Location: Longboat Key , 34228
Do Not Show Listings
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000223 Days on yellowkey MLS ID: A4665247
Bed: 1 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1556 Built: 2025 Tax: $25,560 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$25,560
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
65 LIGHTHOUSE POINT DR, LONGBOAT KEY, FL 34228
$7,445,000135 Days on yellowkey MLS ID: A4674851
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4921 Built: 2001Monthly Fee: $617 Tax: $45,712 (2024)Community: Lighthouse PointSpa: YesSingle Family
Taxes:$45,712
High School: Booker High
Tax Year: 2024
Remarks: Longboat Key Waterfront Estate Lifestyle Unrivaled in privacy, craftsmanship, and waterfront lifestyle, this gated Lighthouse Point residence lives like a grand coastal estate, with 4 Bedrooms, 4-1/2 Baths, and nearly 5,000 square feet of refined interiors opening to sweeping terraces on two levels and serene views over a secluded, bridgeless-access lagoon leading directly to the Gulf of Mexico. Extensively renovated in 2021, the two-story Mediterranean-inspired home blends timeless architecture with a sophisticated contemporary aesthetic, framed by manicured tropical grounds on over one-third of an acre in one of Longboat Key’s most exclusive enclaves. Dramatic Arrival & Entertaining Spaces A soaring central foyer with coffered tongue-and-groove ceiling, arched French casement doors, and an elegant wraparound catwalk establishes a dramatic sense of arrival while capturing water, sky, and lush landscaping in every direction. The main living area is designed for effortless entertaining, with a sleek wood-and-stone feature wall, modern fireplace, and sculptural Tom Dixon lighting flowing through expansive glass sliders to the waterfront terrace and saltwater pool and spa. Gourmet Kitchen & Waterfront Lounge The fully reimagined Cucina Ricci kitchen serves as a chef’s workspace and social hub, with minimalist custom cabinetry, a generous island with seating, and an ultra-premium Miele VitroLine suite including double ovens, induction cooktop, and integrated coffee station. Just beyond, a waterfront lounge or media den opens directly to the covered loggia, creating a seamless indoor-outdoor living experience enhanced by an integrated Yamaha sound system for both interior and exterior zones. Owner’s Retreat & Guest Level Perfectly positioned for privacy, the main-level owner’s retreat is a secluded sanctuary with its own hallway entrance, multiple terrace access points, tray ceiling, recessed lighting, and windows on three sides framing tranquil water views. The suite is completed by dual renovated walk-in closets and a spa-inspired bath with oversized vanities, private water closet, and expansive walk-in shower with rain head, while upstairs three en suite guest suites and a mezzanine den provide luxurious accommodations and flexible space. Resort-Caliber Grounds & Boating Outside, meticulously lit landscaping, a travertine-framed saltwater pool and spa, and a private dock with 14,000 lb lift, new motors, and enhanced WiFi create a turnkey boating haven with immediate access to Sarasota Bay and the Gulf. Practical amenities include whole-house Kohler generator, hurricane protection, impact glass, large utility room with dual Sub-Zero wine refrigerators, and an oversized three-car garage with EV charger wiring. Premier Longboat Key Location Set behind the gates of Lighthouse Point, residents enjoy private tennis, a serene low-density streetscape, and a short walk to the beach. The address is just minutes from the Longboat Key Club’s golf and tennis, the boutiques and restaurants of St. Armands Circle, and the cultural attractions of downtown Sarasota. Call to Experience This Estate Schedule your private showing of this Lighthouse Point waterfront estate today to experience the scale, privacy, and curated luxury that define one of Longboat Key’s most coveted addresses. For additional details and a private tour, contact the listing agent to arrange an exclusive, by-appointment-only viewing.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
2185 GULF OF MEXICO DR #223, LONGBOAT KEY, FL 34228
$2,300,00049 Days on yellowkey MLS ID: A4685872
2 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2445 Built: 1996 Tax: $12,693 (2025)Community: Villa Di LanciaSpa: NoCondo
Taxes:$12,693
Remarks: Experience refined coastal living at Villa Di Lancia, one of Longboat Key’s favorite Gulf-front communities. This expansive three-bedroom, three-bath residence offers 2,445 Square Feet of living space paired with breathtaking Gulf and pool views and exclusive private beach access. Designed for both comfort and sophistication, the residence showcases an open floor plan enhanced by elegant crown molding throughout, rich wood doors with gold hardware, and seamless indoor-outdoor living. Sliding glass doors invite natural light while opening to a spacious private balcony—perfect for enjoying sunsets over the Gulf of Mexico and tranquil coastal breezes. The well-appointed kitchen blends functionality with timeless style, featuring granite countertops, solid white cabinetry, built-in appliances, center island with storage, pantry, and a charming breakfast/dinette area. A separate dining space flows effortlessly into the living area, creating an ideal setting for entertaining. The luxurious primary suite serves as a private retreat with balcony access, sweeping Gulf views, a spacious walk-in closet, and a spa-inspired bath complete with Jacuzzi tub, glass-enclosed shower, dual vanities, and additional storage. A guest suite with en-suite bath ensures privacy for visitors, while the third bedroom-perfect as a den or office-features French door entry and built-in workspace. Residents of Villa Di Lancia enjoy an exceptional resort-style lifestyle with guarded security, heated Gulf-side pool and spa, private deeded beach access, Har-Tru tennis courts, fitness center, and community gathering spaces. A strong, well-managed condo association with healthy reserves is a benchmark of the community. Additional conveniences include garage parking, a deeded storage unit, and beautifully maintained grounds within a gated beachfront enclave.
Listing Agent: Kim Ogilvie (941-951-6660)
842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228
$675,00029 Days on yellowkey MLS ID: A4687058
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,662
High School: None
Remarks: Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in closet and ensuite bath with dual vanities, as well as convenient in-unit laundry, covered parking and private storage closet. A combined dining and living area opens to a screened lanai and extended brick patio. This is a favorite spot for morning coffee, afternoon siestas and al fresco dining watching sunset skies. A garden gate leads to a direct side path to deeded beach access across the road. For pet owners, Bayport is small-pet friendly, and this walk-out location makes dog-walking especially easy. Spanning 27 acres of exquisitely landscaped tropical grounds, Bayport is celebrated for its timeless Tim Seibert architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The condo’s split floor plan works well for year round living or a seaside escape. A favorable rental policy offers excellent income opportunity. Located mid-key, Bayport keeps you close to shopping, daily conveniences, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise on Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rosemarie Mckee (941-504-9396)
230 SANDS POINT RD #3703, LONGBOAT KEY, FL 34228
$1,875,00030 Days on yellowkey MLS ID: A4687684
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1394 Built: 1982 Tax: $21,015 (2025)Community: Inn On The Beach Ph ICondo
Taxes:$21,015
Elementary School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Rarely available renovated corner two bedroom at The Resort at Longboat Key Club. Full gulf views from this 7th floor vantage are enjoyed from every room and the corner position offers extra square footage with extra windows. Located behind the gates of the Longboat Key Club, owners will enjoy the coastal contemporary finishes and excellent income history. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship golf, the award-winning Tennis Gardens, spa/wellness center, white sand beach with umbrellas and waitstaff and a full-service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying the Longboat Life today!
Listing Agent: Ian Addy, Pa (941-961-8850)
225 SANDS POINT RD #6103, LONGBOAT KEY, FL 34228
$539,900293 Days on yellowkey MLS ID: A4658152
REDUCED by $29,100 (5.1%) on 04/24/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $6,997 (2025)Community: Inn On The Beach Ph IiiCondo
Taxes:$6,997
Remarks: Ideal for area residents needing space for overflow guests, or for out-of-state owners who want unlimited use with the ability to still earn income! The most perfectly peaceful lagoon views are enjoyed from this first floor Junior Suite in Building 6. Unlike the other buildings, this building boasts 10' ceilings making it feel especially spacious while optimizing natural light and view. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace overlooking the turquoise lagoon water. Building 6 offers extra privacy as it is located across the street from the main entrance, but still close enough to enjoy the pool and beach without having to pack the car and drive anywhere. Updates to the residence include new washer/dryer, new dishwasher, new microwave, new glass shower doors, new commode, new closet shelving, and new fire alarm. This unit is not part of the hotel program; however, it can be rented out by the owner or a 3rd party vendor on a nightly basis. Owners can also become members of the Longboat Key Club to partake in the numerous Resort amenities (Golf, Tennis, Restaurants, Fitness Center, Marina) if they still want to enjoy the benefits of owning in a Resort community without being part of the hotel program.
651 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$895,00090 Days on yellowkey MLS ID: A4680514
REDUCED by $30,000 (3.2%) on 04/24/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2242 Built: 1974 Tax: $18,621 (2024)Community: Longboat KeySingle Family
Taxes:$18,621
Remarks: PRICE IMPROVEMENT!! Canal-front 3-bedroom, 2-bath home with an attached 1-bedroom, 1-bath apartment above the garage with private entrance, offering 2,242 square feet of total living space. The property has completed remediation and is ready to be rebuilt to suit your needs. Features include high ceilings, a 2-car garage, and a generous ¼-acre lot. Canal offers direct access to Sarasota Bay with no bridges. Conveniently located minutes from marinas, dining, and shopping, with easy access to St. Armands Circle, downtown Sarasota, and Anna Maria Island. Bring your personal touch to recreate this gem or start new and build the home you've always wanted on this 124 ft wide lot. A property with exceptional location and potential.
Listing is courtesy of: ALLEGIANT REAL ESTATE GROUP (941-685-3958)
Listing Agent: Lori Campbell (941-685-3958)
4400 EXETER DR #305, LONGBOAT KEY, FL 34228
$324,9006 Days on yellowkey MLS ID: A4691085
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 837 Built: 1970 Tax: $2,819 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$2,819
Remarks: Welcome to coastal living on coveted Longboat Key. Priced to move, this beautifully maintained 1-bedroom residence at 4400 Exeter Dr Unit 305J offers an exceptional opportunity to own in one of the island’s most desirable waterfront communities. Inside, you’ll find a bright open floor plan with warm wood flooring, an updated kitchen featuring stone countertops, stainless appliances, breakfast bar seating, and abundant custom storage. The spacious living area flows seamlessly to the enclosed lanai where tranquil water and tropical garden views create the perfect setting for morning coffee or evening relaxation. The generous primary suite includes large windows, great natural light, and access to a beautifully updated bath with dual vanities and modern finishes. Enjoy resort-style amenities including waterfront grounds, boat docks, pool, lush landscaping, and close proximity to deeded beach access, golf, tennis, dining, and shopping. Whether you’re seeking a seasonal retreat, investment property, or year-round island lifestyle, this value-priced Longboat Key residence is ready for immediate enjoyment. Opportunities at this price on Longboat Key do not last. Schedule your private showing today.
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
6700 GULF OF MEXICO DR #121, LONGBOAT KEY, FL 34228
$435,0007 Days on yellowkey MLS ID: TB8500916
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 936 Built: 1969 Tax: $5,653 (2025)Community: Whitney BeachCondo
Taxes:$5,653
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Best elevated water view in complex …fully renovated with mid-century classic furniture…a must see tranquil spot to see dolphin and manatee. Uncrowded beautiful beach …pool…walk to 3 great restaurants.
Listing is courtesy of: LISTED SIMPLY (800-995-5879)
Listing Agent: Sinan Zakaria (800-995-5879)
2165 GULF OF MEXICO DR #115, LONGBOAT KEY, FL 34228
$2,350,00060 Days on yellowkey MLS ID: A4684194
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2485 Built: 1996 Tax: $12,382 (2025)Community: Villa Di Lancia Ph 1Condo
Taxes:$12,382
Remarks: Experience and enjoy breathtaking, unobstructed Gulf views from this exceptional “walk-down” corner 3-bedroom 3-bath residence in the prestigious Villa Di Lancia community on South Longboat Key. Fully updated and spanning 2,485 sq. ft., this residence feels like its own private beachfront home. Upon entering from the semi-private elevator lobby, you are welcomed into an open and light-filled floor plan with soaring 10-foot ceilings and expansive walls of glass. As one of the most desirable corner residences in the community, this residence showcases panoramic Gulf views from nearly every room, which can be enjoyed by an additional wall of windows that flood the interior with natural light. The expansive great room connects to a nearly 500 sq. ft. covered terrace — your front-row seat to spectacular sunsets over turquoise waters! The terrace also has a private staircase allowing direct access to the beach and Gulf-front pool and spa, creating a rare and seamless indoor-outdoor lifestyle. The updated eat-in kitchen features a serving bar, walk-in pantry, full laundry room, and generous storage. The split floor plan allows owners and guests alike to enjoy quiet privacy. The primary suite is a true retreat, complete with direct Gulf views, private terrace access, spacious closets, and a large en-suite bath. The guest wing includes a second en-suite bedroom, as well as a third bedroom or a convenient and flexible den space with an adjacent bath. Villa Di Lancia is an exclusive boutique community with only 38 residences with resort-style amenities. Relax by the heated Gulf-front pool and spa, or enjoy friendly competition on the Har-Tru tennis and pickleball courts, as well as a state-of-the-art fitness center and steam room. Resort-style living has been effortlessly achieved throughout the community, including the newly updated clubhouse, social room and kitchen, on-site management, 24-hour manned gate, EV charging station, secure under-building parking, guest parking, and a private storage room. This welcoming community is both pet-friendly and impeccably maintained. Ideally located on the southern end of Longboat Key, residents enjoy proximity to fine and casual dining, golf, marinas, shopping, St. Armands Circle, and Sarasota’s cultural attractions. Residences here are rarely available. This is a rare opportunity to own a luxurious beachfront sanctuary and experience refined coastal living at its finest. This residence feels like a beautiful private home on the beach!
Listing Agent: Judy Kepecz-Hays (941-587-1700)
6330 LAGUNA DR, LONGBOAT KEY, FL 34228
$1,999,989162 Days on yellowkey MLS ID: A4672554
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2856 Built: 2002Monthly Fee: $542 Tax: $18,656 (2023)Community: Laguna Yacht VillageSingle Family
Taxes:$18,656
Tax Year: 2023
Remarks: Modern Beach Home priced aggressively to sell as the owners are relocating. Ocean Views! Private Dock With Boat Lift On The Bay! Exclusive Beach Community, The Ultimate Beach lifestyle! This raised (16ft.), three bedroom (possible 4th), three bath, three plus car garage home is situated perfectly between the gulf and bay. The exclusive, gated community of Laguna Yacht Village is Longboat Key's best kept secret, consisting of only 8 homes on 9 lots. This quiet, private beach and boating development is unmatched! Relax on your deck, on your boat, at the beach or by the private heated and chilled pool in the knowledge that all the grounds, pool and dock infrastructure are maintained by the HOA. The home has been thoroughly modernized and expanded in 2019/2020 by the current owners. New 25 year aluminum roof, pre-painted hardiplank exterior, enclosed upper deck expanded Master Suite, complete bathroom and kitchen renovations, new water heater (2025), 5 ton HVAC, washer, dryer and kitchen appliances (Sub Zero and Bosch) as well as refinished hardwood floors on the main level and newly laid matching hardwood floors throughout the entire upstairs make this effectively a totally new home. Whilst not required by the current owners, the upstairs loft area could easily be converted into a 4th bedroom. The majority of the work was accomplished by Greyhawk of Bradenton. Other lavish touches include new solid panel doors, new 16 feet wide opening glass slider doors, integrated 180 bottle wine fridge, an oversized 3 plus car garage including new door and the installation of a 10,000 lb boat lift at the deeded private dock. Call today to schedule your private Viewing.
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Zachary Kaplan (941-321-6796)
3598 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,795,000107 Days on yellowkey MLS ID: A4677923
1 Days Off yellowkey (back on 4/18/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3417 Built: 1996Monthly Fee: $833 Tax: $15,229 (2025)Community: Queens HarbourSpa: NoSingle Family
Taxes:$15,229
Remarks: Situated within the gated Queens Harbour enclave of Bay Isles, this thoughtfully updated four-bedroom courtyard residence offers a refined blend of privacy, comfort, and waterfront living on Longboat Key. Designed around a lush central courtyard, the home creates an effortless indoor-outdoor flow anchored by a resurfaced swimming pool and new paver deck—an inviting retreat for everyday living or entertaining. A private cabana suite with its own entrance provides flexibility for guests or extended stays, enhancing the home’s functionality while maintaining separation from the main living areas. Entry begins through custom mahogany and glass double doors, opening to a reimagined open-concept interior with soaring 14-foot ceilings, wide-plank wood flooring, and carefully curated architectural detail throughout. The great room is centered around a travertine-encased electric fireplace and framed by walls of windows and glass sliders that capture tranquil lake views and abundant natural light. This space flows seamlessly into the formal dining area, highlighted by a statement chandelier and tongue-and-groove tray ceiling, and continues into the chef’s kitchen—designed as the heart of the home. The kitchen features a dramatic 14-foot quartz-topped island, custom designer cabinetry by Sarasota Architectural Woodworking, and newer Thermador appliances, including a five-burner gas cooktop, dual built-in ovens, pull-out pantry cabinetry, and a 48-inch stainless sink. Adjacent informal dining and family spaces include aquarium-style glass windows and an oversized wet bar with a full-size wine cooler capable of storing over 100 bottles. The primary suite, located on the main level, offers a peaceful lakefront setting with French-door access to the patio, custom built-in storage, and a walk-in closet. The spa-inspired bath was recently updated with dual quartz-topped walnut vanities, soaking tub, glass-and-stone shower, and private water closet. Also on the first floor are a versatile study overlooking the courtyard and a bonus room with an attached full bath that can serve as an additional bedroom or media space. The second level is dedicated to a private en-suite guest bedroom. Queens Harbour residents enjoy access to a heated Olympic-size pool and spa, along with deeded entry to the private Bay Isles Beach Club. Beyond the gates, Longboat Key’s lifestyle amenities are just minutes away, including the Longboat Key Club’s golf and tennis facilities, marinas, dining, and everyday conveniences. St. Armands Circle and downtown Sarasota’s cultural attractions—shopping, galleries, theaters, and waterfront dining—are easily accessible, completing the appeal of this well-positioned coastal residence.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
605 SUTTON PL #102, LONGBOAT KEY, FL 34228
$485,00083 Days on yellowkey MLS ID: A4681310
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 992 Built: 1973Monthly Fee: $1,642 Tax: $6,934 (2024)Community: Sutton PlaceCondo
Taxes:$6,934
Remarks: Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place boasts two heated swimming pools, fishing pier and game room, complete with billiards and ping-pong; along with a fitness center and clubhouse. Deeded beach access is located directly across the street.
5005 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$3,995,000257 Days on yellowkey MLS ID: A4661988
2 Days Off yellowkey (back on 4/23/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4044 Built: 2018Monthly Fee: $766 Tax: $49,274 (2024)Community: BonaireSpa: YesSingle Family
Taxes:$49,274
Remarks: Under contract-accepting backup offers. The Quintessence of Coastal Living: A British West Indies Masterpiece on Longboat Key - Where Architecture Meets Paradise. Offered turn-key, this exquisite 4,000+ sq. ft., 4-bedroom, 4.5-bath residence in Longboat Key’s prestigious Bonaire subdivision is a rare union of refined British West Indies architecture and the serene beauty of Florida’s Gulf Coast. Every inch of this home has been thoughtfully crafted to evoke a sense of effortless luxury—where sun-kissed days and gentle Gulf breezes blur the line between indoors and out. From the moment you step through the grand entrance, you’re embraced by light, texture, and tranquility. Creamy finishes, warm woods, and bespoke millwork elevate every space, while expansive windows and French doors invite in the turquoise glow of the Gulf and the soothing rhythm of coastal life. Main Level Elegance - The heart of the home features an open-concept chef’s kitchen with top-of-the-line appliances: a Wolf 6-burner gas range with custom vent hood, dual Asko dishwashers, Sub-Zero refrigerator/freezer, Wolf convection/microwave, and a 50-bottle wine captain. Quartz countertops, artisan pendant lighting, and a massive island with farmhouse sink make this space as beautiful as it is functional. The adjoining dining and great room flow effortlessly to an expansive balcony - perfect for indoor-outdoor entertaining. The main-floor Primary Suite offers tray ceilings, shiplap accents, dual walk-in closets, and a spa-inspired bath with soaking tub, double-entry stone shower, and sparkling stone vanities. Two additional ensuite guest rooms on this level echo the home’s airy, coastal elegance, and exceptional quality. Upper-Level Retreat - Ascend to a private owner’s sanctuary with dual custom closets and a lavish bath adorned with blue calcite counters, glass mosaic tile, and a freestanding tub. This level includes a substantial private balcony with access to the upper-level viewing balcony. The Observation Deck - Crowning the home is the ultimate vantage point—a “Sunset Terrace ” with panoramic Gulf and Sarasota Bay views. It’s here you’ll end each day watching sunsets paint the horizon in unforgettable color. Resort-Style Outdoor Living - The pool retreat is an absolute showstopper - pocketing sliding doors reveal coral stone terraces, a resort-style pool with sun shelf and tiled cocktail table, a 10-person spa, and a fully equipped outdoor kitchen with seating for eight. The entire area is lined with an automatic insect elimination system to ensure you can enjoy the outdoors all year long. Optical lighting enhances the overflowing water features which seem to dance in the glow of firelight, creating the perfect setting for stargazing or nightcaps. The community provides private beach access and is close to world-class golf, tennis, fine dining, and the largest deep-water marina on the Gulf coast. This is more than a home - it’s a sanctuary, a work of art, and a lifestyle. Delivered exactly as you see it, fully furnished and ready to enjoy, this British West Indies masterpiece awaits the one discerning buyer ready to claim the very best of Longboat Key coastal living.
Listing Agent: Kathy Callahan (941-900-8088)
2425 GULF OF MEXICO DR #10F, LONGBOAT KEY, FL 34228
$1,495,000296 Days on yellowkey MLS ID: A4656887
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1973 Tax: $14,482 (2024)Community: Sea Gate ClubSpa: NoCondo
Taxes:$14,482
Remarks: Gulf-Front Elegance | Sea Gate Club #10F | Longboat Key —Welcome to Sea Gate Club #10F, a rarely available 10th-floor end unit offering spectacular, front-row Gulf views in one of Longboat Key’s most intimate beachfront communities. Perfectly positioned mid-island along the sandy shores of the Gulf of Mexico, this elegant 2-bedroom, 2-bath residence captures direct, unobstructed views of the turquoise waters and mesmerizing sunsets from nearly every room. As a corner unit, it’s bathed in natural light and offers enhanced sight lines—creating a bright, open, and serene coastal retreat. Step onto your private balcony and take in over 350 feet of secluded beachfront, where dolphins, manatees, and colorful marine life glide through the waves just beyond your door. Inside, you’ll find a blend of comfort and coastal sophistication, ideal for relaxing or entertaining. Sea Gate Club is a boutique community of just 89 residences spread across 15 stories, offering a uniquely quiet and refined lifestyle. The building has undergone major capital improvements in recent years, including impact-rated windows (2021), a full exterior restucco and repaint (2022), a new roof (2023), and upgrades to the pool, spa, and elevator doors. Additional enhancements are already in motion, with a new AC tower coming in 2025 and a sun deck scheduled for completion in Summer 2025—all fully paid for by current owners, totaling over $100K/unit. Residents enjoy resort-style amenities including a Gulf-front pool and hot tub, fitness center, clay tennis court, library, and a social room with catering kitchen. Shaded tiki huts, outdoor showers, and climate-controlled storage for bikes, kayaks, and paddleboards complete the experience of true beachfront living. Ideally located, Sea Gate places you just steps from Publix, CVS, and Bayfront Park, where you’ll find pickleball, tennis, shuffleboard, a playground, and kayak launch. Boaters will appreciate proximity to Longboat Key Moorings and nearby marinas, while St. Armands Circle—just three miles away—offers an upscale mix of dining, boutique shopping, and laid-back coastal charm. Here, you truly get the best of both worlds: to the north, the natural beauty of Anna Maria Island, and to the south, the vibrant arts, culture, and dining of downtown Sarasota. Whether you’re soaking in sunset views from your balcony or exploring nearby island attractions, every day feels like a vacation. This is Gulf-front living at its finest—private, peaceful, and rarely available. Schedule your private showing today and claim your slice of Longboat Key paradise.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Erica Thomas, Llc (941-799-9365)
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,700,00043 Days on yellowkey MLS ID: A4686539
1 Days Off yellowkey (back on 4/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $13,728 (2025)Community: Sea Gate ClubSpa: YesCondo
Taxes:$13,728
High School: Riverview High
Remarks: Under contract-accepting backup offers. Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
573 SPINNAKER LN, LONGBOAT KEY, FL 34228
$2,995,000180 Days on yellowkey MLS ID: A4668083
0 Days Off yellowkey (back on 4/23/2026)
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3926 Built: 1998Monthly Fee: $8 Tax: $17,104 (2024)Community: Country Club Shores Sec 02Spa: NoSingle Family
Taxes:$17,104
Remarks: Under contract-accepting backup offers. Perfectly positioned on a quiet cul-de-sac at the preferred south end of Longboat Key, this 4BR/5BA waterfront residence spans nearly 4,000 sq. ft. of beautifully designed living space just one lot from the open bay. The paver drive and lush landscaping create a gracious welcome to a home filled with natural light, soaring ceilings, and elegant architectural details. Expansive living areas flow seamlessly between spaces, featuring tile flooring, tray-accented ceilings, recessed lighting, and walls of glass framing tranquil water views. The open kitchen is ideal for entertaining, with stone countertops, white cabinetry with glass-panel accents, a breakfast bar, and direct access to the adjoining dining and living areas. The first-floor primary suite is a serene retreat, complete with rich wood floors, a spacious custom closet, pool access, and a luxurious bath with dual vanities, spa tub, and glass-enclosed shower. Upstairs, guest suites each offer en-suite baths for privacy and comfort. Outdoors, enjoy the resort-style pool surrounded by tropical landscaping and covered sitting areas. A private dock with 10,000-lb lift and seawall makes this a true boater’s paradise on a deepwater canal. Additional highlights include impact glass throughout and an oversized 3-car garage. Residents of Country Club Shores enjoy deeded beach access and the option to join the prestigious Longboat Key Club, offering 45 holes of championship golf, world-class tennis, a full-service marina, beachfront dining, fitness and spa facilities. All just minutes from St. Armands Circle and downtown Sarasota.
Listing Agent: Bruce Myer (941-376-5311)
4955 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$5,650,00043 Days on yellowkey MLS ID: A4686511
0 Days Off yellowkey (back on 4/13/2026)
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
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
1241 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$950,00061 Days on yellowkey MLS ID: A4684166
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 940 Built: 1996 Tax: $8,141 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$8,141
Remarks: This unique plaza level Water Club residence offers you the convenience of stepping out to the exceptional Water Club amenities and lush grounds that lead to the sandy beach and azure waters of the Gulf of Mexico without the use of an elevator. This spacious 1 bedroom special residence features high 10 foot ceilings and the openness is enhanced by the floor to ceiling windows that captivate the tropical Florida landscaping. This home feels and lives like a beach house and sliding glass doors opening to the terrace complement this feeling by extending the living space to the outdoors and the serene setting. The indoor space is open and flows seamlessly from the living room area to kitchen space which also has a separate eating area open to the balcony and outdoors. The kitchen has granite countertops and high end cabinets and is designed to accommodate the joys of cooking. The floor plan offers privacy for the spacious master suite with a private terrace, elegant master bath and walk-in closet with a dressing area. There is also generous storage area in the condo. The Water Club is a premier Gulf front condominium with exceptional amenities and services. The designer decorated Club House features a professionally equipped gym and his and her spa areas, wine storage, billiard room, library, sunset bar plus a grand ballroom for special and formal occasions and gourmet catering kitchen. When not enjoying the beach, there is a heated elevated beautiful pool and hot tub with plenty of seating plus 4 Har-tru tennis courts. This condo location can also be used as a guest suite to be enjoyed by family and guests. The Water Club is conveniently located just minutes from award winning restaurants, Publix and CVS, St. Armands Circle, downtown Sarasota plus the Longboat Key Club for golf, tennis and restaurants is also nearby.
4995 GULF OF MEXICO DR #500, LONGBOAT KEY, FL 34228
$5,895,000106 Days on yellowkey MLS ID: A4677613
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3344 Built: 2007 Tax: $47,519 (2024)Community: PositanoSpa: NoCondo
Taxes:$47,519
Remarks: Step right into the epitome of Florida beachfront luxury with this stunning first-floor Capri unit on Longboat Key. Nestled within the exclusive Positano community—an intimate 10-acre oasis of just 29 residences—this condo offers a seamless walkout straight to the pristine beach and the azure waters of the Gulf of Mexico. This is Florida living at its finest. The condo features a fantastic wrap-around terrace on the Gulf side, perfect for soaking in the outdoor splendor from morning coffee to sunset cocktails. The primary suite offers direct steps down to the private community pool, while additional terraces off the secondary bedrooms ensure both privacy and gorgeous views. Spanning a generous 3,343 square feet, this true three-bedroom, all en-suite residence boasts a Gulf-front gourmet kitchen with state-of-the-art appliances, an adjacent family gathering area, and an open-plan flow from the living room to the dining space. Floor-to-ceiling windows frame dramatic views of the Gulf and the beach, while beautiful porcelain tile floors, 10-foot ceilings, and crown molding add to the sense of refined elegance. You'll enjoy the convenience of a private, enclosed two-car garage and the exceptional amenities of the owner's club, including a state-of-the-art fitness center, catering kitchen, and a lounge with a fireplace, plasma TV, and surround sound. Outdoors, there's a 75-foot Olympic pool, spa, grilling area, and shaded cabanas, all set amidst lush tropical landscaping. Truly, this condo is as close to the beach as it gets on Longboat Key.
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