Displaying: For Sale
Location: Longboat Key
Property Type(s): Single Family
Beds: 4 to 4
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Longboat Key - 41 properties found
569 BAYVIEW DR, LONGBOAT KEY, FL 34228
$4,695,000270 Days on yellowkey MLS ID: A4661312
REDUCED by $155,000 (3.2%) on 05/01/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Bayview EstatesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,064
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: New Construction. Experience the pinnacle of waterfront luxury with this brand-new construction home in the heart of Longboat Key competitively priced and ready for its next owner. Situated on a private canal, this 4-bedroom plus den, 4,106 sqft residence offers the perfect blend of modern elegance and coastal charm. Designed for seamless indoor-outdoor living, the home features two lanais, a private pool with a spa, and an elevated foundation at 9.5 feet. Boating enthusiasts will appreciate the 10,000-lb boat dock and quick access to the Gulf of Mexico for endless days on the water. Inside, enjoy engineered hardwood flooring throughout, quartz countertops in every space, and a large walk-in pantry. The thoughtfully designed layout includes two laundry rooms for added convenience. Nestled in a quiet, private setting, yet just minutes from Longboat Key’s pristine beaches, golf courses, and fine dining, this home is a rare find. Don’t miss the chance to own a waterfront masterpiece in one of Florida’s most desirable locations.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$4,695,000195 Days on yellowkey MLS ID: A4669195
REDUCED by $100,000 (2.1%) on 04/22/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Remarks: New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 4-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000174 Days on yellowkey MLS ID: A4671696
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5080 Built: 1996Monthly Fee: $208 Tax: $42,201 (2024)Community: Bay IslesSpa: YesSingle Family
Taxes:$42,201
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Rare Architectural Masterpiece on Longboat Key - Now Offered at an Exceptional New Value! Defined by its rare three-pod circular design, this sculptural residence is a dramatic composition of flowing living spaces connected by custom corridors — delivering exceptional privacy, abundant natural light, and seamless indoor–outdoor living. The Great Room pod features soaring wood-paneled ceilings and walls of glass framing tranquil water views. The circular primary suite offers a spa-level bath with dual showers, private office, lounge area, and direct pool access. The striking circular kitchen showcases a curved island beneath a two-story ceiling and skylight, with a radial appliance layout that is both artful and highly functional. Two en-suite guest bedrooms open to private patios, while a fully self-contained Secondary Primary Suite above the 32' x 23' three-car garage includes independent HVAC, a luxury bath with Steam Shower and Sauna, a flexible living space ideal for extended guests. Outdoors, enjoy protected deep sailboat water, a private dock with 12,000-lb lift, and a resort-style pool and spa. Situated behind the 24-hour gates of Bay Isles, with exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: John August (941-320-9795)
531 WEDGE LN, LONGBOAT KEY, FL 34228
$2,499,00032 Days on yellowkey MLS ID: A4687694
REDUCED by $100,999 (3.9%) on 05/01/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2751 Built: 1966Monthly Fee: $21 Tax: $10,602 (2025)Community: Country Club Shores Sec 02Spa: NoSingle Family
Taxes:$10,602
Tax Year: 2025
Remarks: A seamless blend of refined design and waterfront living defines this beautifully updated canal-front residence in Country Club Shores. Expanded from its original ranch design, the home offers approximately 2,700+ square feet of thoughtfully curated space, featuring four bedrooms, including dual primary suites on both the first and second levels—an ideal layout for guests or multi-generational living. Each bathroom is finished with timeless, elegant details that elevate the home’s overall sense of sophistication. A comprehensive 2018 renovation introduced elevated style and modern functionality, anchored by a stunning chef’s kitchen appointed with Thermador appliances, built-in refrigeration, and a generous island. Just beyond, an expansive butler’s pantry and secondary prep kitchen enhance both convenience and flow, creating an effortless environment for everyday living and entertaining. Natural light fills the interiors, drawing attention to tranquil canal views and soft glimpses of the bay from the den. The upstairs primary suite serves as a private retreat, complete with its own balcony overlooking the water—an inviting setting for quiet mornings and sunset evenings. Outdoors, a private, low-maintenance setting unfolds with a sparkling pool and beautifully updated waterfront features, including a newer dock, seawall, and 24,000 lb boat lift. Additional highlights include hurricane-impact windows and doors, classic plantation shutters, and 2022 air conditioning systems—completing this exceptional offering in one of Longboat Key’s most desirable waterfront communities. Ideally located just moments from St. Armands Circle, with its renowned dining and boutique shopping, this residence offers a lifestyle of effortless coastal sophistication.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kerry Mccarthy (720-233-7147)
515 FOREST WAY, LONGBOAT KEY, FL 34228
$1,420,000101 Days on yellowkey MLS ID: A4679679
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2880 Built: 1989Monthly Fee: $1,698 Tax: $4,802 (2025)Community: Cedars East Sec 2Spa: NoSingle Family
Taxes:$4,802
Remarks: NEW PRICE, AMAZING OPPORTUNITY!!! Experience the ultimate island lifestyle in this masterfully renovated 2,880 sqft, 4 Bed/3 Bath "lock-and-leave" condo at Cedars Tennis Resort and Club. Elevated sanctuary on the tranquil north end of Longboat Key. Offering the expansive feel of a single-family residence with the effortless "lock-and-leave" ease of being in the beautiful condo community of Cedars Tennis Resort and Club. This exquisite 4BR/3BA retreat defines coastal chic. A private elevator serves all three levels, opening into a sun-drenched great room with soaring ceilings, a fireplace, and a gourmet kitchen featuring dual islands and designer finishes. The refined dining room opens right off of this space with its custom built-in cabinetry and dry bar, ideal for any social gathering. Relax on your private, screened lanais overlooking lush tropical foliage and serene ponds, with peek-a-boo views of the Gulf. There is one on each living level. Rounding out the main living area is a versatile den/office (currently used as the 4th bedroom), a full third bathroom, beautiful hardwood floors throughout and a dedicated laundry room. The primary suite is a true oasis with a spa-inspired sunken bath, large walk-in shower, dual vanities and walk-in closets. Upstairs beyond the oasis of a primary there are two additional oversized guest bedrooms and a beautifully renovated guest bathroom with a walk-in shower. Recent updates beyond the full interior renovation include 2026 garage door replacements, and 2024 roof and AC replacement. Hardi- Board siding on exterior and Pella high-impact windows. The split 3-car garage provides total peace of mind and the rare abundance of space and storage. Nestled in the 66-acre village-like townhome community enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Cedars East is the rare community on LBK that offers shorter-term rental allowance with its 2-week minimum, making it the perfect balance for offsetting costs when not in use, without living in a hotel community. Exceptional onsite management is in place if desired. Fantastic residence, rare opportunity, come take a look today!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
6381 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$5,995,000102 Days on yellowkey MLS ID: A4678978
Bed: 4 Bath: 5.0 Gar: 9 Liv Area Sq Ft: 4224 Built: 2021 Tax: $94,565 (2025)Community: Sleepy LagoonSpa: YesSingle Family
Taxes:$94,565
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Welcome to a once-in-a-lifetime opportunity to own a sleek, modern coastal estate on one of Longboat Key’s most coveted stretches of sand. Perfectly situated on a rare double lot on the beach side of Gulf of Mexico Drive, this architectural gem incorporates uninterrupted, panoramic views of the Gulf. This completely turnkey furnished 4,420 square foot home has 4 bedrooms, 5 bathrooms and includes many upgrades showcasing incredible style. With nothing ever to be built in front, those golden sunsets and turquoise seas can be yours to savor forever. Built in 2021 with no expense spared, this home is a fortress of strength. Designed for durability by a structural architect, this home is constructed entirely of concrete utilizing sheer walls and concrete block combined with over-engineered pilings for peace of mind. Reglet trim has been achieved by utilizing metal steel framing , providing longevity and function. Inside, dramatic Euro-wall sliders blur the boundaries between indoors and outdoors, leading to a wraparound terrace that offers sweeping 260-degree views. A stunning elevated infinity-edge pool and spa, an outdoor shower and a fire table provide endless enjoyment. Level 5 drywall, oversized porcelain tile floors, and high design finishes elevate every corner. The main living level features a dazzling chef’s kitchen with European lacquer cabinetry, quartzite counters, and top-of the-line appliances: a 48” Sub-Zero fridge, 48” gas range, two ice makers, wine fridge, microwave drawer, natural gas service and more. Lutron LED lighting enhances the crisp, contemporary ambiance. The outdoor living is equally luxurious utilizing matching porcelain tile and a walnut-lined covered terrace to flow seamlessly from the interior. The top floor is a true penthouse master suite, leading to a self-contained oasis. The spa-like bathroom includes a soaking tub, a huge walk in shower and Gulf views from every room. An additional 1,150 square foot upper patio deck is framed by huge sliders allowing true indoor/outdoor living. In addition there is a second laundry room and kitchenette creating an amazing sanctuary. Whether used as a private refuge or separate guest quarters, this space can be closed off from the rest of the home, allowing the second floor, which includes 3 bedrooms and 3.5 baths, to be independently rented while preserving your own private haven. Three garages accommodate up to 9 vehicles, a gym and recreational toys. Leading outside is a large open area providing room to add a pickleball court or putting green. Beyond is over an acre of public land owned by the town of Longboat Key insuring your forever Gulf views. Additional perks include an elevator, two-zone A/C, dual laundry setups, gas tankless water heater, and electronic shades throughout. Currently operating as The Sea Grape Inn, this home offers income potential without sacrificing privacy, making it a rare hybrid of luxury retreat and smart investment. Step from your door to the sugar-white sands of Longboat Key and experience the pinnacle of Gulf-front living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
333 FIREHOUSE CT, LONGBOAT KEY, FL 34228
$2,495,000167 Days on yellowkey MLS ID: A4672573
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2900 Built: 2016Monthly Fee: $467 Tax: $10,420 (2024)Community: Conrad BeachSpa: NoSingle Family
Taxes:$10,420
Remarks: Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
610 HIBISCUS WAY, LONGBOAT KEY, FL 34228
$2,650,0005 Days on yellowkey MLS ID: A4691880
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2788 Built: 2026Monthly Fee: $78 Tax: $5,312 (2024)Community: The Preserve/LongbeachSpa: YesSingle Family
Taxes:$5,312
Remarks: Pre-Construction. To be built. Welcome to a luxurious modern retreat in The Preserve on Longboat Key. This exquisite residence boasts 4 bedrooms and 4.5 bathrooms across 2,788 square feet of impeccable design. Built with Italian flooring, cabinetry, and fixtures, the home exudes a timeless elegance. Enjoy the ultimate privacy and relaxation with a spacious primary bedroom, complemented by a spa-like ensuite. The primary wing extends its allure outdoors with a wrap-around balcony, offering panoramic views of the lush surroundings. The open-concept living spaces seamlessly blend style and functionality, creating an ideal environment for both entertaining and everyday living. The kitchen is a culinary masterpiece, featuring top-of-the-line appliances and sleek design, the sliding glass doors invite natural light to illuminate the interiors, enhancing the overall ambiance. Step outside to a meticulously landscaped yard, where outdoor living spaces beckon for gatherings or peaceful solitude. Enjoy the convenience of being just a short stroll from exceptional restaurants, upscale shopping, and breathtaking sunsets. Experience the sophisticated yet relaxed lifestyle that comes with being a resident of the North Village on Longboat Key.
Listing Agent: Rinat Sikdar (941-993-9292)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,550,000217 Days on yellowkey MLS ID: A4666688
REDUCED by $200,000 (4.2%) on 04/29/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4209 Built: 1987 Tax: $16,980 (2024)Community: Bay IslesSingle Family
Taxes:$16,980
Remarks: Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.
Listing Agent: Julie Klick (941-780-6001)
6161 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$8,995,000215 Days on yellowkey MLS ID: A4665992
1 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 4.5 Gar: 5 Liv Area Sq Ft: 4224 Built: 1997 Tax: $77,915 (2024)Community: Sleepy LagoonSpa: NoSingle Family
Taxes:$77,915
Middle School: W.D. Sugg Middle
Remarks: Under contract-accepting backup offers. Gulf front Masterpiece with Bayside Boathouse and 12klb lift Experience the pinnacle of coastal living at this unparalleled Gulf-to-Bay estate on Longboat Key, where 100 feet of private, sugar-white beachfront meets the rare luxury of a deeded bayside boathouse—a coveted feature seldom available on the island. For the discerning boater, this exceptional amenity includes a 12,000-lb lift and upgraded dockage on tranquil Sarasota Bay, allowing seamless access to open water adventures while preserving the serenity of Gulf-front living. Architecturally envisioned by Clifford M. Scholz and brought to life by Perrone Construction, the residence is a timeless fusion of coastal elegance and enduring craftsmanship. Elevated concrete block construction, a newly installed metal roof, and impact-rated windows ensure peace of mind, while expansive verandas and elevated terraces provide panoramic views of the Gulf, Bay, and captivating sunsets. Spanning three levels with elevator access from garage to top-level owner’s suite, the home’s interior is equally refined 4BR/4,224sf (7,758sf total) - anchored by a gourmet kitchen with Sub-Zero, Viking, and Neff appointments, and graced with fluid indoor-outdoor spaces designed for both grand-scale entertaining and quiet personal retreats. The primary suite is a sanctuary unto itself, featuring dual walk-in closets, spa-inspired bath, and breathtaking views of the Gulf from its private balcony. The ground level offers over 2,600 sq ft of flex space, ideal for a collector’s garage, home gym, or additional guest accommodations. Outdoors, the Gulf-front pool deck with summer kitchen invites year-round al fresco living, while a private path leads directly to one of Florida’s most pristine beaches. Perfectly positioned on North Longboat Key - near Anna Maria Island, St. Armands Circle, and downtown Sarasota, this rare estate offers absolute privacy without sacrificing access to the region’s finest dining, shopping, and cultural experiences. This is not simply a beachfront home—it is an irreplaceable legacy property offering the best of both Gulf-front tranquility and Bayfront boating. Private showings by appointment only for qualified buyers.
6489 GULFSIDE RD, LONGBOAT KEY, FL 34228
$13,995,000108 Days on yellowkey MLS ID: A4677413
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6616 Built: 2026 Tax: $42,641 (2025)Community: Sleepy LagoonSpa: YesSingle Family
Taxes:$42,641
Remarks: This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.
Listing Agent: Nicholle Mckiernan (941-928-2922)
651 BROADWAY ST, LONGBOAT KEY, FL 34228
$2,795,000163 Days on yellowkey MLS ID: A4672952
2 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3320 Built: 2003 Tax: $26,362 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$26,362
Remarks: Under contract-accepting backup offers. Experience island living at its finest in this exquisite coastal retreat in the historic Village on Longboat Key. This home offers a refined blend of relaxed coastal charm and timeless sophistication throughout more than 3,300 heated square feet. The meticulously designed interior includes elegant crown molding, coffered ceilings, custom doors, impact windows and an elevator from the garage to each level. The great room features dramatic ceiling height and opens to a large covered terrace overlooking an exceptionally private backyard, creating an ideal setting for quiet evenings and effortless entertaining. The gourmet kitchen is a chef’s dream with rich wood cabinetry, granite countertops, natural gas cooktop, a pot filler, center island with sink and second cooktop, and a bright breakfast nook that opens to a covered terrace, ideal for morning coffee. Adjacent dining and living areas flow seamlessly and are enhanced by a coffered ceiling and French doors to the charming terrace. The second-level primary suite serves as a serene retreat with polished wood floors, an intricate coffered ceiling, a comfortable seating area, and a private covered balcony for enjoying peaceful moments under the morning or evening sky. Elevated views and sound of ospreys add to the sense of tranquility. The suite also features a spacious en-suite bath with soaking tub and two walk-in closets. Three additional bedrooms provide comfort and flexibility for guests or work needs. Outdoors, a resort-style saltwater pool and spa with integrated features are surrounded by lush landscaping and generous lounging space. The expansive ground-floor lanai and outdoor kitchen further enrich the indoor-outdoor living experience. A circular brick drive accommodates more than 10 vehicles, and the oversized two-and-a-half-car garage and first-level area offer abundant storage, ideal for bicycles, golf carts, kayaks and more. The home and pool are centered on a 12,000-square-foot lot, and an adjacent 6,000-square-foot parcel is also available from the same owner for those interested in expanding or creating a larger compound. This unique golf cart friendly community is surrounded by waterfront restaurants, quaint shops, cafés, fitness centers, fishing piers, a boat ramp on Sarasota Bay, kayak launch areas and a pristine Gulf beach just moments away with no mandatory HOA. We invite you to experience this remarkable home in person to fully appreciate its beauty and lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
510 WEDGE LN, LONGBOAT KEY, FL 34228
$1,990,000206 Days on yellowkey MLS ID: A4668133
5 Days Off yellowkey (back on 4/25/2026)
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: Under contract-accepting backup offers. 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)
65 LIGHTHOUSE POINT DR, LONGBOAT KEY, FL 34228
$7,445,000140 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
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.
651 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$895,00095 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)
3598 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,795,000112 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 Agent: Roger Pettingell (941-387-1840)
5005 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$3,995,000262 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)
573 SPINNAKER LN, LONGBOAT KEY, FL 34228
$2,995,000185 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)
5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$7,800,000137 Days on yellowkey MLS ID: A4673495
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4630 Built: 2018Monthly Fee: $572 Tax: $30,971 (2024)Community: Bonaire At Longboat KeySpa: YesSingle Family
Taxes:$30,971
Remarks: Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
524 HALYARD LN, LONGBOAT KEY, FL 34228
$5,495,000248 Days on yellowkey MLS ID: A4663499
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3737 Built: 2025Monthly Fee: $21 Tax: $17,932 (2024)Community: Country Club Shores IvSpa: YesSingle Family
Taxes:$17,932
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. Only ONE BUYER will be the FIRST OWNER! Crafted by an award winning design team, this brand-new coastal contemporary waterfront residence awaits you in the exclusive Country Club Shores community on South Longboat Key. Designed for high performance and easy maintenance, this rock-solid, all block two-story residence with a private elevator provides peace of mind while capturing the essence of easy island living. A fluid open-concept layout is ideal for seamless indoor-outdoor waterfront entertaining. Soaring ceilings with impressive transom glass over casement windows and 10-foot tall sliding glass doors illuminate the interiors with natural light. At the heart of the home, a thoughtfully created gourmet kitchen and wet bar are a showpiece, featuring tailor made modern shaker doors and full panel rift-cut white oak cabinetry. Striking elements include the waterfall island and a dramatic ceiling-height hood, both wrapped in exotic natural Quartzite. A full suite of Wolf & Sub-Zero appliances includes twin 30" refrigerator & freezer towers, an 18" wine tower, under counter beverage centers, wall ovens and a contemporary gas cooktop. The first-floor primary suite is a serene retreat featuring a warm wood-slatted ceiling, expansive glass and a gorgeous bathroom with a freestanding soaking tub, dual vanities and textured porcelain tile accents. An inviting staircase leads to an elevated private home office with a half bathroom. The second floor features a game room with a wet bar and three en-suite guest bedrooms, offering comfort and flexibility complemented by a 30 foot covered balcony overlooking the tranquil water views. Energy-efficient features include variable speed 17 SEER HVAC systems, spray foam insulation and hurricane impact-resistant ES windows and doors. Control4 Smart Home technology provides many conveniences. A host of pre-wired systems—including sound, security, shades and EV charging—can be customized to the buyer's selections. Outside, a brand-new, 100-foot-long, extra-wide seawall protects a resort-style paradise! A four piece French patterned Crema Nova marble decking surrounds the 40-foot linear pool with in-water bench seating, a large sun shelf and a 12 foot wide spa. An elevated lanai with detailed ceilings features an outdoor kitchen, complete with Naturkast marine grade cabinetry, under counter refrigerator and a 42 inch built-in grill offering the perfect retreat for alfresco dining and poolside lounging. All this is just minutes from the extraordinary shopping and dining of St. Armands Circle, the cultural richness of downtown Sarasota, and the world-renowned Gulf beaches of Longboat Key. Seller is offering generous allowances towards custom closets and boat dock design providing an opportunity for the buyer to personalize these features to meet their sytle and preferences!
Listing is courtesy of: HUNT BROTHERS REALTY, INC. (941-388-7017)
Listing Agent: Rob Hunt, Jr (941-232-2431)
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