Location: Longboat Key
Do Not Show Listings
1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$975,000214 Days on yellowkey MLS ID: A4674194
REDUCED by $25,000 (2.5%) on 06/25/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1707 Built: 1983 Tax: $11,336 (2025)Community: Players Club IvCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,336
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Mairead Smialek (847-334-4848)
2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$2,050,00027 Days on yellowkey MLS ID: A4697202
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3083 Built: 1990 Tax: $20,065 (2025)Community: Marina BayCondo
Taxes:$20,065
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome home to this corner 3 bed/3.5 residence with sweeping southeast bay and city views at Marina Bay behind the Bay Isles gates on Longboat Key. This showstopping residence has been recently renovated with designer inspired flooring, fixtures and thoughtful details throughout. The kitchen and dining rooms are positioned to capture direct views of Sarasota Bay while offering every convenience including a full wet bar area with wine refrigeration, custom cabinetry, breakfast bar, cabinet pantry and large laundry room with another closet pantry. The expansive living area features incredible wall space for works of art with natural light from the floor to ceiling sliders surrounding the wraparound screen terrace which frames the city skyline and Sarasota Bay. The primary suite has its own private wing and boasts a large shower with multiple shower heads, floating vanity, designer stone tilework, two large walk-in closets and a peaceful bedroom sanctuary with access to the west terrace and tranquil sunset skies. Both guest bedrooms are ensuite with ample closet space (one walk-in and one built-in) and recently renovated bathrooms. Other highlights include hurricane shutters, plantation shutters, automatic shades in the main living area, an under-building parking space, semi-private elevator and membership to the Bay Isles Beach Club on the Gulf. The Beach Club is a private, gated retreat for Bay Isles residents offering a large outdoor pavilion, tropical cabanas, grills and picnic facilities, private showers and restrooms. Marina Bay is a pet friendly community with on-site management, heated pool & spa, gas grill area, fitness room, tennis and pickleball courts. Located nearby the Longboat Key Club Marina, Publix, CVS, Post Office and minutes from St Armands and the cultural hub of downtown Sarasota. Get ready to start your Longboat Life today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
230 SANDS POINT RD #3205, LONGBOAT KEY, FL 34228
$996,000281 Days on yellowkey MLS ID: A4667440
REDUCED by $29,000 (2.8%) on 06/25/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 634 Built: 1982 Tax: $9,514 (2025)Community: Inn On The Beach Ph ICondo
Taxes:$9,514
Remarks: Spectacular Gulf and Sunset views are enjoyed from this west facing Junior Suite in Building 3. The direct beach view through the swaying palms perfectly encompasses the resort lifestyle and the vision guests have of tropical landscapes when making reservations. This completely renovated residence is currently in the hotel program and reported healthy income in 2023 and 2024. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, Spa/Wellness Center, white sand beach with umbrellas and waitstaff and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start your Longboat Life today!
775 LONGBOAT CLUB RD #401, LONGBOAT KEY, FL 34228
$1,595,000135 Days on yellowkey MLS ID: A4681439
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1510 Built: 1984 Tax: $13,823 (2025)Community: Beaches Of Longboat Key Ph-1Spa: YesCondo
Taxes:$13,823
Remarks: Discover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gated entrance of the Longboat Key Club, The Beaches offers an unparalleled Gulf-front retreat on one of Florida's most exclusive barrier islands. This stunning 4th-floor, 2-bedroom/2-bath residence boasts direct western exposure, delivering breathtaking, forever Gulf of Mexico views and spectacular sunsets that paint the sky in vibrant hues every evening. Step inside to find stylish, move-in-ready finishes, including brand-new porcelain tile flooring throughout the living areas and elegant marble in both bathrooms. The updated kitchen shines with fresh cabinetry, a new GE Profile refrigerator, and dishwasher—perfect for effortless entertaining or quiet evenings at home. The spacious living room and both bedrooms feature impact-resistant sliders that open to a private balcony, seamlessly blending indoor comfort with the soothing sights and sounds of the beach and surf just steps away. Residents enjoy an exceptional array of resort-style amenities: 24-hour concierge service for added security and convenience, Gulfside heated pool and spa, Modern fitness center, Two Har-Tru tennis courts, Social room with a full catering kitchen, Direct beach walkway with complimentary beach chairs (and often umbrellas) provided. Additional perks include two assigned parking spaces in the secure garage and a dedicated storage unit. Priced to impress in this highly sought-after community, this turnkey condo combines modern luxury, prime beachfront access, and the prestige of Longboat Key Club living—without requiring club membership. Opportunities like this rarely last long on Longboat Key. Don't miss your chance to own a slice of paradise—schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Larry Brzostek (941-993-3125)
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,850,000165 Days on yellowkey MLS ID: A4680080
1 Days Off yellowkey (back on 6/24/2026)
REDUCED by $149,950 (7.5%) on 06/10/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $9,861 (2025)Community: PierreCondo
Taxes:$9,861
Remarks: Under contract-accepting backup offers. Welcome to The Pierre, a distinguished Gulf-front address behind the private gates of the Longboat Key Club, offering a rare blend of refined coastal living, privacy, and world-class resort lifestyle appeal for discerning buyers from around the globe. Located on the seventh floor, Residence 707 showcases spectacular sunset skies over the Gulf of Mexico, complemented by peaceful bay and city vistas, creating a dynamic panorama from sunrise through evening. Expansive windows fill the interiors with natural light while framing the natural beauty of Longboat Key’s shoreline and Sarasota Bay. Thoughtfully designed for both relaxed living and gracious entertaining, the residence offers generous living spaces and a seamless indoor-outdoor connection. The floor plan includes two ensuite bedrooms and a flexible third bedroom with sliding retractable wall, three full baths, and spacious living and dining areas—each with direct access to the residence’s gracious balconies. Residents of The Pierre enjoy an exceptional array of amenities, including direct private beach access, a beachfront pool, spa, fitness center,, tennis courts, a newly renovated lobby, club gathering room, meeting room and 24-hour guard security. Private guest suites are also available for visiting family and guests on a nominal rental basis. Ownership is further enhanced by secure garage parking, a private secured storage area, and onsite professional management, providing ease and confidence for both year-round and seasonal owners. Beyond the residence, membership opportunities at the renowned Longboat Key Club provide access to a celebrated resort lifestyle, featuring championship golf courses, world-class tennis, spa and wellness facilities, multiple dining venues, beach services, and an active social calendar (membership subject to application and availability). Perfectly situated near St. Armands Circle and downtown Sarasota’s cultural attractions, Residence 707 represents a rare opportunity to own within one of Longboat Key’s most prestigious waterfront communities—where international sophistication, panoramic views, and a coveted club lifestyle converge in one extraordinary coastal setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
100 SANDS POINT RD #324, LONGBOAT KEY, FL 34228
$980,000795 Days on yellowkey MLS ID: A4609759
INCREASED by $90,000 (10.1%) on 06/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1941 Built: 1966Monthly Fee: $1,614 Tax: $11,167 (2023)Community: Sands PointSpa: YesCondo
Taxes:$11,167
High School: Sarasota High
Tax Year: 2023
Remarks: BACK on the market after beautiful renovations!! Unit is impeccably maintained. It has a new air conditioner, roof and upgraded insulation. It is being offered below appraised value! Sands Point is the most remarkable and unique complex on Longboat Key. Built in 1966, the building is a magnificent example of mid-century modern architecture. The complex faces directly onto New Pass, and the outdoor pool and patio have both privacy and spectacular views. The center of the unit is a large great room that features a wall of windows and a view of lush Florida greenery, the boat dock and the navigable inlet which leads to the Gulf of Mexico. Kitchen and bathrooms are renovated. Furniture and furnishings are included in the sale. Windows have been upgraded to the highest level available. Each unit comes with a small storage locker near the boat docks and covered parking. There are boat docks on the premises, approximately 30 ft., that can be rented depending on availability. Management has updated status and detailed information. Sands Point is located adjacent to The Resort at Longboat Key Club with its amenities of golf, health spa, lodging and a restaurant. Nearby is the famous St. Armand's Circle that offers elegant or casual dining and entertainment. Seasonal rental is a huge draw for this property. It may be rented once a year for a minimum of one month.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Carolyn Clark, Pa (941-685-6131)
4825 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$799,000286 Days on yellowkey MLS ID: A4667044
REDUCED by $40,900 (4.9%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $11,897 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$11,897
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
546 SPANISH DR S, LONGBOAT KEY, FL 34228
$499,00043 Days on yellowkey MLS ID: A4694824
REDUCED by $10,000 (2.0%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1241 Built: 1966 Tax: $2,488 (2025)Community: Spanish Main Yacht Club CondoSpa: NoCondo
Taxes:$2,488
Remarks: The lifestyle stays premium. The price just got friendlier. Tucked within the waterfront community of Spanish Main Yacht Club on the north end of Longboat Key, this fully renovated detached villa offers a timeless coastal flair just steps from the beach. A true hidden gem and slice of paradise, residents enjoy private deeded beach access to the Gulf of America, a deep water marina with affordable boat slips, and the ultimate boating lifestyle with easy access to waterfront restaurants and open waters. This light and bright 2-bedroom, 2-bath residence is being offered turnkey furnished. Featuring an open floorplan with luxury vinyl plank flooring, impact windows and doors, custom window shades throughout, and a spacious Florida room ideal for additional living or entertaining space. The beautifully updated kitchen showcases quartz countertops, stainless steel appliances, abundant custom cabinetry with soft-close drawers, and a large seating island perfect for gathering. Additional highlights include an interior laundry room with stackable washer and dryer, water softener system, stone paver patio, covered parking, and private driveway. Spanish Main Yacht Club is a vibrant and active 55+ community offering a heated waterfront pool, shuffleboard, social events, pet-friendly policies, maintenance-free living, and one of the most desirable 40-slip marinas on Longboat Key. Ideally located just minutes from St. Armands Circle, Sarasota, and Anna Maria Island, this exceptional Longboat Key retreat is ready for immediate enjoyment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Jackie Griese (941-718-0045)
6700 GULF OF MEXICO DR #143, LONGBOAT KEY, FL 34228
$410,00074 Days on yellowkey MLS ID: A4692139
REDUCED by $15,000 (3.5%) on 06/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 936 Built: 1969 Tax: $2,215 (2025)Community: Whitney BeachCondo
Taxes:$2,215
Remarks: Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story condo is being offered turnkey furnished, making it completely move-in ready—just bring your suitcase and start enjoying island life. Inside, the bright living room showcases peaceful water views bringing the beauty of marine life right to your window. The kitchen features stainless steel appliances and coastal-inspired design. The home offers a relaxed, airy feel perfect for full-time living, a seasonal getaway, or an investment property. This pet-friendly and rental-friendly community is vibrant and social, offering an unmatched waterfront lifestyle. Residents enjoy private beach access, two pools, tennis and shuffleboard courts, a fitness center, and kayak launch and storage. Boating and fishing enthusiasts will appreciate the boat slips and fishing dock, while outdoor living is elevated with grill stations, picnic areas, and complimentary beach chairs. Whether you are searching for a relaxing coastal escape or an active waterfront lifestyle, this exceptional Longboat Key condo delivers the very best of Florida living with breathtaking water views, abundant amenities, and endless opportunities to enjoy the beauty of marine life and island living!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Brooke Moran (941-705-3351)
528 FOREST WAY, LONGBOAT KEY, FL 34228
$585,00038 Days on yellowkey MLS ID: A4695863
3 Days Off yellowkey (back on 6/22/2026)
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1440 Built: 1989Monthly Fee: $945 Tax: $3,072 (2025)Community: Cedars East Sec 2Condo
Taxes:$3,072
Remarks: Under contract-accepting backup offers. Elevated, renovated, fully furnished, pet friendly, close to the beach AND a short term rental opportunity on Longboat Key?! This is the one you've been looking for! You don't have to be a tennis player to understand the value of this fabulous townhome in Cedars Tennis Club. This 2 bedroom, 2 and a half bath condo is the perfect island escape. Beautifully updated and furnished, all you’ll need to bring is your bathing suit and a toothbrush to start enjoying island life to the fullest. Add to it a short term two week rental policy, this could also be your perfect investment property. Current annual income has been around $50,000, but that also includes a lot of family enjoyment in between. New impact windows, a new roof, 2021 air conditioning units and a private garage make this condo even more appealing. Spend your days in the sun with just a short walk to the beach or the Bay. Enjoy the community swimming pool, with a fabulous tiki bar. Join the club to enjoy the fitness center and tennis privileges. Take a bike ride on 11 miles of bike paths down the island or a walk to Joan Durante Park. The cultural mecca of downtown Sarasota is just a short drive away. And don’t forget to make time to see the stunning evening sunsets. The Longboat Key lifestyle is waiting for you!
210 SANDS POINT RD #2402, LONGBOAT KEY, FL 34228
$999,90034 Days on yellowkey MLS ID: A4696591
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1982 Tax: $10,500 (2026)Community: Inn On The Beach Ph ISpa: YesCondo
Taxes:$10,500
Tax Year: 2026
Remarks: The Resort at Longboat Key Club – Gulf Front Condo-Hotel Investment Opportunity Best Priced Beachview Condo. Rxperience the best of coastal luxury and income-producing ownership at The Resort at Longboat Key Club. This beautifully renovated, turnkey one-bedroom Club Suite offers breathtaking direct views of the Gulf of Mexico, overlooking both the pristine beach and resort-style pool. Designed for effortless ownership, this exceptional residence is currently enrolled in the resort's rental program and professionally managed in partnership with Opal Hospitality, allowing owners to enjoy personal use while generating rental income.Whether you're seeking a vacation retreat, an investment property, or both, this Gulf-front suite delivers an unparalleled resort lifestyle. Ideally located just minutes from St. Armands Circle, you'll enjoy easy access to boutique shopping, exceptional restaurants, arts, culture, and all that Sarasota's Gulf Coast has. Recent renovations provide a fresh, modern coastal aesthetic, making this residence truly move-in ready. Don't miss this rare opportunity to own a piece of paradise in one of Florida's most sought-after luxury resort destinations. Enjoy the benefits of resort ownership, professional management, and spectacular Gulf views—all in one extraordinary property. Guests and owners alike enjoy world-class amenities, including: 45 holes of championship golf Award-winning tennis facilities Full-service marina Luxury spa and wellness services Fine dining and resort lounges Beachfront pool and private beach access Concierge and maid service
Listing is courtesy of: MY FLORIDA BROKER (941-932-2707)
Listing Agent: Patti Bosco (941-932-2707)
2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
$899,000137 Days on yellowkey MLS ID: A4683112
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $7,576 (2025)Community: Islander Club Of LongboatCondo
Taxes:$7,576
High School: Riverview High
Remarks: Welcome to The Islander Club — your turnkey getaway awaits! Step into coastal living with this beautifully updated residence offering effortless style and year-round relaxation. The open, sun-filled layout features tasteful luxury finishes and seamless access to a 38-foot terrace, perfect for unwinding after a day at the beach. Unit 54S has been thoughtfully upgraded throughout, showcasing wood flooring, an updated kitchen with stainless steel appliances, refreshed bathrooms, and unique architectural details that add character and charm. The sunlit primary bedroom includes an ensuite bathroom, a large walk-in closet, and a cozy seating area ideal for reading or enjoying your morning coffee. The spacious second bedroom welcomes guests with terrace access and a generous closet for added storage. The Islander Club’s resort-style amenities include a private 400' beachfront, heated pool, brand-new fitness center, two new sauna rooms, a Har-Tru™ tennis court, two pickleball courts and on-site management for true lock-and-leave convenience. The Islander Club has recently completed an extensive series of capital improvements that elevate both the structural integrity and the everyday experience of the community. Enhancements include exterior stucco repairs and balcony waterproofing, new roofs on the carports, clubhouse, and both residential towers, and modernized pool facilities with new resurfacing, tile, and equipment. Additional upgrades such as refreshed landscaping and lighting, hurricane-rated windows and doors, and a fully renovated fitness center further enhance the appeal and long-term value of the property. Whether you’re seeking a seasonal retreat or a full-time coastal home, this move-in-ready gem delivers the best of island living and peace of mind.
Listing Agent: Julie Lojacono Mackie (773-704-1438)
775 LONGBOAT CLUB RD #807, LONGBOAT KEY, FL 34228
$1,995,000277 Days on yellowkey MLS ID: A4667077
0 Days Off yellowkey (back on 6/20/2026)
REDUCED by $300,000 (13.1%) on 06/09/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1842 Built: 1984 Tax: $10,487 (2024)Community: Beaches Of Longboat Key Ph-1Condo
Taxes:$10,487
Middle School: Pine View School
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)
3806 GULF OF MEXICO DR #C209, LONGBOAT KEY, FL 34228
$335,00054 Days on yellowkey MLS ID: A4693850
2 Days Off yellowkey (back on 6/20/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Monthly Fee: $1,346 Tax: $2,934 (2025)Community: Beach Harbor ClubCondo
Taxes:$2,934
Remarks: Under contract-accepting backup offers. Discover Your Slice of Paradise! This charming turnkey 2-bedroom, 2-bath condo is perfectly positioned between the Gulf of Mexico and Sarasota Bay, offering breathtaking sunrise and sunset views. Enjoy deeded beach access complete with lounge chairs, picnic tables, charcoal grills, and outdoor showers. On the bayside, recent upgrades include a new dock with first-come boat slips, community kayaks, an electric kayak launch, and a fishing pier with a cleaning station. Host a BBQ at the tiki hut or relax by the heated pool featuring gas grills, indoor restrooms, and an outdoor shower. The newly renovated clubhouse offers an upgraded fitness center, card room, large bar, full kitchen, and plenty of gathering space for entertaining.During season, this vibrant and friendly community comes alive with Wednesday night happy hours and festive celebrations including St. Patrick’s Day, Mardi Gras, Cinco de Mayo, and more.
Listing is courtesy of: FLORIDA GALLERY REAL ESTATE (941-315-6678)
Listing Agent: Kathleen Magnus (941-281-5539)
3804 GULF OF MEXICO DR #B204, LONGBOAT KEY, FL 34228
$339,00033 Days on yellowkey MLS ID: A4696842
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 761 Built: 1970 Tax: $1,343 (2025)Community: Beach Harbor ClubCondo
Taxes:$1,343
Remarks: Welcome to coastal living at its finest in this beautifully renovated 1-bedroom, 1-bath condo at Beach Harbor Club on coveted Longboat Key. Perfectly positioned adjacent to the beach, this second-story retreat offers a peek-a-boo view of the sparkling Gulf and 761 square feet of stylish, light-filled comfort. Step inside to discover a fully updated interior featuring impact windows, a new AC system, and modern finishes throughout. Every detail has been thoughtfully considered to deliver effortless island living. The building offers convenient elevator access, plus a wealth of amenities designed for relaxation and recreation. This vibrant community stretches from beach to bay, granting you deeded beach access and a rooftop deck where unforgettable sunsets await. Cool off in the heated pool, unwind at the tiki bar, or gather with neighbors in the clubhouse. Outdoor enthusiasts will love the kayak and canoe launch, while boat slips are available first-come, first-serve for $700/year. Additional perks include a fitness center, laundry facility, bike storage, storage locker, wood shop, and on-site management. Condo fees thoughtfully cover TV, internet, and water for added peace of mind. Beyond your doorstep, indulge in the best of the region. Savor waterfront dining at Dry Dock Waterfront Grill, shop at nearby Publix, or explore the boutiques of St. Armands Circle. Anna Maria Island's charm is just a short drive away. Discover your slice of paradise—schedule your private showing today and embrace the Longboat Key lifestyle.
Listing is courtesy of: STERLING REALTY (941-379-5810)
Listing Agent: Shaun Cumston (941-737-3539)
455 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228
$2,095,000104 Days on yellowkey MLS ID: A4686984
REDUCED by $100,000 (4.6%) on 05/04/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $18,228 (2025)Community: PierreSpa: YesCondo
Taxes:$18,228
Remarks: Gulf-front living takes on a refined sense of scale in this beautifully renovated, truly move-in-ready residence at The Pierre, where every detail is already in place for effortless coastal living. Located behind the gates of the Longboat Key Club, this intimate building of just 66 residences provides privacy, security and resort style amenities. The home features more than 2,400 sq. ft. of thoughtfully updated space that blends comfort, style, and quiet sophistication A full wall of glass showcases the property’s coveted southwest exposure, filling the interiors with natural light and framing stunning Gulf of Mexico sunsets each evening. With this ideal orientation, you enjoy uninterrupted views without the need for shutters or heavy blinds. Inside, diagonal tile flooring, high ceilings, and elegant millwork create an immediate sense of openness. The great room flows seamlessly into the dining area and the reimagined kitchen, designed with black stone countertops, off-white cabinetry with glass accents, high-end appliances, and a breakfast bar. A slider opens to the terrace, enhancing the home’s indoor-outdoor connection. A private office with double-glass doors provides a quiet, flexible workspace. The serene primary suite offers terrace access, a breathtaking view, and a spacious bath with dual water closets and a distinctive circular glass-enclosed shower. Guest accommodation is inviting, and an in-residence laundry room adds everyday convenience. Residents of The Pierre on Longboat Key enjoy concierge service, under-building parking, 24-hour security, a fitness center, three guest suites, one of which is a full 2-bedroom apartment, a heated pool and spa, Har-Tru tennis courts, shuffleboard, and private beach access. Membership opportunities at the Longboat Key Club offer championship golf and fine dining, all within minutes of St. Armands Circle and Sarasota’s vibrant downtown.
Listing Agent: Bruce Myer (941-376-5311)
100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
$899,00059 Days on yellowkey MLS ID: A4693834
0 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $3,929 (2025)Community: Sands PointCondo
Taxes:$3,929
Remarks: Under contract-accepting backup offers. BACK ON THE MARKET with a New Price and Turn Key! Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, and nestled inside the gates of the Longboat Key Club. This gorgeous 1492 sq. ft. water front residence underwent a total transformation in 2023, and the results are nothing short of spectacular. Step inside this bright second floor residence and discover a two bedroom and two baths, with a view that feels serene, luxurious, and unmistakably coastal. This condo comes with a view of the private marina tucked away in a quiet cove, where you can enjoy watching the dolphins at play. Towering palm trees frame the scene beautifully, with the curved waterfront drive adds a resort-style elegance to this one-of-a-kind property. This kitchen has a bright, modern, upscale feel with a clean coastal-inspired design. White shake-style cabinetry with sleek brushed nickel handles, extending all the way to the ceiling for extra storage. Exotic granite counters, matched with a sleek white Carrara marble back splash. Stainless steel appliances, and a deep undermount sink with a tall industrial-style spring faucet. The expansive great room steals the show, with a dramatic wall of windows, open concept and LVP flooring thru out. Both bathrooms feature quartz counter tops, tiled floors and walk in showers. HVAC 2020. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room with kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. With in walking distance to well renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise 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)
2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL 34228
$1,650,00036 Days on yellowkey MLS ID: A4696213
1 Days Off yellowkey (back on 6/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1468 Built: 1972 Tax: $18,254 (2025)Community: Islands WestSpa: YesCondo
Taxes:$18,254
Remarks: Under contract-accepting backup offers. Professional Photo's coming soon. Wake up to breathtaking, direct panoramic views of the Gulf of Mexico from this stunning third-floor beachfront residence on Longboat Key. Perfectly positioned to capture endless turquoise waters and spectacular sunsets, this coastal retreat offers unobstructed Gulf views, creating a serene backdrop for everyday living. The completely updated condo features two bedrooms, two baths, a spacious great room, dining area, and a kitchen with a charming breakfast nook. Walls of impact glass flood the interior with natural light, while floor-to-ceiling windows in both bedrooms showcase the ever-changing beauty of the shoreline. A wraparound balcony provides the perfect setting to enjoy morning coffee, coastal breezes, and mesmerizing sunsets over the Gulf. Ideally located mid-island, this residence offers the perfect balance of tranquility and convenience. Bay Isles Shoppes is just across the street, offering Publix, CVS, banking, dining, the Longboat Key Tennis Center, and Bayfront Park. World-renowned St. Armands Circle is only four miles away, while downtown Sarasota's acclaimed dining, shopping, arts, and entertainment are within a short seven-mile drive. Residents of Islands West enjoy an exceptional Gulf-front lifestyle with an impressive collection of resort-style amenities. The 15-story community features secure key-fob entry, a heated beachfront pool and spa, outdoor grilling and lounge areas, tennis and pickleball courts, and dedicated storage for bicycles, kayaks, and paddleboards. The clubhouse is currently being transformed to include a stylish social room with library, state-of-the-art fitness center, and catering kitchen. Pet lovers will appreciate the welcoming two-pet policy. Experience the ultimate beachfront lifestyle where spectacular views, resort-inspired amenities, and an unbeatable Longboat Key location come together in one extraordinary residence.
Listing Agent: Midge Mccarthy (941-809-3800)
4234 GULF OF MEXICO DR #E2, LONGBOAT KEY, FL 34228
$580,000270 Days on yellowkey MLS ID: A4667654
REDUCED by $18,000 (3.0%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $10,617 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$10,617
Remarks: REDUCED AND INCREDIBLE VALUE! EXCEPTIONAL FULL BAY VIEWS, PRIVATE BEACH ACCESS AND KAYAK LAUNCH, HURRICANE-RATED WINDOWS AND SLIDERS, UPDATED BATHS AND MORE! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights in-unit laundry, 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.
Listing Agent: Lenore Treiman (941-356-9642)
615 DREAM ISLAND PL #105, LONGBOAT KEY, FL 34228
$949,00091 Days on yellowkey MLS ID: A4689957
REDUCED by $46,000 (4.6%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1293 Built: 1985Monthly Fee: $2,172 Tax: $4,735 (2025)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$4,735
Remarks: Paradise Found: Fully Renovated Luxury at Harbour Villa Club, a True Longboat Key Gem! Welcome to a slice of heaven on the pristine North-End of Longboat Key at Harbour Villa Club. This luxurious, fully renovated (2025, not from storms) waterfront condo offers a lifestyle of serene elegance, perfectly positioned to capture breathtaking, unobstructed views of the glistening Sarasota Bay, the Intracoastal Waterway, and the protected Sister Keys. Step inside this exquisite home to an open, spacious floor plan bathed in natural light, thanks to high ceilings and expansive sliders. The custom gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, ample counter space, and intelligent, creative storage solutions. The main living area is complemented by a sleek and stylish wet bar, ideal for effortless entertaining. The primary suite is a private sanctuary, designed for ultimate comfort with tremendous space, dual closets, and unparalleled water views. The equally luxurious primary bathroom features high-end fixtures, beautiful tile work, and a spacious shower. The secondary bedroom provides a generous space perfect for use as a guest suite or a flexible office. Relax or entertain year-round on your covered and screened lanai, the perfect outdoor space for sipping your morning coffee or evening cocktail while taking in the surrounding beauty. Boater's Dream and Unrivaled Flexibility: A rare and highly valuable amenity is the deeded boat slip #14, which conveys with the condo. This 40ft slip, equipped with electric, water, and new composite decking, is positioned directly outside the unit and can accommodate up to a 55'+/- vessel. Furthermore, Harbour Villa Club is one of the few Longboat Key communities with Weekly rental allowance, offering exceptional flexibility for ownership and use. Potentially generating gross approx. income of $85K annually with generous owner use availability. Community & Location: The community boasts mature tropical landscaping and grounds. Amenities include a heated pool, hot tub, outdoor grill, kayak storage/launch, boat ramp, climate-controlled bicycle/locker storage, and brand new tennis and pickleball courts. Located just a short walk to popular beaches, restaurants, and parks, and a short drive to St. Armands Circle and Downtown Sarasota. This property is more than a luxury condo—it is a complete lifestyle.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
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