Location: Longboat Key
Do Not Show Listings
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,999,95080 Days on yellowkey MLS ID: A4680080
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $9,861 (2025)Community: PierreCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,861
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: 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)
1932 HARBOURSIDE DR #242, LONGBOAT KEY, FL 34228
$599,0007 Days on yellowkey MLS ID: A4688978
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982Monthly Fee: $81 Tax: $7,099 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$7,099
Middle School: Pine View School
Remarks: Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This turnkey furnished move-in ready two-bedroom, two-bathroom residence presents an exceptional chance to enjoy the Longboat Key lifestyle along with the rare advantage of one under building garage parking space. Enjoy peaceful views of Sarasota Bay, surrounding mangroves, and native wildlife from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ready for immediate enjoyment as a primary home, seasonal retreat, or investment opportunity. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1000 LONGBOAT CLUB ROAD #1105, LONGBOAT KEY, FL 34228
$1,050,000293 Days on yellowkey MLS ID: A4657701
1 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1290 Built: 1972Monthly Fee: $209 Tax: $7,027 (2024)Community: Privateer SouthCondo
Taxes:$7,027
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Seller wants offers! Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the luxurious St. Regis Resort. This island gem has brought many years of joy to the Seller based on its perfect South LBK beachside location and all it's resort style amenities. The sleek European style interior boasts carefree luxury vinyl plank flooring, along with new carpeting in both bedrooms, LED lighting, dazzling designer tile in both bathrooms, and the color scheme throughout mirrors its direct seaside setting. The open-concept kitchen makes entertaining a breeze and offers gorgeous quartz counter tops, custom backsplash, stylish GE appliances, sparkling hardware, and a customized breakfast bar. Both the primary and guest bedroom each lead to a separate balcony where you can soak up the sun while enjoying the peaceful surroundings and endless water and beach views. Residents enjoy the convenience of on-site management, an updated guest suite & additional guest quarters for your overflow visitors, a secure lobby, tennis and pickle ball, heated pool and spa, a great gym, and a refurbished lobby, hallways, social room, community bathrooms, and the landscaping create an even more exceptional experience in this world-class beach location. A membership to Longboat Key Club’s exceptional offerings will provide many hours of outdoor fun and golf & tennis enthusiasts will appreciate the two championship courses & tennis gardens. These facilities, along with professional instruction and well-appointed pro shops, cater to athletes of all levels. Outside the gates, Longboat Key offers fine & casual dining, deep water boating & fishing, 10 miles of sugar sand beaches, and a great variety of local treasures to explore. The Sarasota Opera & Ballet, Van Wezel Performing Arts, and all of Sarasota's cultural offerings including boutique shopping and popular restaurants are just minutes away, creating the perfect balance of relaxation and activity in this sought-after island paradise.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
509 SPANISH DR N, LONGBOAT KEY, FL 34228
$369,0007 Days on yellowkey MLS ID: N6143864
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1967 Tax: $6,955 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$6,955
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: STEPS FROM THE BEACH.....WATERFRONT COMMUNITY......DEEDED BEACH ACCESS......FULLY RENOVATED..........IMPACT WINDOWS..........COMMUNITY POOL...........Just **432 steps from the beach**, this is where coastal living stops being a dream and becomes your daily rhythm. Morning walks on soft sand, sunset returns under glowing skies, and the constant sense that the water is always just around the corner. **Fully renovated and never lived in**, this Longboat Key retreat feels brand new in every way — a clean, beach-inspired design with effortless flow and natural light throughout. Featuring **quartz countertops, impact windows, and a brand new water heater**, every detail has already been perfected so you can arrive and immediately exhale. Set within a **quiet waterfront community with deeded beach access**, life here feels unhurried and private, yet connected to everything that defines coastal luxury. From **boating access and a nearby pool** to the walkable, relaxed atmosphere residents cherish, it’s a setting designed for ease, not effort. With your own **covered parking and driveway**, and just minutes to **St. Armands Circle, Sarasota, and Anna Maria Island**, you’re positioned in one of the most desirable corridors on the Gulf. This is the rare combination buyers wait for — **newly finished, never occupied, and this close to the shoreline** — where every day feels like a quiet escape, and every return home reminds you why you chose it.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Garrett Sedlacek (913-461-6882)
311 FIREHOUSE CT, LONGBOAT KEY, FL 34228
$2,399,000209 Days on yellowkey MLS ID: A4665445
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2352 Built: 2005Monthly Fee: $467 Tax: $29,195 (2025)Community: Conrad BeachSingle Family
Taxes:$29,195
Remarks: This is West Coast of Florida living at its finest, designed for those seeking a refined and effortless second home near the Gulf. Elevated and elegantly appointed, this custom residence is ideally located west of Gulf of Mexico Drive in the highly desirable Conrad Beach community on Longboat Key, where coastal serenity meets thoughtful design. Surrounded by lush tropical landscaping with accent lighting, the home blends timeless island architecture with modern comforts ideal for seasonal or extended stays. Inside, an open and inviting floor plan centers around a gourmet kitchen featuring a large quartz island perfect for entertaining, abundant workspace, and seamless flow into the main living areas. A full in-house generator provides peace of mind while you are away, making ownership as easy as it is enjoyable. Multiple porches and terraces, including a rooftop observation deck, create exceptional indoor-outdoor living and invite you to savor Gulf breezes and unforgettable West Coast Florida sunsets. The primary suite, located on the main living level, offers a private retreat with a spa-inspired bath and a serene balcony overlooking the tropical surroundings. Upstairs, guest bedrooms and a spacious loft-style family room provide flexible accommodations for visiting friends and family, all with access to wraparound terraces that capture the beauty of the island setting. The home comfortably sleeps ten, making it ideal for hosting while still maintaining privacy and comfort. Outdoor living is equally well designed, with expansive decks perfect for quiet mornings or relaxed gatherings. A beautifully landscaped path leads to the oversized resort-style community pool, complete with bath facilities and entertaining space, offering all the benefits of a luxury amenity without the responsibility of maintaining a private pool. From the community observation deck, enjoy glimpses of the Gulf and dramatic evening skies. Favorite features include high-impact windows and doors, full house generator and 5 minute walk to the soft powder sand beaches and beautiful Gulf waters. The award-winning Conrad Beach community enhances the lock-and-leave lifestyle with lawn care, irrigation, and landscaping services included. Just moments from pristine beaches, the charm of Longboat Key’s north end, marinas, and the dining and boutiques of St. Armands Circle, this home offers the ideal blend of privacy, convenience, and coastal living. Schedule your private showing and experience how effortless owning a second home on Florida’s West Coast can be.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
5270 GULF OF MEXICO DR #508, LONGBOAT KEY, FL 34228
$774,900140 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)
6750 GULF OF MEXICO DR #151, LONGBOAT KEY, FL 34228
$499,00039 Days on yellowkey MLS ID: A4685668
REDUCED by $1,000 (0.2%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1969 Tax: $3,054 (2025)Community: Whitney Beach CondoSpa: NoCondo
Taxes:$3,054
Elementary School: None
High School: None
Middle School: None
Remarks: If you've been waiting for one of the best water views in Whitney Beach then wait no longer. Highly desired second floor unit allows you to sit and relax on the lanai and watch the dolphins and Manatees play. Momma manatees bring their babies into this spot to teach them and you will spot them riding around on mommas back its a beautiful sight. The dolphins come in early and around dinner to feed. The multitude of bird callings and sightings will amaze you in this tranquil spot. It's hard to find better flora and fauna just outside your back door. The property has had some nice updates and there is a total open concept feel between the kitchen and living areas. Whitney Beach community is a beach to bay community and has a path the leads you to the white sand and turquoise waters of the Gulf of Mexico where there are chairs awaiting your arrival. This is a very active community of owners who play tennis, pickleball, and shuffle board together. Kayaking and boating are available and you get your own boat slip once assigned from the current list. This is an extremely walkable community one of the most walkable to restaurants and coffee shops, liquor store and boutique shops as well as a gym and pilates center. It's a slice of heaven in paradise in one of the nicest zip codes in America. Start living!!!
Listing is courtesy of: COASTAL KEY REALTY LLC (941-993-9380)
Listing Agent: Amy Jones (941-993-9380)
1065 GULF OF MEXICO DR #603, LONGBOAT KEY, FL 34228
$799,000150 Days on yellowkey MLS ID: A4671687
2 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1503 Built: 1981 Tax: $8,908 (2024)Community: Beachplace IiiSpa: YesCondo
Taxes:$8,908
Remarks: Beachplace Penthouse with Gulf Views — Top-Floor Residence with Direct Beach Access Discover an inviting top-floor retreat in Building 10 at Beachplace, offering direct access to the Gulf of Mexico and wide views of the community’s lush landscape, sparkling shoreline, and partial Bay vistas. This furnished 6th-floor residence provides a bright coastal setting, ready for your personal touch. New impact floor-to-ceiling sliders and windows (2024) illuminate the more than 1,500-square-foot layout, bringing natural light into the open living and dining areas and connecting seamlessly to the beach-to-bay terrace. The kitchen sits at the center of the home and offers an efficient design with eating space, breakfast bar seating, and laundry closet. The split-bedroom layout enhances privacy. The primary suite includes terrace access, built-in closet with dressing area, and an en-suite bath. The guest suite, located on the opposite side of the residence, is positioned to enhance privacy. Additional conveniences include one under-building parking space (deeded, covered) plus additional outside parking, and generous storage. Beachplace is a gated Gulf-front community known for resort amenities and well-managed operations. Residents enjoy 24-hour security, on-site management, a large clubhouse, fitness center, tennis courts, walking paths, and a Gulf-side sundeck with heated pool and spa. A private boardwalk leads directly to the beach. The community’s amenities also include a spa, sauna, meeting rooms, and beautifully maintained grounds. Ideally positioned along the southern end of Longboat Key, this residence places you minutes from the island’s best recreation and conveniences. Enjoy nearby marinas, championship golf at the Longboat Key Club, waterfront dining, and the boutiques of St. Armands Circle. Downtown Sarasota—home to world-class arts, theaters, galleries, and the Bayfront Park—lies just over the bridge. With wide beaches, tropical landscaping, and exceptional amenities, Beachplace offers an effortless coastal lifestyle in one of Sarasota’s most desirable Gulf-front settings.
Listing Agent: Roger Pettingell (941-387-1840)
1211 GULF OF MEXICO DR #505, LONGBOAT KEY, FL 34228
$1,499,000158 Days on yellowkey MLS ID: A4670789
REDUCED by $26,000 (1.7%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1598 Built: 1985 Tax: $14,271 (2024)Community: PromenadeSpa: YesCondo
Taxes:$14,271
Remarks: Under contract-accepting backup offers. No matter where you 'summer' you belong in sunny Sarasota for the 'winter'. Feast your eyes on this TURN-KEY FURNISHED, BEACH FRONT condo. Your job? BRING YOUR LUGGAGE ... everything else is here! This lovely Longboat Key condo is beautifully furnished, fully equipped and calling your name. Renovated and reimagined for casual living just a few years ago, it features an open kitchen, gulf front balcony dining, fabulous wet bar and a cozy living room for quiet moments by the fire. The sleeping areas are split for maximum privacy for you and your guests. The primary suite is everything you'd hope for - gulf views from your bed, a truly exceptional ensuite bath, plenty of closet space plus a private make up area. The guest room is comfortably furnished, quiet and also offers its own view. Tile flooring throughout, full size laundry equipment, storage galore, custom window coverings and so much more. This beautiful complex is among LBK's most sought after, thoughtfully designed for resident comfort and security, well managed and impeccably maintained. The unit has been only gently used by its owners and NEVER RENTED, although leasing is ok. The complex provides concierge, private beach access, heated pool and spa, tennis, fitness and sauna areas, community rooms for parties, BBQ, sunny patio and so much more. You'll appreciate a storage locker as well as both an assigned parking spot and plentiful guest parking. 5 minutes to the Longboat Key Club or Publix, 10 minutes to St Armands. 15 minutes to downtown Sarasota. Leave the snow behind ... the sun is shining and it will be 80 degrees today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Sharon Whalen, Pa (941-957-8805)
510 WEDGE LN, LONGBOAT KEY, FL 34228
$1,990,000192 Days on yellowkey MLS ID: A4668133
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1967Monthly Fee: $17 Tax: $14,551 (2024)Community: Country Club Shores Sec 02Single Family
Taxes:$14,551
Remarks: Welcome to your own piece of paradise in the prestigious Country Club Shores community on Longboat Key. This completely renovated 4-bedroom, 3-bath coastal retreat was taken down to the studs in 2012 and rebuilt with exceptional attention to detail—offering the rare combination of timeless style, modern infrastructure, and effortless move-in readiness on a tranquil canal. From the ground up, every major system has been upgraded for peace of mind: new water and sewer lines, updated electrical throughout, impact-rated doors and windows, a resurfaced saltwater pool and with new pool heater. Newer seawall and dock, gas that was run to the house with no propane tank to worry about. No component was overlooked. The result is a home that lives like new yet radiates refined coastal charm, with most of the beautifully curated furnishings remaining with the property. Inside, you’ll be welcomed by a bright, open-concept design featuring beautiful, engineered wood floors, custom beadboard ceilings, with beams, elevated ceiling heigh in the main living room and a soothing palette of sea-glass blues and clean whites. The heart of the home is a gourmet kitchen outfitted with stainless steel appliances, designer pendant lighting, and stylish lattice-front cabinetry. A large island anchors the space, perfect for entertaining, while the adjacent living area boasts custom-built-ins, a sleek gas fireplace, and expansive views that flow effortlessly outdoors. Each bedroom is designed for comfort and privacy, with spa-inspired bathrooms that feature elegant tile work, modern fixtures, and soft lighting. The primary suite is a retreat of its own, with custom shelving, cozy window seats, and lush garden views through plantation shutters. Step outside to experience Florida living at its finest. The spacious screened lanai surrounds a sparkling heated saltwater pool and paved deck, creating a private oasis perfect for lounging, swimming, or dining alfresco in total comfort. Just beyond, a large, newer dock awaits, offering deep-water canal access—an ideal setup for avid boaters and water lovers. The deck overlooking the canal is a peaceful setting for morning coffee or an evening cocktail This home also offers exclusive deeded beach access, just a short walk or bike ride away, where you can soak in the soft white sands and turquoise waters of the Gulf. When it’s time to explore, the renowned boutiques and fine dining of St. Armands Circle are just down the street, offering vibrant nightlife, unique shopping, and gourmet experiences in a picturesque coastal setting. A short drive over the scenic Ringling Bridge takes you to downtown Sarasota, a cultural haven known for its art galleries, theaters, opera house, and waterfront dining. Whether you're strolling through the Saturday farmers market, taking in a performance at the Sarasota Opera, or enjoying waterfront cocktails at Marina Jack, the city provides an enriching blend of sophistication and coastal charm. With its ideal location, timeless design, and luxurious updates, this home offers the very best of Longboat Key living—a rare opportunity to enjoy both boating and beachside leisure in one of Florida’s most coveted communities.
Listing Agent: Courtney Tarantino (941-893-7203)
865 LONGBOAT CLUB RD, LONGBOAT KEY, FL 34228
$18,700,000210 Days on yellowkey MLS ID: A4665431
0 Days Off yellowkey (back on 4/13/2026)
Bed: 6 Bath: 7.0 Gar: 4 Liv Area Sq Ft: 9328 Built: 2001Monthly Fee: $129 Tax: $89,855 (2024)Community: Regent CourtSpa: YesSingle Family
Taxes:$89,855
Remarks: Regent’s Court: The Pinnacle of Luxury on Florida’s West Coast Regents Court: Where Legend Meets Luxury Beyond the gates of the Longboat Key Club lies an estate that doesn’t just live — it performs. A dramatic masterpiece perched on Florida’s west coast, this estate commands over an acre of pure beachfront with 150 feet of unspoiled Gulf frontage, where sky and water fuse in ever-changing hues at dawn and dusk. Your arrival is nothing short of cinematic: majestic wrought-iron gates part to reveal a sweeping driveway paved in artistic stone, each curve leading closer to the heart of the home. A side-entry garage, cavernous in its capacity, hides generous storage; beside it, a full-house generator promises unbroken comfort even when the world goes dark. Inside, every surface and silhouette feels sculpted for impact. Cream marble floors echo with light. Designer lighting drapes each room in mood and elegance. Premium stainless steel appliances anchor a gourmet kitchen, with a bar area that’s built for both intimate soirées and lavish celebrations. Across stately arches, French doors open into an office and dining space. Ascend via elevator through all four levels, each floor unveiling rooms with cathedral ceilings, balconies with sweeping views over the Gulf. The two-story library has custom woodwork. Adjacent to the large primary bedroom is the super-master bath with both tub and shower framing the Gulf in panoramic glory. On the second living level are three guest suites with private porches that render a daily spectacle — mornings bathed in soft dawn light over the sand dunes and the Gulf, evenings lit by fading sun dancing across the waves. French doors open wide, blurring the boundary between indoors and the beach. The third living level includes an all inclusive guest quarters—your private sky-retreat. Two bedrooms, two baths, a full kitchen, a spacious living and TV room. From its large, sweeping porch, the views stretch across Sarasota Bay and the Gulf’s glassy expanse. By day the Bay shimmers under sunlight, by dusk the city lights begin their soft glow. This is a space where family, friends—or guests—can escape, entertain, or simply soak in nature’s most breathtaking performances. Outside is not secondary, but rather the heart of this sanctuary. Lush tropical landscaping surrounds the estate. There is a NCAA lap pool with motorized cover, a deck edged with gas torches, fire pits that flicker under the stars. There’s an outdoor ice tub plus an outdoor kitchen with refrigerator and a gas grill. A special gym on the second floor is cooled to perfection, central control at your fingertips. Roll-safe shutters provide safety without sacrificing style. At every moment, this home evokes a rare elegance — you’re not just observing the sunset over the Gulf, you are enveloped by it. Minutes from Sarasota, St. Armand’s Circle, Anna Maria — yet here, time moves differently, more luxuriously. This is not just a home. This is a legacy.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
4955 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$5,650,00034 Days on yellowkey MLS ID: A4686511
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3122 Built: 2007Monthly Fee: $6,860 Tax: $23,380 (2025)Community: PositanoSpa: YesCondo
Taxes:$23,380
Remarks: Completely redone with the highest detail to finishes just finished in 2025! Spectacular walkout to the beautiful beach and azure Gulf of Mexico from this first floor beachfront condo that features a private pool and spa. Positano, a 10 acre oasis with only 29 residences, has a full time security and a gated entrance. This is Florida living at its very best! A fantastic wrapping terrace on the gulfside offers outdoor enjoyment from the main living area and master suite with steps leading down to the private pool. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom all with private baths is 3343 square feet. A Gulf front gourmet kitchen with state-of-the art appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows dramatically overlook the Gulf of Mexico and beach. This home has a private elevator which leads to a home with beautiful wood floors, 10 foot ceilings, crown molding and comes with a private enclosed over size garage. The Owners' Club amenities include a state-of-the-art fitness center, catering kitchen, lounge with a fireplace, Plasma TV and surround sound system. There is a 75 foot olympic pool and spa plus outdoor grilling and shaded cabanas. The grounds are lush with tropical foliage and meticulously maintained
6700 GULF OF MEXICO DR #118, LONGBOAT KEY, FL 34228
$387,561170 Days on yellowkey MLS ID: A4670555
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 990 Built: 1969 Tax: $6,431 (2024)Community: Whitney BeachCondo
Taxes:$6,431
Remarks: ...shortstories " all the buildings look alike...the photo in picture is of whitney beach condo building ..... Welcome to your private waterfront getaway. This beautifully renovated first floor residence offers tranquil Bay views, easy Bay access and your own boat dock---perfect for boating enthusuasts. Enjoy peaceful water views from the living room and entertainer's kitchen, thoughtfully redesigned with new cabinetry, countertops and stainless steel appliances. Every detail has been updated after the subject property was hit by hurricane in 2024.. including a new washer and dryer, making this condo truly move-in ready. Located in the highly sought-after Whitney Beach Bayside community, residents enjoy exceptional amenities such as two heated pools, fishing dock, kayak launch and storage, boat slips. A liberal rental policy allows one month rentals up to six times annualy. Just steps across the street is deeded beach access where you can stroll the powdery soft sand, swim in the turquoise Gulf waters, and take in breathtaking sunsets. Tennis and pickleball courts, barbecue and picnic areas and charming tiki huts are available to residents. Whitney Beach is located close to shopping areas and has many excellent restaurants. You are only a few miles from world famous St. Armands Circle and downtown Sarasota for cultural events. This is coastal living at its finest!!!
Listing Agent: Gerald Cunningham (941-321-8848)
3311 SABAL COVE DR, LONGBOAT KEY, FL 34228
$2,450,000103 Days on yellowkey MLS ID: A4676501
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3416 Built: 2006Monthly Fee: $116 Tax: $12,784 (2025)Community: Sabal CoveSpa: NoSingle Family
Taxes:$12,784
Remarks: Expertly designed by the highly regarded John Cannon Homes, known for exceptional quality and craftsmanship, this custom 4 bedrooms plus study residence offers the comfort and convenience of expansive living on one single level within the exclusive enclave of Sabal Cove, behind the secure gates of Bay Isles on Longboat Key. The home is centered around a dramatic screened outdoor living area, where the primary gathering spaces and owner’s suite are open to a grand, tiered brick-paver patio created for easy, elegant entertaining. This resort-style environment includes a saltwater swimming pool with waterfall feature, a raised gas fire pit with lounge seating and a built-in protected summer kitchen all surrounded by architectural lighting and mature tropical plantings beyond the enclosure that ensure privacy and tranquility. Spanning more than 3,400 square feet, the interior reveals impressive architectural scale with ceiling heights ranging from 12 to 15 feet, complemented by clerestory windows that fill the home with natural light. The family room is highlighted by a newly refinished limestone and glass natural gas/electric fireplace, while seamless aquarium-style glass corner sliders retract completely, creating a fluid connection between indoor living and the outdoor retreat. Interior spaces include a formal living room, a dining room with built-in glass display shelving, and a private study featuring extensive custom cabinetry. The well-appointed kitchen with a center island and breakfast bar, quartz countertops, generous custom storage, and a six-burner Thermador gas range is ideal for culinary pursuits. Additional features include hurricane impact-rated windows, wood flooring, solid-core interior doors, detailed tray ceilings and handcrafted millwork. A side-entry brick-paver drive leads to an oversized three-car garage equipped with a 240-volt EV charging outlet. Sabal Cove is an intimate community of just 38 single-family custom homes at the southern end of Longboat Key. Bay Isles residents enjoy access to a private, gated Gulf-front beach club, with optional membership to the adjacent Longboat Key Club offering 45 holes of championship golf and a premier tennis facility. Convenient to the Longboat Key Town Center’s grocery & pharmacy, the property is also a short drive to St. Armands Circle and downtown Sarasota, known for its cultural attractions, acclaimed dining, and upscale shopping.
435 L AMBIANCE DR #J704, LONGBOAT KEY, FL 34228
$2,995,000145 Days on yellowkey MLS ID: A4673061
REDUCED by $200,000 (6.3%) on 04/13/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2634 Built: 1994 Tax: $20,474 (2024)Community: L Ambiance At Longboat Key Club Ph 02Spa: YesCondo
Taxes:$20,474
Remarks: Rarely available, this 7th floor, 3 bedroom, 3 bath condo with perfect east/west views offers total privacy. Relax, unwind, and enjoy the magnificent views of the pristine sandy beach and the blue waters of the Gulf of Mexico from this unit in L ambiance. Turn around to the east and watch the boats on Sarasota Bay, and enjoy the lush fairways of the Longboat Key Golf Club. This well-designed unit is very private and does not face any adjacent buildings. The kitchen has been opened to the living areas to take advantage of the views in both directions and to entertain effortlessly. Your large private terraces are the perfect setting for enjoying a morning coffee while viewing beautiful shimmering sunrises over Sarasota Bay, and then enjoying a cocktail with the sunset every evening over the sparkling Gulf of Mexico. The Gulfside master suite opens to outstanding panoramic Gulf and beach views. Beautiful wood floors flow seamlessly throughout the open floor plan, offering a casual, elegant feel to this home. Perfectly set behind the private gates of the Longboat Key Club, you are surrounded by all the L ambiance has to enjoy, including a resort style pool with lap lanes, spa, and splash pool located on a massive outdoor lanai with gazebos and abundant seating, 2 lighted Har-Tru tennis courts, fitness center, saunas, recreation room, on-site management with 24-hour security, walking trails and over 1,200 feet of pristine beach. Your move-in ready home is waiting for you to start enjoying the paradise we call Longboat Key.
2012 HARBOURSIDE DR #2104, LONGBOAT KEY, FL 34228
$895,000216 Days on yellowkey MLS ID: A4664458
Bed: 3 Bath: 3.0 Gar: 5 Liv Area Sq Ft: 2135 Built: 1985 Tax: $9,417 (2024)Community: Fairway Bay 2 Ph 2 & 3Condo
Taxes:$9,417
Remarks: Discover Refined Coastal Living at Fairway Bay Impeccably renovated from top to bottom, this three-bedroom, three-bath end-unit townhome offers the perfect blend of style, function, and coastal charm. With 2,135 square feet of thoughtfully designed living space plus an expansive 1,516-square-foot garage and storage level, the residence provides a total of 4,050 square feet under roof. The versatile loft, vaulted ceilings, and open-concept great room create a bright, welcoming ambiance, enhanced by hardwood floors, crown molding, and a wood-burning fireplace. The gourmet kitchen boasts newly updated cabinet doors (Nov. 2023), sleek appliances (2018), and an ideal flow into the dining and living areas, which open to a screened 7’ x 22’ lanai with direct access to the backyard and grill pad. Outdoor living is further enriched by private wooden decks off both the loft and the primary suite, perfect for relaxing or sunbathing. This immaculate home is move-in ready, with extensive updates including new HVAC (July 2024), vinyl plank flooring (Dec. 2023), new carpet (March 2023), a renovated shower in Bedroom 2 (Jan. 2024), updated bathroom fixtures (Jan. 2024), and a newer water heater (2018). Additional highlights include custom closets, a central vacuum system, and two inviting terraces. Fairway Bay II offers a host of amenities just steps away, including a clubhouse, swimming pool/spa, fitness center, and on-site management. Residents also enjoy access to the exclusive Bay Isles Beach Club, with private Gulf-front swimming and sunbathing. Combining elegant updates, generous storage, and a premier Longboat Key lifestyle, this home is truly a must-see.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
527 SUTTON PL, LONGBOAT KEY, FL 34228
$349,000101 Days on yellowkey MLS ID: A4677642
REDUCED by $26,000 (6.9%) on 04/08/2026
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1088 Built: 1972 Tax: $2,054 (2024)Community: Sutton PlaceCondo
Taxes:$2,054
Remarks: Live the Longboat Key lifestyle in this beautifully updated two-story, two-bedroom townhome, where more than $60,000 in upgrades and improvements create the perfect blend of comfort, style, and coastal charm . Features include a private deeded beach, 2 heated pools, garage, pet-friendly, a marina with boat slips, and outdoor entertaining space. Offered furnished and move-in ready. Every room reflects thoughtful, elegant design, from curated furnishings to refined color palettes. The first floor features beautiful tile flooring and numerous upgrades, including a stunning kitchen with quartz countertops and backsplash, custom cabinetry, a designer sink and faucet, Bathrooms have been tastefully updated with designer fixtures, and smart recessed lighting enhances the ambiance throughout the home. Spacious bedrooms offer ample closet space and excellent storage throughout. Upstairs, elegant dark engineered wood flooring complements the tiled bathroom, creating a warm and sophisticated retreat. The enclosed lanai provides versatile bonus space ideal for a home office or family room. Additional highlights include an A/C system with iWave-R ionization generator, washer and dryer in unit, a private garage with extra storage, an electric kayak lift with 2 tandem kayaks included. . A lovely, remodeled community room, BBQ, a private beach pavilion with parking and restrooms. Gulf to Bay access, walking distance to Bayfront Park with dog park and pickleball.
Listing Agent: Michael Yawitz (941-587-8091)
4234 GULF OF MEXICO DR #E2, LONGBOAT KEY, FL 34228
$598,000185 Days on yellowkey MLS ID: A4667654
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: Exceptional full Bay views, private beach access and kayak launch, and incredible value! 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 include hurricane-rated windows and doors, in-unit laundry, a 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
560 HARBOR POINT RD, LONGBOAT KEY, FL 34228
$9,700,000165 Days on yellowkey MLS ID: A4671218
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5245 Built: 2011Monthly Fee: $802 Tax: $46,237 (2025)Community: Bay IslesSpa: NoSingle Family
Taxes:$46,237
Remarks: Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost 200 feet of pristine waterfront, with breathtaking views of the downtown Sarasota skyline and a protected deep-water yacht slip. Deeded access to a private Gulf of Mexico beach club enhances the ultimate coastal lifestyle. Inside, the home features an exceptional floor plan with four luxurious bedroom suites and numerous entertainment spaces, including a formal living room, dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. Expansive waterfront terraces, a redesigned viewing porch, and his-and-her offices add to the home's functional elegance. Every detail has been executed to perfection, from the impeccable millwork to the finest finishes throughout. With magical views from every room, this estate embodies class, comfort, and privacy in one of Sarasota's most coveted locations. Experience refined waterfront living at its finest.
Listing Agent: Jonathan Fox, Pa (941-544-6649)
1932 HARBOURSIDE DR #254, LONGBOAT KEY, FL 34228
$585,000203 Days on yellowkey MLS ID: A4666650
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1192 Built: 1982 Tax: $6,761 (2024)Community: Fairway Bay 1Condo
Taxes:$6,761
High School: Pine View School
Remarks: Bask in breathtaking views across Sarasota Bay to the sparkling downtown skyline from this beautifully updated 2-bedroom, 2-bath condo in the exclusive, guard-gated community of Bay Isles. Offered turnkey furnished, this top-floor residence in a mid-rise five-story building combines comfort, style, and peace of mind with secure entry and 24/7 guarded access. Inside, the kitchen showcases granite countertops and rich wood cabinetry, while both bedrooms are en-suite for privacy and convenience. Lovingly maintained as a part-time vacation retreat since 1989, the condo reflects light use and thoughtful care.Fairway Bay, within Bay Isles, offers a true resort lifestyle with swimming pools, spas, tennis courts, a fitness center, and a welcoming clubhouse for social gatherings. As a Bay Isles resident, you’ll also have access to the private Bay Isles Beach Club, where you can relax on pristine Gulf shores or reserve the clubhouse for special occasions.This coveted location places you within walking distance of a marina, Publix, CVS, and local shops, while just minutes away you’ll find St. Armands Circle (5 miles), downtown Sarasota (8 miles), and all the cultural, dining, and shopping options the Gulf Coast is known for. Bay Isles is also home to 27 holes of championship golf, the world-class Tennis Gardens, the Longboat Key Moorings Marina, and two of the five acclaimed restaurants of the Longboat Key Club—where memberships are available separately. Live every day like you’re on vacation in this exceptional Gulf Coast retreat.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Beverly St Hilaire (818-416-2505)
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