on your wrap around balcony watching the glittering lights of Sarasota over the bay, you will experience beauty all around. Longboat Key, a jewel in the crown of the Sarasota Coastline, has so much to share. This elegantly appointed home will not disappoint. Custom finishes are abundant throughout the 1,842 sq ft condominium, not to mention the breath-taking views from the over 300 sq ft wrap-around balcony. This gracious home offers generous living space, with sweeping views from every window. Upon entering 807, you are greeted to stunning engineered Brazilian Cherry Hardwood flooring that continues throughout the home. A Reme Halo Air Purification System keeps the air fresh and clean. All windows and sliders are Impact. Beautiful crown molding throughout. The custom kitchen created by Campbell’s Cabinetry, Quartzite countertops, SubZero 42” Side by Side Refrigerator Freezer, Wolf Steam Convection Oven, GE Monogram Induction Cooktop, Zephyr PISA range hood. Bosch Dishwasher, Blanco Silgranite Sink, Hansgrohe Faucet. Custom cabinetry can be found throughout this beautiful residence. Primary Bedroom Suite offers views, comfort and luxury. Two bedrooms, each with well-designed baths, custom touches are found everywhere. There is one assigned parking space assigned to the unit on the upper level, and there is ample parking on the lower level for your second vehicle. Beaches is a great community offering you every convenience: 24-hour Concierge, Heated pool & Spa, Fitness Room, Tennis Courts, Social Room, Catering Kitchen, direct Walkway access to the Beach and a Basement Storage area. This proactive community is hard at work completing several important and vital projects: Stack Pipelining throughout the building, Roof Replacement will take place later this year and Temporary Wind/Surge Barriers are being purchased to protect the main floor of the building. Morning, noon and night, there is always something wonderful to experience at Beaches on beautiful Longboat Key. Schedule you showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: David Stasney (941-705-8464)
100 SANDS POINT RD #223, LONGBOAT KEY, FL 34228
$1,150,00090 Days on yellowkey MLS ID: A4679103
0 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1941 Built: 1966Community: Sands PointCondo
Remarks: Phenomenal opportunity to purchase a newly renovated condo in the exclusive Sands Point community. Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, nestled inside the gates of the highly sought-after, Longboat Key Club. This stunning 1,941 sqft second floor residence underwent a complete transformation in 2022-2023, and the results are nothing short of spectacular. Step inside this bright second-floor residence and discover three bedrooms and two bathrooms designed with meticulous attention to detail. Classic plantation shutters grace each room, while new tile flooring flows seamlessly throughout. The primary bedroom features custom-organized closets, while the second guest room cleverly incorporates a Murphy bed—perfect for maximizing space without sacrificing style. This split bedroom concept allows for privacy for your family and friends. The third bedroom doubles as a versatile office, adapting effortlessly to your lifestyle needs. The kitchen will make any culinary enthusiast weak in the knees. High-end appliances including a Fisher and Paykel induction range, Kitchen Aid dishwasher, refrigerator, and bonus refrigerated drawers all shine in crisp white enamel against stunning Shaker cabinetry and gleaming quartz countertops. The expansive living room steals the show with a dramatic wall of windows, gorgeous built-in cabinetry, and a dazzling dining chandelier that ties everything together beautifully. Both bathrooms feature light, airy cabinetry with elegant tile work and convenient walk-in showers. Community amenities abound—enjoy the beach with private tiki's and lounge chairs, pool, spa, library, community room with full kitchen, marina access, kayak launch, and bicycle storage. Nearby attractions include Overlook Park and Mote marine for endless exploration opportunities. With in walking distance to well renowned St. Armand's Circle for shopping and dining experiences. The pristine white sandy beach and gentle Gulf waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Diane Smith (941-313-4957)
2600 HARBOURSIDE DR #L-03, LONGBOAT KEY, FL 34228
$375,000371 Days on yellowkey MLS ID: A4648812
Bed: Bath: 0.0 Built: 1985Community: Longboat Key Moorings MarinaDock-Rackominium
Remarks: Ask an L-dock boater, they will tell you its the best dock in the marina. Slip is near the seawall with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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 village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 63 LOA, usable beam is 23 ft at the head of the slip.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,700,00034 Days on yellowkey MLS ID: A4686539
Remarks: Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
3060 GRAND BAY BLVD #155, LONGBOAT KEY, FL 34228
$1,195,00027 Days on yellowkey MLS ID: A4685023
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2250 Built: 1994Community: Grand Bay 1Condo
Remarks: Framed by sweeping vistas that span the manicured Harbourside golf course, Sarasota Bay, and the distant city skyline, this 3BR/3.5BA residence in Grand Bay offers an exceptional vantage point that captivates from the moment you arrive. Positioned on the fifth floor, the perspective is both expansive and elevated, showcasing breathtaking panoramic views while maintaining a strong visual connection to the surrounding landscape. The living room is thoughtfully designed to highlight this remarkable setting, with a full wall of sliding glass doors opening to a balcony that extends the entire length of the residence. From this elevated perch, corner walls of glass draw the eye outward, creating a dramatic focal point where golf course, bay, and skyline converge in one uninterrupted panorama. High ceilings with crown molding and tile flooring provide a clean, timeless foundation throughout the main living areas. The kitchen offers generous space and functionality, featuring stone countertops, under-cabinet lighting, a center island, stainless steel appliances, a tray ceiling, and an adjacent dining area. Well laid out and highly functional, it also presents an excellent opportunity to personalize finishes and reflect your own design vision. A versatile bonus room with an enclosure feature adds flexibility, ideal for a private office, media room, or additional guest accommodations. The primary suite serves as a comfortable retreat, complete with direct terrace access and serene sunrise views over Sarasota Bay. The spacious bath includes dual vanities, a soaking tub, glass-enclosed shower, and a separate water closet. Additional conveniences include an in-residence laundry room and under-building parking. Residents of Grand Bay enjoy a refined, amenity-rich lifestyle, with access to a clubhouse, two pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Ownership also includes the privileges of Bay Isles, featuring gated entry, scenic walking paths, and membership to the private Bay Isles Beach Club. Large dogs are welcome.
655 LONGBOAT CLUB RD #1PH, LONGBOAT KEY, FL 34228
$5,250,00077 Days on yellowkey MLS ID: A4680593
1 Days Off yellowkey (back on 3/24/2026)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 3139 Built: 1995Community: Regent Place Ph 1Condo
Remarks: Under contract-accepting backup offers. It has been 20 years since a penthouse came to market at Regent Place on Longboat Key. Can you imagine the breathtaking views this elusive residence offers, spectacular sunsets over the Gulf and the twinkling lights of downtown Sarasota’s skyline? This extraordinary penthouse has been completely reimagined with coastal sophistication, featuring refined details meant to be experienced, not just seen. Designed by Anne Folsom Smith Interior Design and expertly completed by Ocean Builders, the renovation is timeless in style and function. Offering over 3,100 furnished square feet, the residence showcases 12-foot ceilings, electric storm shutters, private elevator access, a personal two-car garage and two expansive covered balconies, ideal for enjoying panoramic views in every direction. Every room reflects a custom, thoughtfully curated design, seamlessly blending luxury and livability. Highlights include a Crestron smart home system, Mr. Steam shower, Fisher & Paykel, Sub-Zero and Wolf appliances, Neff cabinetry, Hansgrohe fixtures, electric shades, and custom built-ins that beautifully define each space while maintaining an effortless flow throughout the home. This is a residence that must be experienced in person. Behind the gates of the Longboat Key Club, Regent Place is among the island’s exclusive luxury communities, with just 36 residences, ensuring exceptional privacy and premier amenities including a heated beachfront pool and spa, resident clubhouse and fitness center, on-site management and 24/7 security, over 500 feet of private beach frontage and in a pet-friendly community. Enjoy an unparalleled resort lifestyle with golf, tennis, spa services, fine dining and boating just outside your door. Moments away, St. Armands Circle and downtown Sarasota provide world-class shopping, dining and cultural experiences. This is a once-in-a-generation opportunity to own a spectacular penthouse residence. Schedule your private showing today.
Listing Agent: Jo Rutstein (941-587-9156)
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