Location: Longboat Key
Do Not Show Listings
2295 GULF OF MEXICO DR #23S, LONGBOAT KEY, FL 34228
$1,295,000186 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,812
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
3804 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228
$397,00031 Days on yellowkey MLS ID: TB8490120
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1133 Built: 1970 Tax: $3,764 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,764
Tax Year: 2025
Remarks: Welcome to your new slice of paradise at the Beach Harbor Club! This gem is located in 'B' building, closest to the Gulf of Mexico, and less than one-minute walk to pristine white sand beach ! "This bright two-bedroom, two-bathroom condo has been thoughtfully updated for 2025 with a brand-new HVAC system and water heater, giving you total peace of mind. Standing out as a unique residence that is 12.5% larger than front-facing units, this south-facing home is drenched in tons of natural light and features a modern open-concept kitchen and living room design. The chef’s kitchen is a true centerpiece, boasting a 14-foot-long center granite counter and custom cabinetry with soft-close drawers and doors. Throughout the entire home, you will find cool-to-the-touch 18-inch travertine tiles on all floors and Bahama shutters on every window, while the primary suite offers a spacious walk-in closet and beautiful views of the Gulf—vistas that can also be enjoyed right from the foyer. Designed for convenience with two separate entrance doors, this condo makes it easy to walk to the beach via your deeded access on the pristine sands of Longboat Key or launch a kayak into the bay right from the community docks. Between the heated pool, fitness center, and sunset views over the water, it feels like a year-round vacation. You’re perfectly placed mid-key, so you can easily bike over to Bayfront Park for a game of pickleball or a walk along the bay trails. With a covered carport, everything is set for you to just arrive and start enjoying the coastal lifestyle—Longboat living truly doesn't get better than this! Schedule your tour today! Come and visit this Beauty, this will not last long!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Sarah Wampler (941-209-0676)
1211 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$1,590,000180 Days on yellowkey MLS ID: A4669896
REDUCED by $85,000 (5.1%) on 04/19/2026
Bed: 2 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2100 Built: 1985 Tax: $14,792 (2025)Community: PromenadeSpa: YesCondo
Taxes:$14,792
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Rarely available north-side corner residence at The Promenade showcases panoramic views of the Gulf of Mexico, Sarasota Bay, white sandy beaches, and the sparkling city skyline. This beautifully designed 2,100 sq. ft. “E” floor plan features two bedrooms plus a den/3rd bedroom (with an en-suite full bath) and three bathrooms, with a spacious split layout that captures natural light and breathtaking vistas from every room. The expansive living and dining areas flow seamlessly to two private terraces—set your morning coffee down as you watch the sunrise over the bay, and end the day with a glass of wine while taking in the sunset over the Gulf. A stylish wet bar adds the perfect touch for entertaining. The kitchen is a showpiece, featuring 2022 installed Sub Zero refrigerator/freezer, GE Monogram stainless-steel induction cooktop and oven, ASCO dishwasher and GE Monogram microwave / convection oven combo, a white subway tile backsplash, quartz countertops, sleek contemporary white cabinetry, and an eat-in area overlooking the bay. Engineered white oak hardwood floors extend throughout, adding warmth and sophistication. The primary suite offers stunning Gulf views, built-in cabinetry, and two walk-in closets, while the guest suite enjoys downtown views and a private bath. The third bedroom/den opens to a terrace overlooking the Gulf. Includes one deeded parking space and access to resort-style amenities—concierge, 24-hour security, fitness center, an Olympic-size heated pool, four Har-Tru tennis courts, and more.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
597 SPANISH DR N #12, LONGBOAT KEY, FL 34228
$350,0005 Days on yellowkey MLS ID: A4690602
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1429 Built: 1968 Tax: $2,897 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,897
Remarks: Enjoy the Florida lifestyle in this beautifully renovated 2-bedroom + den, 2-bath villa in the highly desirable Spanish Main Yacht Club on Longboat Key. Offering 1,429 sq. ft. of move-in-ready living space, this home features ceramic tile flooring throughout, an open-concept living and dining area, and a bright Florida room ideal for relaxing or entertaining. The den includes a closet, making it perfect as a home office or optional third bedroom. This maintenance-free residence offers exceptional amenities including deeded beach access, shuffleboard courts, and a clubhouse with a library and social rooms. Boating enthusiasts will appreciate bay and harbor access along with an on-site marina. The vibrant 55+ community also features a heated pool and active social calendar. Practical conveniences include inside laundry and an attached carport. Pet-friendly (one pet up to 35 lbs), the home is ideally located minutes from St. Armands Circle and a short drive to Anna Maria Island. A rare opportunity to enjoy relaxed coastal living in one of Longboat Key’s most sought-after communities.
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
535 SANCTUARY DR #A603, LONGBOAT KEY, FL 34228
$2,999,00012 Days on yellowkey MLS ID: A4689260
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 1990Monthly Fee: $1,281 Tax: $33,878 (2025)Community: SanctuarySpa: YesCondo
Taxes:$33,878
Remarks: Welcome to refined coastal living at The Sanctuary—an exclusive gulf-side enclave tucked behind the gates of the Longboat Key Club. This beautifully updated 6th-floor residence offers 2BR plus den, 2.5BA, and over 2,375± sq. ft. of sophisticated interiors paired with sweeping wrap-around terraces that capture panoramic views of the Gulf of Mexico, the Links golf course, and the Sarasota skyline. Thoughtfully renovated with a designer’s eye, the residence showcases rich wood flooring, high-impact glass throughout, and light-filled living spaces that seamlessly connect indoors and out. The gourmet kitchen is both stylish and functional, featuring crisp cabinetry, solid-surface countertops, stainless appliances, and a center island ideal for casual dining or entertaining. The primary suite is a private retreat with terrace access, stunning Gulf views, a spacious walk-in closet, and a spa-inspired bath. Guests are comfortably accommodated in a separate suite, while the den offers flexibility for a home office or additional sleeping space. Residents enjoy a true resort lifestyle with private deeded beach access just steps away, 24-hour gated security, under-building parking, on-site management, heated pool and spa, Har-Tru tennis courts, and a fitness center. Ownership also places you within the coveted Longboat Key Club, with world-class golf, tennis, and beachfront amenities. Perfectly positioned on the south end of Longboat Key, you’re just minutes from the renowned shopping, dining, and social scene of St. Armands Circle, along with the vibrant arts, culture, and waterfront restaurants of downtown Sarasota. For those seeking a luxury Gulf Coast lifestyle defined by elegance, privacy, and activity, this exceptional residence delivers. Schedule your private showing today and experience The Sanctuary at Longboat Key firsthand.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
1211 GULF OF MEXICO DR #610, LONGBOAT KEY, FL 34228
$1,395,00068 Days on yellowkey MLS ID: A4682918
5 Days Off yellowkey (back on 4/21/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1827 Built: 1985 Tax: $14,561 (2025)Community: PromenadeSpa: YesCondo
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 Agent: Roger Pettingell (941-387-1840)
4725 GULF OF MEXICO DR #314, LONGBOAT KEY, FL 34228
$774,900141 Days on yellowkey MLS ID: A4673798
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1104 Built: 1974 Tax: $10,125 (2024)Community: Sand CayCondo
Taxes:$10,125
Remarks: Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A well-established vacation rental with a strong income history, this property is an ideal opportunity for both personal enjoyment and investment. Nestled within an intimate beachfront community offering 340 feet of pristine Gulf frontage, Sand Cay provides an exceptional resort-style experience. Residents and guests enjoy first-class amenities including tennis courts, shuffleboard, a heated pool, basketball area, barbecue stations, a full-time on-site manager, and a convenient in-house rental program. Perfectly located, the resort is just minutes from the boutique shops and fine dining of St. Armands Circle and the vibrant arts and cultural attractions of downtown Sarasota. Light and bright, this third-floor garden-view condo is ideally situated between the pool and the beach. The inviting floor plan features two bedrooms, two bathrooms, a spacious living and dining area, an updated and fully equipped kitchen, a cozy den/office nook, and a private balcony with an awning—ideal for morning coffee or unwinding after a day by the Gulf. Your slice of Longboat Key paradise awaits. Schedule your showing today.
Listing Agent: Michael Albano, Pa (941-993-9571)
825 BAYPORT WAY #825, LONGBOAT KEY, FL 34228
$699,00085 Days on yellowkey MLS ID: A4680533
0 Days Off yellowkey (back on 4/21/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1981 Tax: $8,133 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$8,133
Remarks: Under contract-accepting backup offers. Mid Key on Longboat Key, 825 Bayport Way offers 1,601 square feet of living with 2 bedrooms and 2 bathrooms in an active bayfront community. A great room design with split bedrooms. The Florida room with access to the private outdoor terrace has tremendous views...especially for a nature lover. Unit is being offered turnkey furnished… also can be sold unfurnished. Enjoy beautiful bay views and the ultimate Florida lifestyle with the beach just steps away, easy access to Longboat Key’s soft white sands and stunning Gulf sunsets. The residence is designed for comfort and ease, ideal as a full-time home or a serene coastal retreat. The Bayport community enhances the experience with a heated swimming pool, tennis courts, pickleball courts, bocce ball, kayak storage, deeded beach access with umbrellas and chairs, and even scenic walking paths that wind through lush, well-maintained grounds. Whether you’re paddling on the bay, strolling by the water, or enjoying quiet mornings at home watching the sunrise, this property captures the essence of island Located in the heart of Longboat Key. This bayfront condo offers an exceptional opportunity to enjoy the best of Florida’s Gulf Coast lifestyle. Just moments from dining and cultural attractions of Longboat Key and nearby Sarasota, the location blends privacy with convenience. The residence invites relaxed coastal living, whether you’re entertaining guests, enjoying peaceful mornings, or embracing an active outdoor lifestyle. This is a rare chance to own in one of Longboat Key’s most desirable areas, where timeless architecture meets everyday life.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Tammy Garner (941-374-4161)
6701 GULF OF MEXICO DR #332, LONGBOAT KEY, FL 34228
$795,00018 Days on yellowkey MLS ID: A4689175
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 990 Built: 1971 Tax: $3,403 (2025)Community: Whitney Beach IiiCondo
Taxes:$3,403
Remarks: Finally, you have the opportunity to own your own "Walk-Out", Gulf Front, Beach Condo. Tucked just behind a beach grass sand dune and situated on a grassy knoll, this unit is perfectly positioned to benefit from refreshing sea breezes while offering spectacular sunset views. This rare one-bedroom condo has been completely remodeled and now features a unique two-bathroom floorplan. Remodeled Interior and Modern Upgrades: The spacious living area boasts premium appliances and upgraded stone countertops on new cabinetry within a newly designed open kitchen. Updates abound throughout the unit: new hurricane impact resistant sliding doors and a front window, along with modern bathrooms. The property is being sold turn-key—everything stays, making it a seamless move-in experience. Step inside and discover a bright, inviting interior with an open, light-filled layout designed to maximize both space and natural beauty. Large glass sliders connect the interior to the outdoors, bathing the kitchen and living area in sunlight and blending innovative functionality with coastal charm. The thoughtfully designed bedroom and bathrooms provide serene retreats, perfectly balancing comfort and style. Private Outdoor Oasis: The unique ground floor “Whitney Beach Gulfside” floorplan offers both a front privacy-fenced enclosed patio—ideal for alfresco dining or beachfront gardening—and a rear open patio for relaxation. Whether enjoying a quiet morning coffee or an evening cocktail, the gentle sea breeze creates the perfect setting for unwinding. Resort-Style Community Amenities: Enhance your lifestyle with a range of well-maintained community amenities, including a sparkling pool, tennis courts, shuffleboard, beach chairs, boat slips available for lease, and a tranquil pavilion by the bayou for water enthusiasts. Unmatched Location and Lifestyle: Experience the best of coastal living on Longboat Key. Whitney Beach is located on the quiet, northern end of Longboat Key, close to fantastic restaurants, shops, and shopping—just steps away, an easy bike ride, or a short drive to visit St Armands Circle. This condo combines a highly desirable location with the privacy and comfort of a casual beachfront lifestyle—perfect for year-round living, a seasonal retreat, or a smart investment. With one-month minimum rentals allowed up to 12 times per year, the property offers excellent investment potential. BONUS: the community features two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, ensuring a NO SURPRISE experience. Discover Longboat Key: Enjoy the finest Longboat Key has to offer, where luxury meets laid-back coastal charm. Schedule your private tour today!
Listing Agent: Faye Doyle (941-504-7496)
1965 GULF OF MEXICO DR #G5-303, LONGBOAT KEY, FL 34228
$635,000135 Days on yellowkey MLS ID: A4674747
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 933 Built: 1977 Tax: $6,230 (2024)Community: Seaplace IiiCondo
Taxes:$6,230
Remarks: Beachfront condo for sale renovated in coastal style. Available in the sought-after Seaplace community on Longboat Key. Ideally designed with an open floor plan, this residence is positioned to capture breathtaking views of the Gulf, offering stunning vistas of shimmering turquoise waters, its pristine sand beach and lush tropical landscaping. Turnkey furnished. This beach condo features an updated and open kitchen with granite countertops and stainless steel appliances, creating an inviting space for cooking and entertaining. Both bedrooms are impressively spacious, and the primary suite has a generous walk-in closet and a lovely waterfront view. Enjoy your morning coffee or sunsets from the screened-in lanai, where the sweeping Gulf views serve as your daily backdrop. For added convenience, the condominium includes a separate storage unit ideal for bikes, beach gear and more. Residents of Seaplace enjoy one of the most desired settings on Longboat Key. Spanning 43 acres along the Gulf, this private, gated community offers a half mile of pristine beachfront with complimentary beach chairs and umbrellas. Resort-style amenities include two heated swimming pools, two spas, a kiddie pool and a playground. The recently remodeled clubhouse features a fitness center, sauna, library, large kitchen, enhanced audio/visual capabilities, and a spacious Gulf-front patio equipped with multiple grills. Additional amenities include three Har-Tru tennis courts and a scenic one-mile walking trail. Enjoy the best social community with gatherings at sunset and happy hour. Whether you’re seeking a tranquil coastal retreat or a vibrant, amenity-rich social community, this Seaplace condominium delivers the best of Longboat Key living. Short drive to Publix/CVS and to easy to drive to get to downtown Sarasota and the airport.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Judy Mitchell (941-275-6838)
605 SUTTON PL #201, LONGBOAT KEY, FL 34228
$619,00030 Days on yellowkey MLS ID: A4687586
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1148 Built: 1973 Tax: $6,756 (2025)Community: Sutton PlaceCondo
Taxes:$6,756
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: This is the one you have been waiting for!! INCREDIBLE UNOBSTRUCTED BAY VIEWS & BREATHTAKING SUNRISES from this light-filled CORNER unit in the beach-to-bay community of Sutton Place. Enjoy stunning vistas from nearly every room through impact windows and doors! Meticulously maintained and beautifully renovated, this spacious two-bedroom, two-bath coastal retreat is truly exceptional. The thoughtfully designed open concept chef’s kitchen with premium cabinetry, plentiful storage, and Cambria quartz countertops seamlessly connects to the expansive living area through a custom dining island with wraparound seating. Plantation shutters throughout the kitchen and living area add to the coastal island feel. The enclosed lanai, featuring walls of glass that span along the rear of the unit, provides an ideal setting for morning coffee, evening relaxation, remote work, or accommodating additional guests. The spacious primary and secondary bedrooms provide exceptional views, each with direct access to the lanai through impact-rated sliding doors. The serene primary bedroom boasts a generous walk-in closet fitted with a custom organizer and an elegantly renovated bathroom with a walk-in shower, complete with a linen closet. The secondary bedroom offers ample storage with a double closet, also fitted with custom organizers. The adjacent guest bath has been tastefully renovated. Parking is easy with a covered, assigned space in a convenient location, plus plenty of overflow and guest parking. While the stairs are easily accessible; there is also an elevator for added convenience. The in-building storage unit provides extra space for any additional storage needs. Sutton Place offers a wide range of amenities, including two heated swimming pools, a community clubhouse, marina facilities with boat slips (current wait list but only $300 annually!!), kayak storage equipped with electric launch, a fish cleaning station, designated grilling areas, car wash stations, and deeded beach access with private beach pavilion featuring storage lockers, showers, and restrooms. The community successfully endured the recent storms, experiencing minimal overall damage and no impact to any individual units. With its exceptional location, unmatched views, and wonderful amenities, this property is an opportunity not to be missed! Schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Melissa Rodocker (703-969-2345)
3240 GULF OF MEXICO DR #B402, LONGBOAT KEY, FL 34228
$895,00044 Days on yellowkey MLS ID: A4686024
REDUCED by $10,000 (1.1%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1505 Built: 1975 Tax: $8,208 (2025)Community: PortobelloSpa: NoCondo
Taxes:$8,208
Remarks: TURNKEY Furnished Portobello condo with Deeded Beach Access! TWO Balconies with Sunsets AND Sunrises included! Enjoy Beach and Bayou water access! Rarely available end unit with two balconies and lots of privacy and natural lighting. The front open balcony has unobstructed Gulf views whilst the rear balcony is glassed in with sliders/screens and faces the Bayou. This 4th Floor condo has elevator access, 1 owners storage locker, ample in unit storage and 1 assigned parking space. Condo fee includes Water, Sewer, Trash, Cable/Internet, Pest Control, on site Maintenance and Exterior Insurance. Well established social community with Community Pool, Clubhouse, Tennis Courts, Kayak storage/launch, Fishing Pier, BBQ area and ELEVATED mature landscaping. This spacious floorplan is one of the larger floorpans in the community providing you with list and bright spaces, tons of closet space and even a bonus study/den area to use as you please! Stacked Washer/Dryer located near the hallway 2nd Bathroom which has been renovated. Beautifully upgraded Kitchen with high quality cabinetry and 4 storage closets for all your pantry, cleaning and large cooking items. The Primary Bedroom has the most wonderful private bayou water views! Attached en suite full bathroom with lots of counter space. Secondary bedroom has its own separate balcony entrance. This community is located a short drive away from Publix, CVS, banks, Post office, nail salons and Golfing! New development nearby is bringing more shopping and dining! Don't miss this opportunity to own in the sough after Portobello community!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Monica Desomma (202-427-4328)
2110 HARBOURSIDE DR #523, LONGBOAT KEY, FL 34228
$699,00060 Days on yellowkey MLS ID: A4682869
REDUCED by $26,000 (3.6%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988 Tax: $5,680 (2025)Community: Fairway BaySpa: NoCondo
Taxes:$5,680
Remarks: Experience elevated coastal living in Bay Isles at The Atrium, where this stunning 3-bedroom, 2-bath residence showcases breathtaking views of Sarasota Bay that truly steal the show. From the moment you step inside, you are welcomed by sweeping water views that stretch for miles, sparkling blue during the day and glowing with unforgettable sunset colors in the evening. The expansive private terrace serves as an extension of your living space, offering the perfect setting for morning coffee as boats drift by, sunset dinners, or simply relaxing while taking in the panoramic Bayfront scenery. The spacious primary suite is a serene retreat with direct terrace access, allowing you to wake up each morning to breathtaking water views, while the spa-like primary bath provides a peaceful escape designed for ultimate relaxation. Ideally located just minutes from St. Armands Circle and vibrant downtown Sarasota, you'll enjoy world-class dining, boutique shopping, and cultural attractions right at your fingertips. Residents of Bay Isles enjoy exclusive access to the private Bay Isles Beach Club, featuring a pristine Gulf-front beach, barbecue grills, volleyball, and covered picnic tables. The Atrium offers exceptional amenities including tennis and pickleball courts, a clubhouse, heated pool, fitness center, and on-site management. This is your opportunity to live in paradise on Longboat Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Caroline Mitchell (913-787-3131)
360 GULF OF MEXICO DR #333, LONGBOAT KEY, FL 34228
$1,795,000104 Days on yellowkey MLS ID: A4675387
REDUCED by $5,000 (0.3%) on 04/20/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2581 Built: 1992Monthly Fee: $50 Tax: $10,264 (2025)Community: Tangerine Bay ClubCondo
Taxes:$10,264
Remarks: Welcome to this rarely available corner penthouse with its stunning bayfront views artfully framed by the freshly landscaped tropical oasis surrounding the resort-style pool. Boasting nearly 2600 square feet of interior space on two levels, this serene sanctuary offers three terraces plus 3 bedrooms and 3.5 baths (3045 square feet in total). A private courtyard sets the stage for a gracious residence with a warm European feel that lives like a single family home. Relaxed open spaces beckon with soaring ceilings, extra windows in the kitchen and great room (available only in end units), and a gas fireplace. The kitchen features a morning room with built-in desk and an aquarium window over the sink. Sliding glass doors seamlessly connect indoor and outdoor spaces. Mahogany double doors open into the primary suite with its patio access overlooking the bay and lush landscaping, volume ceilings, acacia wood flooring, walk-in and built-in closets and recently renovated luxurious bath. An additional guest bedroom (currently used as a den) with ensuite bath, laundry room and powder room complete the first level. On the second level a spacious third bedroom, office with built-in desk, shelving and storage, and full bath provide additional accommodations for family and friends. The home offers impact windows, plus storm shutters on larger windows for added protection. Enjoy the resort style amenities of Tangerine Bay Club, including a lagoon pool with waterfalls, lap lane and spa, day dock, fishing, kayak launch, tennis and pickleball courts, fitness center, clubhouse, walking paths and tropical landscaping. An oversized garage provides ample space for sports equipment and storage. Owners may join the newly remodeled Bay Isles Beach Club providing access to the Gulf of Mexico for a modest annual fee. Located on Longboat's south end, this gated community is just minutes from the new St. Regis resort and St. Armand's Circle with its shops and fine dining. A short drive over the Ringling Bridge brings the vibrant culture and renowned arts of downtown Sarasota. Optional membership in the Longboat Key Club across the street from TBC offers 45 holes of award winning golf, fine dining and a marina. Come see why Tangerine Bay Club is one of Longboat's most sought after communities and why Forbes named Longboat Key one of the top 25 destinations in 2025.
Listing Agent: Sherry Dominick (203-605-9582)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000170 Days on yellowkey MLS ID: A4670624
REDUCED by $90,000 (9.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $5,337 (2024)Community: Club LongboatSpa: YesCondo
Taxes:$5,337
Remarks: One or more photo(s) has been virtually staged. Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of pristine Gulf frontage, this home immerses you in the beauty and serenity of coastal living. Beautiful engineered white oak wood floors flow throughout the open, sun-filled living space, which seamlessly extends to your private balcony’s, the perfect spot to enjoy the tranquil sound of the waves and stunning sunsets. The updated kitchen features stone countertops, white cabinetry, and has been opened up to create a larger, more connected floor plan ideal for entertaining. The primary suite is a private sanctuary, boasting a remodeled marble bath with high-end fixtures and a spa-like ambiance. The guest suite provides equal comfort and privacy, featuring a beautifully appointed travertine-floored bathroom. A custom wall of California closets offers exceptional storage and style. The Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, eight professional har-tru tennis courts, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat is a pet-friendly community allowing up to two pets with fees that include exterior maintenance and insurance, cable, water, sewer and trash. Perfect as a full-time residence or an income-producing rental, with one-month minimum leases permitted up to 12 times per year. Only a short drive to many fine restaurants, boutiques, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Schedule your showing today and make resort style living a reality.
Listing Agent: Ryan Heers (941-726-1703)
545 SANCTUARY DR #B204, LONGBOAT KEY, FL 34228
$2,799,000185 Days on yellowkey MLS ID: A4667288
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3115 Built: 1991 Tax: $19,659 (2025)Community: Sanctuary IiiSpa: YesCondo
Taxes:$19,659
Remarks: Prepare to be wowed by the direct turquoise Gulf views from the oversized wraparound terrace, main living areas and primary bedroom. The chef’s kitchen is open to the main living area and offers state-of-the-art JennAir stainless steel appliances complete with built-in convection and steam ovens, oversized center island, wine refrigeration with storage and breakfast area. The massive primary suite showcases floor to ceiling windows with the same big Gulf views, access to the terrace, garden tub with separate shower and two walk-in closets. The main guest bedroom is ensuite with its own private terrace access and another walk-in closet. The 3rd bedroom is being used as a den with French doors opening to the living room, its own ensuite full bath with shower and dazzling Gulf views. Other bonus rooms include a laundry room located conveniently off the kitchen with sink, and an office nook with built-ins adjacent to the foyer. This residence comes with TWO under building parking spaces and a separate storage locker. Located behind the prestigious gates of The Longboat Key Club on the desirable South end of Longboat Key, owners will enjoy being minutes from the fine dining and shopping on St. Armands Circle in addition to the close proximity to Southwest Florida’s cultural hub of downtown Sarasota. At the Sanctuary, you will be part of 18 incredible beachfront acres with trails, an Olympic sized heated pool and spa, lighted tennis courts, a fitness center, onsite management, 24-hour manned security gate and a club house with planned activities. Become a member of the Longboat Key Club and partake in the superior golf courses, 6 private restaurants, spa and wellness center and other AAA four-diamond beach resort offerings. Roof replaced in 2023, Elevators modernized in 2022, and pool decking replaced in 2024. Building passed the Milestone Structural Integrity Inspection.
Listing Agent: Ian Addy, Pa (941-961-8850)
5320 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,150,000204 Days on yellowkey MLS ID: A4666843
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1323 Built: 1981Monthly Fee: $1,483 Tax: $11,774 (2024)Community: Longboat LandingCondo
Taxes:$11,774
Remarks: Rarely Available at Longboat Landing! This 3-bedroom, 2-bath second-floor condo offers the ultimate in coastal living with only 9 total units/owners in the entire community—providing privacy, exclusivity, and a boutique feel. Enjoy full Sarasota Bay views from your living room, with the added peace of mind of being on the second floor (no flood concerns). Inside, you’ll find engineered hardwood floors, a granite countertop kitchen, and hurricane impact windows that fill the space with light and frame the water beyond. The spacious primary suite offers a private retreat, while two additional bedrooms provide room for guests, a home office, or flex space. Outside, embrace the Longboat Key lifestyle with a boat dock slip, fishing pier, and community amenities designed for waterfront enjoyment. Perfectly located on Gulf of Mexico Drive, just minutes from island dining, boutique shopping, and the world-renowned beaches of Longboat Key. Rarely available. Bayfront views. Exclusive 9-owner community. This one is not to be missed!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Schuyler Burke (907-223-8161)
210 SANDS POINT RD #2405, LONGBOAT KEY, FL 34228
$1,100,000233 Days on yellowkey MLS ID: A4664039
REDUCED by $50,000 (4.3%) on 04/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 650 Built: 1982 Tax: $9,827 (2024)Community: Inn On The Beach Ph ICondo
Taxes:$9,827
Remarks: Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suite at Inn on the Beach offers a unique opportunity to own within the prestigious Longboat Key Club Resort. Spanning 650 sq. ft., this residence provides both convenience and privacy, with an expansive covered terrace offering peaceful Gulf views while keeping you close to every amenity. Completely renovated and meticulously styled, the interior pairs warm wood accents with neutral tones, complemented by faux wood tile floors flowing throughout. Dual sliders frame shimmering Gulf waters and invite natural light into the living space. The kitchen is a standout, with stone countertops, harmonizing cabinetry with glass panel accents and a colorful tile backsplash that adds just the right touch of vibrancy. Off the bedroom space, a beautifully updated bath features all-white cabinetry, a separate water closet and a glass walk-in shower with striking tilework. For added ease, in-unit laundry utilities are included. This unit participates in the Resort Rental Program and has a healthy rental history, with nightly rentals allowed, making it both an enjoyable retreat and a strong investment. As an owner, you’ll have access to the exclusive amenities of the 410-acre Longboat Key Club, including 45 holes of championship golf, 20 Har-Tru tennis courts at the award-winning Tennis Gardens, a full-service marina, private Gulf-front beach with umbrellas and attendant service, a world-class fitness and wellness center, spa and five private dining options. Recently renovated guest services, dining areas, and resort amenities have elevated the experience even further, earning accolades such as the AAA Four-Diamond Award and recognition from Condé Nast Traveler as a Top Florida Resort.
600 SUTTON PL #104B, LONGBOAT KEY, FL 34228
$545,000405 Days on yellowkey MLS ID: A4644920
REDUCED by $25,000 (4.4%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1973 Tax: $6,737 (2024)Community: Sutton PlaceCondo
Taxes:$6,737
Remarks: Incredible FULL BAY VIEW! This tranquil and beautifully renovated island retreat located in the beach to bay community of Sutton Place offers that and so much more. This 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous, remodeled kitchen is open to the living/dining area across an expanse of granite that includes a custom made dining table with lots of storage underneath and seating all around! Porcelain tile flooring makes the journey from one room to another a seamless and beautiful transition. These smart owners have converted the lanai into finished square footage and it is the perfect spot to enjoy a morning coffee or an evening beverage while watching the fish jump or the birds fly by. They also upgraded to IMPACT RESISTANT SLIDING DOORS AND WINDOWS throughout. The Primary bedroom has this same gorgeous view and a renovated ensuite bath. The once walk-in closet was converted to a small office space, (which could easily be changed back) but it’s current use is rather genius. When guests are not in town, the 2nd bedroom is another tranquil space to enjoy. Did I mention this is a 2 pets friendly community?! Sutton Place also offers its own PRIVATE BEACH CLUB and includes an abundance of amenities including 2 pools, a clubhouse, and an onsite marina with slips for a nominal fee of only $300 per year. The community recently completed a number of updates including repainting, reroofing and passing the milestone inspection and securing a 10 year certification. This owner has paid for all of those upgrades in full. The unit is being offered furnished with exceptions. Here you will find a remarkable quality of laid-back island life but if you're ready for more, enjoy the multitude of restaurants, shopping and the cultural mecca of downtown Sarasota, all within a short drive away.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4835 GULF OF MEXICO DR #302B, LONGBOAT KEY, FL 34228
$849,900419 Days on yellowkey MLS ID: A4642701
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Monthly Fee: $1,858 Tax: $11,313 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$11,313
Remarks: One or more photo(s) has been virtually staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors open to a private balcony with breathtaking ocean views. Both bedrooms feature spacious walk-in closets, ceiling fans, while both bathrooms have been fully remodeled with modern, high-end finishes and Toto washlet toilets. The newly updated kitchen boasts a sleek induction stove with a vented range hood, perfect for cooking with a view. New AC, LED lighting, and brand-new impact sliding doors enhance comfort and efficiency. Beyond your private oasis, take advantage of resort-style amenities, including two Gulf-front heated pools unique to the Westchester, Elevators, tennis courts, and direct beach access. Plus, you’re conveniently located just minutes from Publix, top-rated restaurants, and boutique shopping. Enjoy short rides to the vibrant St. Armands Circle and downtown Sarasota, where world-class dining, entertainment, and cultural attractions await. This is coastal luxury at its finest—don’t miss your chance to own a piece of paradise!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Donna Wrobel (941-518-7950)
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