Displaying: For Sale
Location: Longboat Key
Property Type(s): Single Family
Beds: 4 to 4
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Longboat Key - 40 properties found
3271 BAYOU RD, LONGBOAT KEY, FL 34228
$1,995,00019 Days on yellowkey MLS ID: TB8515918
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3059 Built: 2014Monthly Fee: $104 Tax: $27,748 (2025)Community: Bay IslesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$27,748
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Nestled behind the gates of prestigious Bay Isles on Longboat Key, this exceptional residence offers over 3,000 square feet of thoughtfully designed living space surrounded by lush tropical landscaping and just moments from the Gulf of Mexico. Combining timeless architecture, spacious interiors, and resort-style outdoor living, this home delivers the privacy and elegance that define the Longboat Key lifestyle. A grand entry welcomes you into an open and inviting floor plan featuring soaring ceilings, abundant natural light, and generous living and entertaining spaces. The expansive great room flows seamlessly into the dining area and well-appointed kitchen, complete with ample cabinetry, extensive counter space, and a convenient wet bar for effortless entertaining. The first-floor primary suite serves as a private retreat with a spacious bedroom, large walk-in closet, and luxurious en-suite bath. Additional guest bedrooms are thoughtfully positioned for privacy and comfort, while the second floor offers a private guest suite with balcony access—perfect for visitors seeking their own space and enjoying tropical views. Designed for year-round enjoyment, the screened outdoor living area is a true highlight. Relax poolside in the sparkling heated pool and spa, entertain under the covered lanai, or unwind amidst the lush tropical surroundings that create a secluded backyard oasis. Located within the highly sought-after Bay Isles community, residents enjoy 24-hour gated security, beautifully maintained grounds, and exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Just minutes away are the Longboat Key Club's championship golf courses, tennis facilities, marina, waterfront dining, boutique shopping, and renowned St. Armands Circle. Offering the perfect blend of luxury, privacy, and coastal convenience, this exceptional Longboat Key residence presents a rare opportunity to enjoy one of Sarasota's most desirable island lifestyles.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Robert Johnson (813-364-2250)
635 MARBURY LN, LONGBOAT KEY, FL 34228
$1,945,000134 Days on yellowkey MLS ID: A4681616
2 Days Off yellowkey (back on 6/8/2026)
REDUCED by $50,000 (2.5%) on 04/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2446 Built: 1958 Tax: $22,205 (2024)Community: Sleepy Lagoon Park 2Spa: YesSingle Family
Taxes:$22,205
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. Come savor laid-back luxury and the island lifestyle that Longboat Key is known for in this tranquil, seaside retreat. AND listed more than $100,000. under a current appraisal! This home is a decorators dream! Completely remodeled with a brand new kitchen, all new flooring, 4 bedrooms and 3 baths in an open and inviting space. The line is blurred between indoor and outdoor living with a gorgeous sparkling pool just beyond the mahogany French doors, surrounded by tropical plants and situated on a fabulous canal. For the boaters, you have a 14,000 lb. lift and no fixed bridges to the Gulf of Mexico, making your day on the water an easy experience. Nightly sunsets at the neighborhood beach is just a short walk away and something to make a regular habit of! A short distance to multiple restaurants, shopping, 12 miles of biking paths, and the incredible Joan Durante Park on the Bay only add to the remarkable quality of life living on an island can provide. When you’re ready for something more, St.Armands Circle and the cultural mecca of Downtown Sarasota is just a short drive away. This extraordinary home is a true island paradise you must come see.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
548 HORNBLOWER LN, LONGBOAT KEY, FL 34228
$4,950,000253 Days on yellowkey MLS ID: A4668463
1 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3976 Built: 2015Monthly Fee: $8 Tax: $47,046 (2024)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$47,046
Remarks: Under contract-accepting backup offers. This exquisite home is sure to exceed expectations! This exceptional 4 bed/5 bath canal-front estate is located in coveted Country Club Shores, where chic architecture, thoughtful craftsmanship, and effortless coastal luxury converge. Designed by DSDG architects to maximize the contemporary sightlines and southern exposure, this Voight built custom residence offers a spectacular open floor plan and is positioned just three lots from the open waters of Sarasota Bay. This extraordinary residence is better-than-new with a recently installed metal roof, AC systems, and whole home generator and has been impeccably maintained. The home has been built to effortlessly withstand the Florida coastal environment while maintaining its magnificent beauty and clean lines. Boaters will appreciate the Trex dock equipped with a 20,000-lb boat lift, kayak and paddleboard racks, and convenient launch deck - providing quick, easy access to bay and Gulf waters. Inside, the home is both stunning and impressive with exquisite finishings and custom millwork. The first-floor owner’s suite is a luxurious retreat highlighted by soaring triple-coffered tray ceilings, tranquil views, and private pool access for a midnight swim. The spa-like bathroom is pure luxury. The chef’s kitchen is a true showpiece, featuring Viking appliances, a Sub-Zero Pro refrigerator, a walk-in pantry, expansive countertops, and a dramatic 14-foot quartz island perfect for large gatherings. The integrated dining area is framed by an aquarium window which emphasizes the tranquil water views. The family room is a natural extension of the kitchen and provides a generous area with direct access to the lanai, grille and dining areas and is perfect for enjoying movies, or just gathering with friends and family. The great room is spacious with large archways, gas fireplace, custom built-in shelving, and coffered shiplap ceilings which add to the drama of this cozy but elegant space. A wall of windows provides access to the covered lanai area and expands the feeling of openness highlighting the pool, sparkling spa, and water views. The second floor has been completely reimagined to elevate both style and function, offering three private guest suites, a versatile and spacious Florida room, wet bar, and a 300+ bottle state-of-the-art walk-in wine cellar. The enclosed upper lanai enhances ambiance and panoramic views. The Florida room provides a flexible space for enjoying sporting events or wine tastings, and includes a full bath for convenience. The 3 bedrooms on the second level are generous in size and 2 of the 3 include ensuite baths. Outdoor living is equally exceptional. The lanai with a Cypress-clad ceiling includes a new grill and dining area and pool bath, which steps down to the saltwater pool, spa, and sun deck - an ideal setting for entertaining or enjoying sunshine year-round. Additional features include a two-car garage with generous overhead storage, a rear enclosed storage compartment, and an electric vehicle charger. There is ample vertical height in the garage to add a car lift as an option. Residents of Country Club Shores enjoy private deeded beach access to the Gulf of Mexico, with optional golf and tennis memberships available at the nearby Resort at the Longboat Key Club. This is waterfront living at its finest - refined, relaxed, and designed to be enjoyed. A must-see property to fully appreciate the exceptional lifestyle, upgrades, and craftsmanship throughout.
Listing Agent: Kathy Callahan (941-900-8088)
6322 LAGUNA DR #1, LONGBOAT KEY, FL 34228
$2,499,900243 Days on yellowkey MLS ID: A4669170
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2886 Built: 2001 Tax: $12,100 (2024)Community: Laguna Yacht Village A CondoSpa: YesSingle Family
Taxes:$12,100
Remarks: Welcome to Laguna Yacht Village on beautiful Longboat Key- a gated waterfront community located across the street from the beach, with private bay access. This fully furnished turnkey home is perfectly positioned to embrace the island lifestyle, with fantastic gulf views from almost every room. The home includes a deeded deep-water dock (Slip #6- boat lift included), located in a protected lagoon just minutes from the Intracoastal Waterway and Gulf of Mexico with no fixed bridges, making it a boater’s dream. This modern Key West inspired three story single residence with an oversized 3-car garage features four bedrooms, three full baths, and over 2,886 square feet of beautifully designed living space. Perfectly positioned to embrace the island lifestyle, this home includes a deeded deep-water dock (Slip #6) located in a protected lagoon just minutes from the Intracoastal Waterway and Gulf of Mexico — with no fixed bridges, making it a boater’s dream. Step inside and experience a harmonious blend of coastal elegance and comfort. Expansive living areas feature soaring ceilings, an abundance of natural light, and sophisticated finishes throughout. The culinary-inspired kitchen, designed in timeless style, boasts custom cabinetry, quartz countertops, and an oversized central island — the ideal space for hosting and entertaining. The primary suite, complete with a study, serves as a serene retreat with dual vanities, a hydro-massage soaking tub, and a walk-in glass-enclosed shower for the ultimate spa-like experience. Multiple balconies, including an elevated screened patio off the main level, provide refreshing sea breezes and captivating water views of the Gulf. A ground-floor patio further extends the outdoor living experience. The oversized garage provides ample storage for beach gear and boating essentials. The gated community features a resort-style pool offering a true lock-and-leave lifestyle. Residents will appreciate convenient proximity to Longboat Key’s pristine beach, award-winning island restaurants, boutique shopping, and parks — all while being a short drive from the cultural heart of downtown Sarasota and St. Armands Circle.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Brandy Loebker (941-404-4737)
523 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$1,895,00032 Days on yellowkey MLS ID: A4694601
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2899 Built: 2002 Tax: $20,291 (2025)Community: Sleepy Lagoon ParkSingle Family
Taxes:$20,291
Elementary School: None
High School: None
Middle School: None
Remarks: This beautifully reimagined John Cannon home, in the tranquil north end of Longboat Key, blends luxury with island living. The custom, Spanish-style design offers four bedrooms and a complete top-to-bottom renovation. New hurricane-rated windows and doors ensure safety, and two brand-new air conditioning units—still under warranty—keep you cool. A tankless water heater, just three years old, provides endless hot water. In the garage, there’s a Mitsubishi AC dehumidifier, and the roof was replaced in 2026, giving you peace of mind. The kitchen is fully outfitted with Wolf and Sub-Zero appliances, and every bathroom has been completely remodeled. You’ll find extra storage in the garage, and deeded beach access means the sand is just moments away. Beyond the home, the location is unbeatable. You’re right across from the island’s pristine white sand beaches and close to golf, tennis, and the Longboat Key Club. You’re also a short drive from Anna Maria’s restaurants and bars. And if you love the outdoors, you can paddleboard, boat, kayak, and enjoy the island’s abundant wildlife—all right at your doorstep. This home offers both elegance and adventure, all in one stunning package.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$7,495,000188 Days on yellowkey MLS ID: A4673495
REDUCED by $305,000 (3.9%) on 05/08/2026
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. Walk in to this fully furnished home which is 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.
651 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$845,000146 Days on yellowkey MLS ID: A4680514
REDUCED by $50,000 (5.6%) on 06/03/2026
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)
761 NORTON ST, LONGBOAT KEY, FL 34228
$4,290,000153 Days on yellowkey MLS ID: A4677200
REDUCED by $100,000 (2.3%) on 05/30/2026
Bed: 4 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 4674 Built: 2004 Tax: $14,281 (2024)Community: Sleepy Lagoon Park 2Spa: YesSingle Family
Taxes:$14,281
Remarks: NOW OFFERED WITH A SIGNIFICANT PRICE IMPROVEMENT, 761 Norton Street presents an exceptional opportunity to own a luxury waterfront home in Longboat Key's highly desirable Sleepy Lagoon community. Positioned along a quiet canal with direct boating access to Sarasota Bay, the Intracoastal Waterway, and the Gulf, this canal-front residence combines the durability of reinforced concrete construction with the relaxed sophistication of Florida waterfront living. Featuring four bedrooms, four full en-suite baths, three half baths, and 4,674 square feet under air, the residence was thoughtfully designed to accommodate multi-generational living, extended family visits, seasonal guests, or those seeking exceptional flexibility for entertaining. Built with enduring quality in mind, the home features solid poured concrete construction reinforced with rebar throughout, hurricane-rated windows and doors, and a five-stop elevator providing convenient access to every level. A light-filled travertine foyer with an interior water feature creates a memorable arrival, while smart-home technology and newly installed remote-controlled blinds add modern convenience throughout. The main living level centers around an open-concept kitchen and gathering space designed for effortless indoor-outdoor living. Custom wood cabinetry, stainless steel KitchenAid appliances, a cooktop, beverage cooler, and generous entertaining areas flow seamlessly to the outdoor terrace. Beyond the walls of glass, a private resort-style environment awaits. The travertine pool deck features an infinity-edge pool and spa, outdoor shower, summer kitchen, and Coyote grill, creating an ideal setting for waterfront entertaining and year-round enjoyment. For boating enthusiasts, the property's canal-front setting is among its most compelling features. A 28,000-pound boat lift and dedicated lift for two personal watercraft provide convenient access to the region's renowned boating waters, allowing owners to cruise directly to waterfront restaurants, explore Sarasota Bay, spend the day fishing, or enjoy sunset excursions throughout Longboat Key and Sarasota's barrier islands. Inside, architectural details add warmth and character, including a two-tone tray ceiling, travertine fireplace, custom art niches, and generously sized guest suites with walk-in closets and private baths. One suite features a Jacuzzi tub, dual vanities, walk-in shower, and private water closet with bidet, while additional suites provide comfortable accommodations for family and guests. A rare and distinctive feature of the residence is its mirrored floor plan concept, creating two separate yet connected living experiences under one roof. An additional living level includes a second kitchen, bar area, living room, and matching guest accommodations, offering remarkable flexibility for private guest quarters, extended family living, or long-term visitors. Additional highlights include a 4-car tandem garage, abundant storage, and a premier location on Longboat Key. Residents enjoy convenient access to St. Armand's Circle, the St. Regis Longboat Key Resort, downtown Sarasota, Anna Maria Island, championship golf, world-class dining, boutique shopping, and the area's renowned Gulf beaches. Combining direct boating access, exceptional construction quality, resort-inspired outdoor living, and a coveted Longboat Key location, 761 Norton Street represents a rare opportunity to experience the very best of Florida waterfront living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
595 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$3,140,000250 Days on yellowkey MLS ID: A4668868
REDUCED by $35,000 (1.1%) on 05/29/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1966Monthly Fee: $21 Tax: $26,814 (2025)Community: Country Club ShoresSingle Family
Taxes:$26,814
Remarks: Longboat Key Waterfront Perfection! Experience the ultimate coastal lifestyle in this 4-bedroom, 2.5-bath home, effective year 2016, in the prestigious Country Club Shores community—just three homes from Sarasota Bay with quick access to the Gulf of Mexico. Boater’s paradise with two boat lifts (20,000 lb and 7,000 lb), a new seawall, and private dock complete with a custom fish cleaning station (all 2022–2023). Completely remodeled twice in the last few years, this home blends elegant design and high-end engineering: roof, plumbing, electrical, and PGT hurricane-impact sliding doors and windows throughout, 2 new A/C's 2024. The flowing open-concept floor plan extends to a resort-style outdoor area through retractable glass walls, revealing a heated pool, travertine decking, and inspiring partial Bay views of Sarasota Bay and the Ca’ d’Zan. The showpiece chef’s kitchen sets the standard for luxury with custom Devittori cabinetry, level 5 leathered granite, and a massive 11’x5’ island crafted from a single granite slab. Outfitted with premium Sub-Zero and Wolf appliances, including a 60” range with double ovens, six burners, dual griddles, a pot filler, Sub-Zero wine fridge, refrigerator drawers, and designer hood. Enjoy deeded private beach access, or join the nearby Longboat Key Club for world-class golf, tennis, and dining—all minutes from St. Armands Circle and Downtown Sarasota. Live the Longboat Key waterfront lifestyle—where boating, beach, and luxury converge in one extraordinary home.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
560 HARBOR POINT RD, LONGBOAT KEY, FL 34228
$9,700,000230 Days on yellowkey MLS ID: A4671218
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5245 Built: 2011Monthly Fee: $802 Tax: $46,237 (2025)Community: Bay IslesSpa: NoSingle Family
Taxes:$46,237
Remarks: Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost 200 feet of pristine waterfront, with breathtaking views of the downtown Sarasota skyline and a protected deep-water yacht slip. Deeded access to a private Gulf of Mexico beach club enhances the ultimate coastal lifestyle. Inside, the home features an exceptional floor plan with four luxurious bedroom suites and numerous entertainment spaces, including a formal living room, dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. Expansive waterfront terraces, a redesigned viewing porch, and his-and-her offices add to the home's functional elegance. Every detail has been executed to perfection, from the impeccable millwork to the finest finishes throughout. With magical views from every room, this estate embodies class, comfort, and privacy in one of Sarasota's most coveted locations. Experience refined waterfront living at its finest.
Listing Agent: Jonathan Fox, Pa (941-544-6649)
3548 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,895,000138 Days on yellowkey MLS ID: A4681540
REDUCED by $100,000 (3.3%) on 05/08/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3470 Built: 2000Monthly Fee: $833 Tax: $24,368 (2025)Community: Queens HarbourSpa: NoSingle Family
Taxes:$24,368
Remarks: Located within the gated Queens Harbour enclave in Bay Isles, this direct bayfront residence offers a well-designed courtyard-style floor plan with water views, flexible living spaces, and a private dock—set on a quiet cul-de-sac in one of Longboat Key’s most established communities. Spanning approximately 3,470 square feet of living space across two levels, the home features four bedrooms, four full baths, and one half bath, with a layout that prioritizes privacy and functionality. The first floor hosts three en-suite guest bedrooms, a dedicated office, and the main living areas, while the entire second floor is reserved for the primary suite, creating a true owner’s retreat. The main level welcomes you with an open living and dining arrangement highlighted by cathedral ceilings, tile flooring, and walls of sliding glass doors that open to the bayfront patio. This seamless indoor-outdoor connection frames tranquil water views, ideal for relaxing or entertaining. The formal dining space also enjoys bayfront exposure and flows naturally into the kitchen. The kitchen is thoughtfully positioned for daily living and gatherings, offering solid wood cabinetry, stone countertops, a center island, breakfast bar seating, pantry storage, and a full suite of stainless-steel appliances. Adjacent family and living spaces enhance the home’s livability while maintaining clear sightlines to the water. Two of the first-floor guest bedrooms include en-suite baths, while a third guest suite—a private cabana across the pool courtyard—offers flexibility for visiting family or multi-generational living. The office is also located on the first level, providing the ideal amount of separation. Upstairs, the primary suite occupies the entire second floor, offering privacy and elevated views. This retreat features a spacious bedroom, walk-in closet, and a well-appointed en-suite bath with dual sinks, soaking tub, separate shower, and private water closet. Outdoor amenities include a private pool courtyard, open dock with direct bay frontage, providing access for boating and paddle sports. A new tile roof was installed in 2023, and the property includes a two-car garage. Queens Harbour residents enjoy a maintenance-free lifestyle with 24-hour guard-gated security, community heated pool and spa. Ownership also includes deeded access to the private Bay Isles Beach Club, offering Gulf-front pavilions, grilling areas, and pristine beaches just minutes away. Perfectly positioned behind the gates of Bay Isles, this residence is close to Harbourside Golf & Marina, the Longboat Key Club, and island dining. St. Armands Circle, Lido Beach, and downtown Sarasota are all within easy reach, providing access to shopping, waterfront restaurants, cultural venues, and year-round events. A well-located bayfront opportunity offering space, privacy, and a flexible floor plan in one of Longboat Key’s most desirable communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
610 HIBISCUS WAY, LONGBOAT KEY, FL 34228
$2,650,00056 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)
524 HALYARD LN, LONGBOAT KEY, FL 34228
$5,495,000299 Days on yellowkey MLS ID: A4663499
0 Days Off yellowkey (back on 5/16/2026)
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: Under contract-accepting backup offers. 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)
690 FOX ST, LONGBOAT KEY, FL 34228
$725,000133 Days on yellowkey MLS ID: A4682225
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1967 Tax: $10,397 (2025)Community: Longbeach On Longboat KeySingle Family
Taxes:$10,397
Remarks: Buy the beach house, now is your opportunity! New unbelievable price on this fully renovated and turn-key furnished Village of Longboat Key Home. Take Advantage Today. Brand new Roof, New Hurricane glass throughout, Full interior renovation with new furnishings, Block home on a Beautiful private lot with outdoor living space and room for a Pool, steps away from white sand and turquoise water, rent-ability with the seller averages $55,000 a year in gross rental income while still enjoying personal use. Buy this property at an unbelievable price, rent it when you're not using it, and enjoy it for decades to come. Coastal Elegance Meets Island Ease in Longboat Key's Coveted Village. Discover a sanctuary of sophistication at the exclusive North Tip of Longboat Key. Located in the heart of historic Long Beach Village, this is more than a home; it's the ultimate island lifestyle, delivered. Just a short, serene stroll separates you from the pristine beach and the island's best waterside dining. This property has been meticulously and fully remodeled, representing a rare "move-in ready" opportunity where every detail has been elevated. From top to bottom, inside and out, virtually nothing has been untouched. A Home Designed for Seamless Living: Open Concept: Step into an airy, open-plan great room, anchored by a brand-new kitchen - perfect for hosting intimate gatherings or unwinding after a day on the water. Chef's Delight: The remodeled kitchen is a masterpiece featuring stunning marble countertops, custom cabinetry, all-new luxury appliances (including a mini wine refrigerator), and a chic island/bar. High-End Finishes: Enjoy the cohesive flow of new luxury vinyl plank flooring throughout every room, complemented by fresh, designer-selected interior paint. Peace of Mind: Recently installed, all new windows and sliding glass doors are Miami-Dade impact resistant, offering superior protection and efficiency. Also a brand new architectural three-tab shingle roof was just installed. Your Private Island Retreat: Spa-Inspired Baths: Both the master and second bathrooms have been fully renovated with premium stone shower flooring, elegant new tiles, and updated fixtures. Outdoor Oasis: Off the master suite, a new impact-resistant glass door opens to a spacious, private backyard. The highlight is the expansive, screened-in porch that wraps around the back of the house, overlooking a charming outdoor fire pit and grilling area. Beach Ready: An exterior shower and dedicated storage for your gear make rinsing off after a day at the beach effortless. The Village Lifestyle: To know The Village is to fall in love with its relaxed, yet refined rhythm. This community places everything you desire at your fingertips: secluded walking trails, Bay access, community docks, and the island's best beach access. The Village is one of the few places on Longboat Key where the golf cart isn't just legal, it's the preferred, fun, and convenient way to live. Come and see it today.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
1005 BOGEY LN, LONGBOAT KEY, FL 34228
$3,300,000148 Days on yellowkey MLS ID: A4680006
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3624 Built: 2017Monthly Fee: $21 Tax: $19,847 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$19,847
Remarks: Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.
Listing Agent: Michael Nink, Pa (941-914-2805)
562 RANGER LN, LONGBOAT KEY, FL 34228
$3,499,900187 Days on yellowkey MLS ID: A4675541
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3149 Built: 1995Monthly Fee: $20 Tax: $27,065 (2024)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$27,065
Remarks: One or more photo(s) has been virtually staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern rear exposure overlooking the canal, with a north-facing street frontage, providing balanced natural light throughout the day. The home underwent a comprehensive renovation in 2018, including a tile roof, paver driveway, two Trane A/C units, tankless water heater, updated sprinkler system, railings, pool equipment, and a Pebble Tec refinished pool positioned to maximize the southern exposure. The interior features an open great-room layout with 16-foot ceilings, porcelain tile flooring throughout, plantation shutters, LED lighting, and a spacious kitchen with Starmark solid-wood soft-close cabinetry, Cambria quartz countertops, and stainless-steel appliances. An 8-foot arched iron front door introduces abundant natural light and an open, functional floor plan. The current configuration includes an upper-level primary suite with solid oak flooring, walk-in closets, and a well-appointed bath, while the first level offers three large bedrooms, including an office with custom built-ins, and two full baths with handcrafted cabinetry, quartz countertops, and glass-enclosed showers. The flexible layout provides the opportunity to create a first-floor primary suite to suit individual lifestyle needs. Boating amenities include a new seawall, a 70-foot private Trex dock with 50-amp shore power, and a recently serviced 10,000-pound boat lift. Outdoor living is enhanced by a covered lanai and a two-level travertine deck ideal for entertaining and enjoying the canal setting. Residents enjoy access to a private deeded beach on the Gulf of Mexico and proximity to Longboat Key Club golf, dining, and shopping at St. Armands Circle, with downtown Sarasota’s cultural arts and dining scene just minutes away. Schedule a private showing to experience this waterfront home, its flexible living options, and direct access to Sarasota Bay
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Cheri Mazan Castro (941-400-3777)
578 COMPANION WAY, LONGBOAT KEY, FL 34228
$900,000133 Days on yellowkey MLS ID: A4682186
REDUCED by $99,000 (9.9%) on 05/07/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoSingle Family
Taxes:$11,672
Remarks: Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
3598 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,795,000163 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.
519 ROUNTREE DR, LONGBOAT KEY, FL 34228
$6,488,00070 Days on yellowkey MLS ID: A4690210
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3554 Built: 2025Monthly Fee: $250 Tax: $9,330 (2024)Community: Longboat Key EstatesSpa: YesSingle Family
Taxes:$9,330
Remarks: BUILT TO LAST. 519 Rountree is new construction built entirely of concrete block (CBS) across every level—unlike many barrier island homes that transition to wood-frame construction above the flood elevation. The residence has already experienced recent hurricanes without damage. NEW CONSTRUCTION. 519 ROUNTREE is a privately positioned coastal residence offering over 6,400 square feet of indoor and outdoor living, including approximately 5,200 square feet under roof and a 1,100 square foot elevator-accessible rooftop terrace, located within Longboat Key Estates. GULF LIVING EXPERIENCE. At 519 Rountree, days begin with morning air carrying the salt-kissed character of the Gulf and conclude with glowing sunsets that define the Florida coastline. This is not simply proximity to the beach — it is immersion in it. Positioned just moments from the sand, the home offers balcony and rooftop experiences designed for sunset entertaining, open-air dining, and the effortless rhythm of Gulf living from morning through evening. WATERFRONT LIVING. A waterside deck is currently in process, transforming the canal setting into a true extension of the home’s outdoor living experience, subject to permitting. Flexibility remains for a variety of dock and lift configurations, tailored to buyer preference. DESIGN AND EXECUTION. The newly constructed residence has withstood three recent hurricanes without damage, a testament to its quality, elevation, and thoughtful execution. Each level is purposeful in both design and function, delivering a vertical lifestyle that feels intuitive, private, and refined. FURNISHINGS. For buyers seeking the residence exactly as photographed, the complete furnishings and curated design package may be acquired separately. FINAL NOTE. 519 Rountree delivers the atmosphere buyers seek when they say they want Gulf living — quietly, privately, and without excess.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Colby Lengel (941-779-6227)
5970 EMERALD HARBOR DR, LONGBOAT KEY, FL 34228
$2,795,000128 Days on yellowkey MLS ID: A4681905
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3098 Built: 1977Monthly Fee: $63 Tax: $12,915 (2024)Community: Emerald Harbor Unit 1 RevSpa: NoSingle Family
Taxes:$12,915
Remarks: Set at the peaceful end of a wide, deep canal on the north end of Longboat Key, this waterfront residence in Emerald Harbor offers a rare combination of space, privacy and effortless boating access. With long views straight down the canal and quick entry to Sarasota Bay, the setting feels calm, open and ideally positioned for life on the water. A circular paver brick drive framed by meticulously maintained landscaping leads to the front entrance, where a barrel tile roof and timeless exterior details create a welcoming first impression. Inside, 3,098+/- sq. ft. of thoughtfully planned living space unfolds in soft neutral tones, complemented by abundant natural light, large tile flooring, crown molding and expansive windows throughout the main living areas. The living room is designed for seamless indoor-outdoor living, featuring a full wall of pocket sliders that open completely to a covered sitting area accented by a pecky cypress ceiling. From here, the view extends across the pool, private dock and calm canal beyond, creating a natural backdrop for both entertaining and everyday enjoyment. The kitchen anchors the home with ease and functionality, offering a center island with breakfast bar, wood cabinetry, stone countertops, stainless steel appliances, tile backsplash and pendant lighting. Its placement allows the home to flow comfortably for gatherings or quiet evenings alike. The floor plan offers exceptional flexibility, with two generously sized suites. The main primary suite features a tray ceiling, a large custom walk-in closet and a beautifully updated bath with dual vanities, glass-enclosed shower and convenient access to the outdoor living area. A second suite includes its own custom walk-in closet and en suite bath, making it ideal for guests or extended family. Two additional bedrooms and a study overlooking the water complete the layout, along with three and a half total baths. Outdoors, the setting feels private yet expansive, with a sparkling pool and a private dock equipped with a boat lift. The canal offers excellent boating water with no-bridge access to the Intracoastal Waterway, Sarasota Bay and the Gulf. Emerald Harbor is a bayside enclave of just 82 homes, known for its broad lagoon-style canals and deeded private beach access located one block away.
Listing Agent: Bruce Myer (941-376-5311)
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