Location: Longboat Key
Do Not Show Listings
4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228
$530,000116 Days on yellowkey MLS ID: A4676925
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,041 (2024)Community: Longboat HarbourCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,041
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Located in the gated waterfront community of Longboat Harbour, this updated first floor residence offers direct walkout access to manicured green space and peaceful water views. Positioned near deeded beach access, the home provides a seamless blend of coastal living and everyday convenience. Interior features include tile flooring throughout, Frigidaire appliances, plantation shutters and automated blinds. The residence is offered turnkey furnished, including a West Elm leather sofa, coordinated coastal accent tables, coffee table, breakfast set and dining table with six chairs. The air conditioning system was replaced approximately two and a half years ago. All appliances and the hot water heater are under warranty, including parts and labor, through February 2027. Covered assigned parking and ample guest parking are included. Longboat Harbour is home to the Longboat Yacht Club, offering an active social calendar and waterfront gatherings for residents, whether or not they maintain a slip. Dock slips are available on a first-come basis for $460 per year. Community amenities include kayak storage and launch, seasonal dock rentals, a fitness center with instructor-led classes, tennis and pickleball courts, sauna, craft room, woodshop, library, and game rooms. No pets permitted. Rentals allowed twice annually with a 30 day minimum.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Sharon Meier (407-927-5669)
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000302 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceSpa: NoCondo
Taxes:$5,281
Elementary School: None
High School: None
Middle School: None
Remarks: THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,600,00052 Days on yellowkey MLS ID: A4685503
REDUCED by $150,000 (2.2%) on 04/30/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2347 Built: 2024 Tax: $50,055 (2025)Community: St. RegisSpa: NoCondo
Taxes:$50,055
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Perched above the shimmering shoreline, this exquisite two-bedroom, two-and-a-half-bath residence at The St. Regis Longboat Key Resort offers breathtaking panoramic views of the turquoise waters of the Gulf of Mexico and the resort’s serene saltwater lagoon. Designed for both refined comfort and effortless coastal living, the residence showcases exceptional craftsmanship and sophisticated design throughout. A defining feature of this residence is the expansive private terrace, where all principal rooms open seamlessly to the outdoors. Complete with a gas grill, this exceptional outdoor living space provides sweeping views of the Gulf of Mexico and the tranquil lagoon—creating the perfect setting for al fresco dining, entertaining, or simply enjoying spectacular sunsets over the water. The gourmet kitchen is a true showpiece, appointed with sleek Poggenpohl cabinetry and premium appliances including Wolf double ovens, a gas cooktop, microwave, icemaker, and wine refrigerator. A generously sized island provides abundant built-in storage, making the space as functional as it is beautiful. This thoughtfully designed floor plan features two luxurious owner’s suites. The primary suite enjoys stunning views of the Gulf of Mexico and opens directly onto the large terrace. The spa-inspired bathroom features a large double vanity with elegant lighted mirrors plus a separate makeup vanity, two private water closets, a seamless glass shower, and a freestanding soaking tub. Electronic sheers and blackout shades provide effortless ambiance and privacy, while a custom-built closet offers exceptional storage. The second owner’s suite also captures captivating Gulf views and opens onto the terrace. Its spacious bath includes dual vanities with lighted mirrors, a water closet, and custom-built closets. Electronic sheers and blackout shades add both convenience and luxury. Additional highlights include a large laundry room with sink, cabinetry, and hanging rack, as well as an elegantly designed powder room for guests. Offered completely turnkey, the residence is beautifully furnished and enhanced with custom light fixtures throughout, creating a sophisticated yet inviting coastal retreat. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
1115 GULF OF MEXICO DR #304, LONGBOAT KEY, FL 34228
$899,0002 Days on yellowkey MLS ID: A4691842
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1503 Built: 1979 Tax: $9,423 (2024)Community: Beachplace ISpa: YesCondo
Taxes:$9,423
High School: Booker High
Remarks: Wonderful opportunity in the desirable Beachplace community on Longboat Key to purchase a renovated condominium with tranquil water views and coastal charm. Since it was purchased in 2019, this unit has enjoyed new hurricane-impact windows and doors, new window treatments, new laminate flooring, new white cabinetry with slab granite countertops throughout, new interior paint, new baseboards and new interior doors. The remodeled kitchen, which has been opened up to expand the view, features coastal white cabinetry with champagne pulls, stainless appliances, canned lights and tile floors. The unit comes complete with inviting furniture, a built-in owner's cabinet in the storage room, washer and dryer, making it move-in-ready or ideal for rental. With a one-month minimum rental allowed 12 times per year, Beachplace is one of the sought-after investment opportunities on Longboat Key. Residents enjoy access to an array of resort-style amenities, including a Junior Olympic-size pool, spa, fitness center, clubhouse, EV charging stations, kayak storage, tennis and pickleball courts, and 24-hour security. Just moments from Longboat Key Club, and the shops and dining of St. Armands Circle, this condominium offers a blend of convenience, lifestyle and coastal luxury. Don't miss this opportunity to own this light-filled condominium, which overlooks the serene pond with fountain that glows beautifully at night, along with partial views of the pool area and Gulf of Mexico.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Chris Wetzig (941-350-8083)
4835 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$675,00064 Days on yellowkey MLS ID: A4684056
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $10,445 (2024)Community: Westchester AptsCondo
Taxes:$10,445
Remarks: Experience direct Gulf-front living in this furnished, first-floor walkout residence at The Westchester on Longboat Key. Enjoy sweeping turquoise water views from nearly every room, with miles of pristine shoreline just beyond your door. This well-appointed, inviting two-bedroom, two-bath condominium features a spacious split floor plan designed for comfort and privacy, along with seamless indoor-outdoor living and immediate access to the pool and beach. The kitchen is equipped with stainless steel appliances, solid surface countertops, and abundant cabinetry and prep space. Both bedrooms offer en suite baths and generous walk-in closets, complemented by additional storage. The primary suite features a private screened lanai overlooking the Gulf, creating a tranquil retreat. A second expansive screened lanai off the great room captures panoramic water views and opens directly to the community pool and beach. An in-unit washer and dryer add everyday convenience. This thoughtfully designed, fully furnished residence is ideal for effortless coastal living, whether as a primary home, vacation getaway, or investment opportunity. The unit includes assigned covered parking and private storage conveniently just outside the entry. Community amenities include lighted tennis and pickleball courts, a basketball court, two heated pools, shuffleboard, outdoor grilling areas with cabanas, kayak and bicycle storage, and private beach gear lockers. A newly renovated clubhouse is coming soon and will feature a full kitchen, lending library and fitness area. Rentals are permitted, offering flexibility for seasonal or year-round use. The Westchester’s mid-key location provides convenient access to Bayfront Park with its dog parks and waterfront views, as well as nearby shopping and daily conveniences, including Publix. Residents are minutes from the Centre Shops and Whitney Plaza, along with more than a dozen popular north-end restaurants, including waterfront favorites such as Shore Restaurant and Mar Vista Dockside Restaurant. Longboat Key also offers a private golf course, a full-service marina, and multiple waterfront parks. Nearby destinations include St. Armands Circle and downtown Sarasota, renowned for its vibrant arts and cultural scene.
Listing Agent: Cindy Fischer (941-465-1124)
3040 GRAND BAY BLVD #283, LONGBOAT KEY, FL 34228
$1,799,000186 Days on yellowkey MLS ID: A4669347
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2550 Built: 1996 Tax: $18,262 (2025)Community: Grand Bay 2Spa: NoCondo
Taxes:$18,262
Remarks: Welcome to Grand Bay. Experience the essence of refined coastal living, where breathtaking panoramic water and city views take center stage. Awaken to the sunrise over Sarasota Bay’s skyline with limitless views of the bay and golf course, and unwind with stunning sunsets over the Gulf, an ever-changing display of beauty from every room. Perfectly situated on the 8th floor, this elegant home welcomes you through a private-access, controlled elevator leading to a stunning foyer framed by contemporary glass double doors. The Cayman open floor plan immediately reveals sweeping vistas, while large porcelain tile flooring flows seamlessly through the living areas and onto two outdoor terraces ideal for quiet relaxation. The stunning updated kitchen features two-toned cabinetry, Wolf and Sub-Zero appliances, under-cabinet lighting, quartz countertops, and an inviting breakfast bar. An adjacent eat-in area with floor-to-ceiling sliders opens to a private covered terrace, a perfect setting for entertaining guests and boundless vistas. The primary suite is a lavish retreat, complete with white oak floors, two walk-in closets and a spa-inspired bath showcasing, a soaking tub, glass shower, and dual vanities. The guest suite offers private terrace access for stunning sunset views, complemented by white oak floors and an en-suite bath. Discover versatility with a den/office that doubles as an occasional guest room, providing privacy with elegant pocket doors that separate it from the formal dining room, and a 3rd full bath just steps away. A well thought out conversion has added a built-in office area adding functionality to round out the interior. Residents enjoy various first-rate amenities, including 24-hour guard gates, a clubhouse, two community pools and spas, a large fitness center with saunas, and tennis courts. Stroll the neighborhood’s scenic walking paths or enjoy deeded access to the exclusive gated Bay Isles Beach Club offering locker rooms, barbecues, volleyball nets, covered picnic areas and a sandy white beach. Located behind the Bay Isles secure gates, this secluded neighborhood rests on the rolling greens of the Longboat Key Club’s golf course. Grand Bay residents find it hard to leave this special community. This residence truly captures the best refined Bay and beach lifestyle – sophisticated, exclusive, and ready to be enjoyed.
Listing Agent: Stacy Hanan (941-266-0529)
4310 FALMOUTH DR #102, LONGBOAT KEY, FL 34228
$649,90098 Days on yellowkey MLS ID: A4679011
REDUCED by $10,100 (1.5%) on 04/30/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969Monthly Fee: $1,410 Tax: $6,739 (2024)Community: Longboat HarbourCondo
Taxes:$6,739
Remarks: Recently reduced—don’t miss this opportunity. No special assessments after the 2024 storms, no history of flooding, well-funded reserves, and structural soundness supported by SIRS report! Exceptional value for a Longboat Key condo with private beach access. Enjoy deeded Gulf access with a residents-only community beach house featuring bathrooms, indoor/outdoor showers, seating, cabana space, and parking—your personal gateway to Gulf Coast living. Experience exceptional bayfront living at 4310 Falmouth Drive, Unit 102, located in the sought-after Longboat Harbour community on Longboat Key—a premier coastal city and barrier island along Florida’s Gulf Coast, renowned for attracting year-round residents, second-home owners, seasonal residents, and visitors seeking a refined, upscale seaside lifestyle. This A-Building, direct bayfront residence captures full Sarasota Bay views from the kitchen, dining area, living room, enclosed lanai, and primary bedroom—offering a front-row seat to sunrise skies, passing boats, dolphins, manatees, eagles and all kinds of exciting wildlife just 40 feet from the tranquil water vistas. Thoughtfully updated, the home features luxury vinyl flooring, upscale LG quartz Viatera Rococo countertops in the kitchen and both bathrooms, and soft-close drawers and custom cabinetry throughout. The spacious primary suite includes double vanities and a beautifully updated walk-in shower, while the guest bath also offers a walk-in shower with quartz finishes. Significant capital improvements provide peace of mind, including new hurricane-rated windows and sliders (2024, Cat5), HVAC (2021) with approximately 8 years remaining on a 12-year warranty, and a water heater (2023). The enclosed lanai expands usable living space while maintaining sweeping Sarasota Bay views. Offered fully furnished for a seamless, move-in-ready bayfront lifestyle. Longboat Harbour is a gated, resort-style community offering an impressive array of amenities, including four heated pools, tennis and pickleball courts with active player groups, fitness center, sauna, meeting rooms, billiards, putting green, woodworking shop, kayak storage, shuffleboard, locker rooms, fishing piers, two community grills, on-site management, and a protected harbor. Boat slips are available to members of the Longboat Harbour Yacht Club (subject to availability). Enjoy the best of island living with private deeded beach access just a short walk or drive across the street—complete with seating, chair storage, cabana, restrooms, indoor and outdoor showers, parking, and a convenient car-wash area. Additional features in the condo include washer and dryer connections in a hall closet and assigned covered carport parking with abundant guest spaces nearby. In the living room, open the sliders to seamlessly expand your indoor–outdoor living space, or keep them closed and enjoy the patio as an enclosed lanai—then open the glass sliders to let in refreshing coastal breezes and salt air. Located just 7.5 miles north of St. Armands Circle, and a short drive to downtown Sarasota’s Arts District, world-class dining and shopping, with Sarasota-Bradenton International Airport nearby. Direct Sarasota Bay views and private deeded Gulf beach access make this exceptional residence the ultimate Longboat Key lifestyle opportunity.
Listing is courtesy of: MARCUS & COMPANY REALTY (941-932-8550)
Listing Agent: Kerre Allman (941-909-3095)
2850 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$368,5002 Days on yellowkey MLS ID: A4691701
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 657 Built: 1967 Tax: $4,601 (2025)Community: Neptune On Longboat KeySpa: NoCondo
Taxes:$4,601
Remarks: Own your slice of paradise on Longboat Key with this charming 1-bedroom, 1-bath condo located at 2850 Gulf of Mexico Dr Unit 5. Just directly across from public beach access, this 657 sq ft ground-floor unit is perfectly positioned for both personal enjoyment and strong rental income potential. Whether you're seeking a low-maintenance vacation escape or an income-generating property, this location checks all the boxes. Walk across the street to watch sunset on the sand, then stroll to Publix, Bayfront Park's tennis & pickleball courts, the library, or one of the island’s cozy dining spots. Everything your guests—or you—could want is right at your doorstep. The unit features a bright, open living space with tile flooring, a spacious bedroom, walk-in closet and parking. The well-maintained community offers low HOA fees and a relaxing island vibe that keeps guests coming back. Don’t miss out on this rare opportunity to own on Longboat Key—whether you're investing in your future or your lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
1930 HARBOURSIDE DR #145, LONGBOAT KEY, FL 34228
$549,00025 Days on yellowkey MLS ID: A4686987
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $50,000 (8.3%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982 Tax: $8,215 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$8,215
Remarks: Under contract-accepting backup offers. Set on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residence captures sweeping views across the mangroves, a navigable channel and Sarasota Bay beyond—creating a vibrant waterfront backdrop from nearly every room. Upon entry, engineered wood flooring draws your eye to a wall of glass at the rear of the residence, where shifting blue and green tones take center stage. The layout flows effortlessly from the updated kitchen into the dining area and living room, allowing the view to remain the focal point throughout. The kitchen has been thoughtfully redesigned with striking stone countertops, low-profile white cabinetry, a refined tile backsplash and stainless-steel appliances. The living room opens to an expansive terrace through a full wall of sliders, offering a front-row perspective of the mangroves and channel, where boats pass by and manatees are often seen gliding through the water—creating a setting that feels both peaceful and connected. The primary suite serves as a private retreat with rich wood flooring, direct terrace access and a well-appointed bath featuring dual vanities and a separate water closet. The guest bedroom is comfortably sized, and the guest bath has also been tastefully updated. Residents of Fairway Bay enjoy a bayside lifestyle with deeded beach access through the private Bay Isles Beach Club, one underbuilding parking space, 24-hour gated security, walking trails, a heated pool, tennis courts and a fitness center. Membership opportunities at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available, and small pets up to 15 pounds are welcome.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
5270 GULF OF MEXICO DR #508, LONGBOAT KEY, FL 34228
$774,900151 Days on yellowkey MLS ID: A4673695
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1460 Built: 1974 Tax: $4,861 (2025)Community: The Banyan Bay ClubCondo
Taxes:$4,861
Remarks: Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.
Listing Agent: Beth Ann Boyer (941-780-6606)
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$1,095,00039 Days on yellowkey MLS ID: A4686721
REDUCED by $130,000 (10.6%) on 04/28/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3080 GRAND BAY BLVD #515, LONGBOAT KEY, FL 34228
$625,000119 Days on yellowkey MLS ID: A4674001
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1276 Built: 1996 Tax: $7,834 (2024)Community: Grand Bay 5Spa: YesCondo
Taxes:$7,834
Remarks: Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and kitchen, with double doors allowing the kitchen to be closed off for entertaining. Thoughtfully designed, the kitchen features all-white cabinetry, stone countertops and a clean, timeless aesthetic ideal for both everyday living and hosting. The primary suite is spacious and inviting, with corner sliders opening to the terrace and a well-appointed bath with dual vanities, a spa tub and a glass-walled shower. The guest bedroom is equally generous and enjoys direct terrace access. Outdoors, the expansive terrace offers unobstructed views of Sarasota Bay and the city skyline—perfect for entertaining, morning coffee or evening cocktails. Located behind the gates of Bay Isles, Grand Bay is a socially active, resort-style community offering a clubhouse, guard gate, two-car under-building parking, fitness center, two Har-Tru tennis courts, two heated pools, a spa and deeded access to the private Bay Isles Beach Club. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, private beach privileges, a full-service marina, tennis and pickleball, a luxury spa, fitness facilities and acclaimed dining.
1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$1,025,000140 Days on yellowkey MLS ID: A4674194
REDUCED by $25,000 (2.4%) on 04/29/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1707 Built: 1983 Tax: $11,336 (2025)Community: Players Club IvCondo
Taxes:$11,336
Remarks: Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.
Listing Agent: Mairead Smialek (847-334-4848)
1065 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$629,000189 Days on yellowkey MLS ID: A4669086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981 Tax: $7,875 (2024)Community: Beachplace IiiCondo
Taxes:$7,875
Remarks: One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true coastal feel. The residence features brand-new, impact-rated floor-to-ceiling sliding glass doors that brighten the living and dining areas and enhance indoor-outdoor living. The open-concept layout connects the kitchen, dining, and living spaces, making it well suited for everyday living or entertaining. A split-bedroom floor plan provides privacy, with the primary suite offering direct access to the terrace. One assigned parking space is included, and the unit is ready for personalization or updating. BeachPlace is a gated, Gulf-front condominium community offering 24-hour security and resort-style amenities, including a clubhouse, heated beachfront pool and spa, tennis courts, fitness center, and a private boardwalk with direct beach access. Seasonal beach service with lounge chairs and umbrellas is provided. Conveniently located near golf, marinas, dining, and shopping, and just a short drive to downtown Sarasota, this property offers flexibility as a full-time residence, seasonal getaway, or investment opportunity.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: John Esser (515-306-8505)
4835 GULF OF MEXICO DR #302B, LONGBOAT KEY, FL 34228
$849,900424 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)
1000 LONGBOAT CLUB RD #204, LONGBOAT KEY, FL 34228
$949,000168 Days on yellowkey MLS ID: A4671838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972 Tax: $6,901 (2024)Community: Privateer SouthCondo
Taxes:$6,901
Remarks: Sublime Gulfside Retreat at Privateer South — 1000 Longboat Club Rd #204 Experience the pinnacle of effortless beachfront living behind the prestigious gates of the Longboat Key Club. This immaculate, fully remodeled 2-bedroom/2-bath residence at Privateer South is offered turnkey furnished, presenting an immediate sanctuary of modern coastal style. Meticulously renovated with longevity in mind, the home is enveloped in impact-rated windows and sliders, ensuring quiet comfort, energy efficiency, and ultimate peace of mind. An inviting entry flows into a radiant, open-concept great room where living and dining zones transition seamlessly to the outdoors. Step onto your private covered balcony to take in unobstructed, panoramic views of the Gulf of Mexico— the ultimate backdrop for sunrise coffee, golden-hour cocktails, and the soothing sounds of the surf. Inside, cohesive coastal flooring and a sophisticated neutral palette provide an elegant canvas for personal style, accented by designer lighting and polished hardware. The renovated kitchen is a sleek culinary workspace featuring custom cabinetry, lustrous stone countertops, and premium stainless-steel appliances. The thoughtful split-bedroom layout guarantees privacy for owners and guests alike. The serene primary suite is a true retreat, offering extensive custom built-out wardrobes and a spa-inspired en-suite bath with a frameless walk-in shower. The oversized guest bedroom is equally impressive, boasting its own generous custom walk-in closet and adjacency to a second, well-appointed full bath. This residence is designed for a true "lock-and-leave" lifestyle, complete with abundant interior storage, an assigned covered parking space, and an additional dedicated storage locker. Privateer South provides an unrivaled resort experience on a pristine stretch of sugar-sand beach. Enjoy a Gulf-front heated pool and spa, tennis and pickleball courts, a modern fitness center, a vibrant clubhouse, on-site management, and 24-hour gated security, all framed by lush tropical landscaping. Comprehensive association services handle practically everything, supporting a stress-free ownership experience. Minutes beyond the shoreline lie world-class amenities: championship golf, a full-service marina, and fine dining at the Longboat Key Club (membership optional), the chic boutiques of St. Armands Circle, and the cultural vibrancy of downtown Sarasota. A rare blend of thoughtful renovation, storm-ready construction, and amenity-rich Gulfside living, Privateer South #204 is more than a condo—it’s an endless getaway.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mike Griffin (941-586-6402)
4390 EXETER DR #206, LONGBOAT KEY, FL 34228
$529,000183 Days on yellowkey MLS ID: A4670032
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $7,775 (2024)Community: Longboat HarbourCondo
Taxes:$7,775
Remarks: ~~~~~ * * * * SELLER SAYS SELL * * * * ~~~~~~~ * * * * NICEST FULL REMODEL IN LONGBOAT HARBOUR * * * * ~~~~~ PRICED BELOW MARKET VALUE ~~~~~ Enjoy island living nestled in the VIBRANT community of Longboat Harbour on beautiful Longboat Key. This UPDATED and FULLY RENOVATED condo offers a luxurious living experience with abundant amenities and stunning canal views where the Manatee play and sun bathe! Recent tastefully completed renovations include ALL NEW TILE FLOORING, NEW A/C UNIT, a fully updated gourmet kitchen with quartz counters, new cabinets, new appliances, a WASHER/DRYER IN UNIT, fully remodeled bathrooms, new doors and fresh paint throughout, a new primary WALK-IN closet, and PLANTATION SHUTTERS, that provide an interior that is both stylish and inviting. The owners opened the lanai to add more interior space to the living area with a seamless transition. No need to replace the sliders as they did that for you (NEW HURRICANE IMPACT SLIDERS) Need additional storage space? This condo also features a separate storage locker and bike/Kayak storage as well. Located in a prime location within a gated community on Longboat Key, this property is a water-lover's paradise. Boating enthusiasts will appreciate the deep-water canal access to Sarasota Bay, with boat slips available on a first come basis and additional kayak launches. Longboat Harbour is renowned for its welcoming atmosphere and an array of amenities designed to cater to every interest and lifestyle. This resort like community with an on-site manager offers a range of recreational activities including mini-golf, shuffleboard, tennis, and pickleball. Fitness enthusiasts will appreciate the large and well-equipped fitness center, complete with private locker rooms and saunas. Additionally, the beautifully renovated recreation room overlooking the bay, serves as the heart of social gatherings in Longboat Harbour, hosting a variety of clubs and activities complemented by a kitchen and dance floor. The four heated swimming pools provide relaxation and enjoyment year-round. For beach lovers, a community beach pavilion across Gulf of Mexico Drive offers residents private, PRIVATE DEEDED BEACH ACCESS with a cabana, parking, restrooms, and dressing areas. Witness breathtaking sunrises, spot manatees, and savor stunning sunsets from this serene beachfront location. This exceptional opportunity offers an unparalleled lifestyle in one of Longboat Key's most active, social, and vibrant communities! Seize the opportunity to experience waterfront living at its finest. Schedule your private showing today.
Listing Agent: Sheryl Vanduren (720-384-4884)
1445 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$865,00067 Days on yellowkey MLS ID: A4683660
1 Days Off yellowkey (back on 4/29/2026)
REDUCED by $59,900 (6.5%) on 04/24/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1933 Built: 1982 Tax: $10,149 (2025)Community: Players Club IiiCondo
Taxes:$10,149
Remarks: Welcome to Residence #103 at 1445 Gulf of Mexico Drive, located within the prestigious Players Club on Longboat Key. This exceptional 550-foot Gulf-front community offers an unparalleled coastal lifestyle, and this residence presents a rare opportunity—available for the first time in 37 years. Originally the building’s model home, this thoughtfully designed condominium combines timeless elegance with spacious comfort. This beautifully maintained residence features three bedrooms, two and a half baths. The third bedroom/den is complete with twin Murphy beds and built-in storage. The spacious living and dining area opens to a wall of sliding glass doors leading to an expansive 30-foot open-air balcony, where you will enjoy sweeping views of the Gulf of Mexico, overlooking the 70-foot heated saltwater swimming pool, spa, lush tropical landscaping, and breathtaking sunsets. Just steps from the pristine beach, this outdoor retreat invites you to relax, read, listen to the waves, and savor spectacular evening skies. Inside, the home offers a seamless blend of style and functionality. The spacious primary suite features sliding glass doors to the balcony, a generous walk-in closet, and a split en-suite bath with dual vanities, a spa-like soaking tub and shower, and a large window that fills the space with natural light. The second en-suite bedroom, privately positioned off the front hallway, is generously sized, offers abundant natural light, and includes a large walk-in closet—perfect for guests. Additional conveniences include a powder room, in-unit laundry, interior storage, and a private storage closet just outside the front door. The residence also includes assigned under-building parking and access to bike storage. Residents of Players Club enjoy resort-style amenities, including a newly renovated clubhouse with a state-of-the-art fitness center, library, catering kitchen, and inviting indoor and outdoor social spaces. Four Har-Tru tennis courts, pickleball, a putting green, beautifully maintained grounds, a security gate, and on-site management provide both luxury and peace of mind. Ideally situated on the desirable south end of Longboat Key, this community is just minutes from Publix, the renowned St. Regis Longboat Key Resort, the upscale boutiques and fine dining of St. Armands Circle, and the vibrant cultural attractions of downtown Sarasota. This is a rare opportunity to own a distinguished Gulf-front residence in one of Florida’s most sought-after coastal communities—where luxury, location, and lifestyle come together beautifully.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
775 LONGBOAT CLUB RD #203, LONGBOAT KEY, FL 34228
$1,750,000207 Days on yellowkey MLS ID: A4667025
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $14,781 (2024)Community: Beaches Of Longboat Key Ph-1Spa: YesCondo
Taxes:$14,781
Remarks: Welcome to your dream beachfront retreat, nestled behind the exclusive gates of the prestigious Longboat Key Club. This exquisite 3-bedroom, 3-bathroom Gulf-front residence captures breathtaking, unobstructed views of the sparkling turquoise waters of the Gulf from every room—an ever-changing canvas of sunlight, sea, and sky. From the moment you enter, you're greeted by expansive walls of glass that bathe the interiors in natural light and frame the stunning panoramic seascape. Every corner of this residence is infused with the tranquil energy of the ocean, from the shimmering waves to the soft sea breezes that drift through the impact-rated sliding glass doors and windows. The spacious open-concept living and dining area is designed for effortless entertaining, offering a front-row seat to the water. Whether hosting friends or enjoying a quiet evening at home, you'll savor the endless horizon stretching beyond your wraparound balcony—a perfect place to sip morning coffee at sunrise or unwind at sunset. The Kitchen has abundant counter space, generous storage, a built-in desk, and a charming breakfast nook overlooking the beach. Each of the three expansive bedroom suites offers privacy and comfort, with en-suite bathrooms, ample closet space—including dual closets in the primary suite. Freshly painted interiors, electronic shades in every room and new carpeting in the primary suite add a fresh, move-in-ready feel. Unlike many condominiums, this residence offers the space and storage of a single-family residence, including in-unit laundry and generous closets throughout. And with no neighboring buildings in sight, you'll enjoy uninterrupted views and a sense of peaceful seclusion rarely found in beachfront living. Step outside and indulge in resort-style amenities at The Beaches, including 24-hour concierge services, two Har-Tru tennis courts, a heated beachfront pool and spa, fitness center, and a club room with catering kitchen. Mere steps from your door lie the powdery white sands and warm waters of the Gulf—perfect for sunbathing, shelling, or a sunset stroll. For the ultimate in luxury, residents may also join the renowned Longboat Key Club, offering access to two championship golf courses, a world-class spa & wellness center, tennis courts, fine dining restaurants, and a deep-water marina. Located on the coveted south end of Longboat Key, you're just minutes from the chic boutiques and dining of St. Armands Circle and the vibrant arts and culture of downtown Sarasota. This is more than a home—it’s a lifestyle. A rare opportunity to own a slice of paradise where the Gulf meets the sky. Welcome to beachfront living at its most luxurious.
Listing Agent: Courtney Tarantino (941-893-7203)
350 GULF OF MEXICO DR #211, LONGBOAT KEY, FL 34228
$938,500211 Days on yellowkey MLS ID: A4667037
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2394 Built: 1992 Tax: $9,083 (2023)Community: Tangerine Bay ClubCondo
Taxes:$9,083
Tax Year: 2023
Remarks: Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No current assessments and meticulously maintained grounds. Thoughtful floor plan with multiple terrace access points to enjoy morning and afternoon sun. This three-bedroom, two-and-a-half-bath, plus den, includes an oversized private two-car garage. There is also a natural gas barbecue on the front terrace. Resort-style amenities at Tangerine Bay Club include a heated pool, lap lane, heated spa, tennis, and regulation pickleball courts, a clubhouse with a fitness center, and a vibrant social room and calendar (happy hours, pickleball, cultural excursions). Freshly renovated boat dock, two kayak launches, a fishing pier, and prime fishing directly on Sarasota Bay. Enjoy just “sittin’ on the dock of the bay” watching the dolphins roll in. Take a scenic nature walk between Sarasota Bay and Quick Point Nature Preserve. Ownership includes (optional) membership to the Bay Isles Beach Club facilities for just $600.00 per year (application required).Longboat Key is renowned for golf, tennis, fine dining, boating, and world-class fishing. Be sure to explore the newly opened St. Regis resort, just a short stroll to the north on the beach side. Ongoing management ensures a carefree ownership experience with no special assessments anticipated. Recent capital projects (painting, waterproofing, elevator rebuilds, 2024 roof replacements, exterior tile walkway updates) have been completed and funded, with milestone inspections cleared. Pet-friendly, gated entry, and a day dock for fishing. This residence offers the perfect blend of luxury, convenience, and peace of mind—an ideal retreat for those seeking sophistication and coastal living at its finest. DON’T JUST THINK ABOUT IT, COME EXPERIENCE IT FOR YOURSELF AND MAKE IT YOUR REALITY.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
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