Location: Longboat Key
Do Not Show Listings
705 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$2,795,00016 Days on yellowkey MLS ID: A4696488
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3083 Built: 2011 Tax: $38,157 (2025)Community: Shipmans AddSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$38,157
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Tucked away on the coveted north end of Longboat Key, this custom-designed coastal contemporary residence offers a rare blend of modern architecture, boating access, and waterfront living. Designed by architect Mark Sultana of DSDG, the home was completed in 2011. Positioned along a protected saltwater canal with private dockage and just moments from the Gulf's sandy shoreline, this island retreat captures tranquil water views, tropical surroundings, and spectacular sunsets from multiple levels. Spanning nearly 3,100 square feet, the four-bedroom layout is designed for effortless indoor-outdoor living. The main level serves as the heart of the home, where soaring 18-foot whitewashed cypress ceilings crown the open great room. A contemporary gas fireplace with gray glass tile anchors the living area, while walls of impact-rated glass fill the residence with natural light and frame views of the canal and lush mangroves beyond. The open-concept design seamlessly connects the living room, dining area, and gourmet kitchen, creating an ideal environment for both entertaining and everyday enjoyment. The chef's kitchen is appointed with custom solid-wood cabinetry by Campbell Designs, quartz countertops, glass tile backsplash, breakfast bar, oversized pantry, water filtration, and premium appliances. Thoughtful details such as Lutron lighting system, built-in audio throughout the interior and exterior, impact-rated doors and windows, soft-close drawers, metal barrel roof, propane-fueled pool heater and outdoor grill, oversized two-car garage with workshop, abundant storage, and dedicated kayak storage enhance both function and style. An open staircase crafted from powder-coated aluminum with blonde maple treads creates an architectural focal point while connecting the living spaces. The second level is devoted to private accommodations, including two guest bedrooms sharing a beautifully appointed bath, with one currently configured as a den. The upper floor is highlighted by the primary suite featuring dual walk-in closets, a private waterfront terrace, and spa-inspired bath with freestanding soaking tub, marble-topped dual vanity, oversized glass shower, and separate water closet. Adding exceptional flexibility, a detached cabana suite overlooks the pool deck and serves as a private guest retreat. Complete with a full bath, walk-in closet, morning kitchen, and separate entrance, this space functions perfectly as a fourth bedroom, guest quarters, home office, or artist's studio. Outdoor living is equally impressive. White terrazzo terraces on each floor overlook the 36-foot lap pool and spa with waterfall feature, creating a private tropical setting enhanced extensive landscape lighting, mature exotic foliage, and lush zoysia grass. The private IPE wood dock includes an 8,000-pound lift, kayak launch, water and electric service, and underwater lighting for boating enthusiasts. Located on one of Longboat Key's most desirable stretches, residents enjoy deeded access to the island's pristine Gulf beach just across the street, waterfront dining, marinas, and scenic biking paths. The Longboat Key Club's golf and tennis facilities are nearby, while St. Armands Circle offers boutique shopping and acclaimed restaurants just minutes away. Downtown Sarasota's cultural attractions are easily accessible, creating an exceptional coastal lifestyle that blends privacy, recreation, and convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
548 GUNWALE LN, LONGBOAT KEY, FL 34228
$2,100,000144 Days on yellowkey MLS ID: A4680965
REDUCED by $100,000 (4.5%) on 06/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 1967Monthly Fee: $17 Tax: $9,801 (2025)Community: Country Club Shores Sec 1Spa: YesSingle Family
Taxes:$9,801
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Country Club Shores - Completely renovated 3-bedroom, 2-bath canal-front home just three houses from the Bay. Updates include a new flat tile roof (2025), Carrier A/C and A.O. Smith water heater (2024), Pebble Tec pool and paver deck (2024), and newer seawall, dock, and 16,000 lb. boat lift (2.5 years). Enjoy Bay views from the 18 foot x 16 foot Trex dock with lighting and water, plus a 3 foot x 36 foot Trex dock with power and water. Interior features NuCORE waterproof flooring, plantation shutters, Silestone quartz countertops, and new Bosch and GE stainless appliances. The primary suite includes a walk-in closet with built-ins, dual sinks, whirlpool tub, and large shower. Split floor plan with guest bedrooms featuring walk-in closets; one includes a built-in office area. Move-in ready and ideally located for boaters seeking the best of Longboat Key waterfront living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: John August (941-320-9795)
635 MARBURY LN, LONGBOAT KEY, FL 34228
$1,945,000136 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
Tax Year: 2024
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)
1600 HARBOR SOUND DR, LONGBOAT KEY, FL 34228
$11,900,00057 Days on yellowkey MLS ID: A4692027
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5689 Built: 2026Monthly Fee: $792 Tax: $24,527 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$24,527
High School: None
Middle School: None
Remarks: Pre-Construction. To be built. Positioned directly across from the iconic St. Regis Longboat Key Resort, this exceptional waterfront residence offers immediate access to world-class amenities, pristine Gulf beaches, fine dining, and championship golf. Located within the exclusive double-gated Harbor Section of Bay Isles on Longboat Key, 1600 Harbor Sound Drive represents a rare convergence of scale, location, and boating capability, crafted for those seeking a refined Gulf Coast lifestyle at the highest level. Set on an expansive 18,043-square-foot corner homesite, the property features an impressive 135 feet of deep-water canal frontage, with the ability to accommodate multiple lifts (up to three) and a substantial vessel. This level of frontage and flexibility is increasingly rare, even among premier waterfront estates. Spanning 5,689 square feet under air, the residence is thoughtfully designed to balance grand-scale entertaining with comfortable everyday living. The home includes 5 bedrooms, a bonus room or office, 5.5 bathrooms, and a 4-car garage. Soaring ceilings and expansive glass openings create a bright, open environment with seamless indoor-outdoor transitions, complemented by refined, designer-level finishes and a private elevator servicing all levels. The chef’s kitchen is executed with top-tier appliances, clean architectural lines, and a level of detail rarely seen in spec construction. A full-scale butler’s pantry, complete with its own stove, provides exceptional functionality and allows for seamless entertaining while keeping the main kitchen pristine. The primary suite is designed as a true retreat, featuring separate his-and-her bathrooms and a fully integrated wellness experience, including a sauna and steam room, bringing a spa-level environment into daily living. Every element has been carefully curated to deliver comfort, functionality, and a sense of understated luxury throughout. Outdoor living is equally compelling, with a resort-style pool and spa, along with a fully equipped outdoor kitchen, covered dining, and lounge areas. These spaces are perfectly positioned to capture the tranquility of the waterfront setting while embracing Florida’s year-round coastal climate. Opportunities of this caliber, combining substantial frontage, strong boating capability, a wellness-driven design, and a premier Harbor Section address are increasingly limited. 1600 Harbor Sound Drive presents a compelling offering for the discerning buyer seeking a newly built waterfront estate in one of Sarasota’s most prestigious enclaves.
Listing Agent: Rinat Sikdar (941-993-9292)
550 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$1,295,000122 Days on yellowkey MLS ID: A4683082
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1758 Built: 1977 Tax: $6,151 (2025)Community: Sleepy Lagoon ParkSingle Family
Taxes:$6,151
Remarks: One or more photo(s) has been virtually staged. Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dean Hinterstoisser (941-726-0314)
500 HARBOR COVE CIR, LONGBOAT KEY, FL 34228
$12,250,0004 Days on yellowkey MLS ID: A4697649
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5120 Built: 2026 Tax: $20,619 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$20,619
High School: Riverview High
Remarks: Under Construction. Now nearing completion and expected to be delivered in approximately 60 days. Positioned within the exclusive Harbor Section of Bay Isles on Longboat Key, 500 Harbor Cove Circle is a newly constructed waterfront estate offering a rare combination of exceptional boating access, modern architecture, resort-inspired living, and one of the Gulf Coast’s most coveted addresses. Located behind the double gates of Bay Isles and directly across from The St. Regis Longboat Key Resort, residents enjoy immediate proximity to world-class hospitality, fine dining, marina services, championship golf, and tennis, while ownership includes access to the Bay Isles Beach Club. Encompassing 5,120 square feet under air and 8,564 square feet total, the residence features 5 bedrooms, 5 full baths, 1 half bath, a private office, elevator access to all levels, and a 4-car garage. A fully integrated smart home automation system provides seamless control of lighting, climate, security, audio, window treatments, pool and spa functions, and key home systems throughout the property. The arrival experience unfolds through a lagoon-inspired reflecting pool, floating stairway, and lush tropical landscaping, creating a dramatic resort-style arrival. Architectural lighting, natural stone, warm wood accents, and expansive walls of glass establish a sophisticated coastal aesthetic throughout the residence. Inside, expansive living spaces are enhanced by Venetian plaster, custom millwork, large-format stone surfaces, and carefully curated architectural details. One of the home’s defining architectural statements is a dramatic 20+ foot monolithic travertine feature wall wrapping an entire corner of the residence, creating a striking design element rarely found in residential construction. The chef’s kitchen is anchored by an oversized Calacatta marble waterfall island, premium custom cabinetry, integrated appliances, and generous entertaining space. Designed for seamless indoor-outdoor living, the residence opens to expansive covered terraces, a resort-style pool and spa, and a fully equipped outdoor kitchen featuring a grill, pizza oven, refrigeration, and multiple gathering spaces. Wellness-focused amenities include a private fitness area, sauna, cold plunge, and dedicated spaces for relaxation and recovery, creating a private wellness retreat. For boating enthusiasts, the property offers approximately 100 feet of protected waterfront frontage with direct access to Sarasota Bay and the Gulf of Mexico in less than two minutes. The dock is designed to accommodate a substantial yacht while still providing room for multiple additional lifts for a tender, fishing boat, personal watercraft, and other recreational vessels—an increasingly rare offering among Florida’s premier waterfront estates. One of the Gulf Coast’s rare opportunities to enjoy new construction, large-yacht capability, and resort-inspired living within the exclusive Harbor Section of Bay Isles.
7143 LA LENAIRE DR, LONGBOAT KEY, FL 34228
$5,995,00030 Days on yellowkey MLS ID: A4694196
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2721 Built: 2010Monthly Fee: $317 Tax: $17,255 (2025)Community: Jew Fish KeySingle Family
Taxes:$17,255
Elementary School: None
Remarks: Private island living on Jewfish Key, one of eight homes, accessible by boat only. This rare offering presents a lifestyle few will ever experience: a secluded island sanctuary surrounded by the turquoise waters of Longboat Pass and the Gulf Coast’s natural beauty. An address like this comes up for sale about once a generation. 7143 La Lenaire is on the market for the first time in more than two decades. The home is a custom built, over 2,700 square feet of living space designed to embrace panoramic water views and effortless indoor-outdoor living, four bedrooms and four baths, finished in 2011 on a 1.24-acre titled lot with roughly 300 feet of water frontage. From the island you are minutes by water to Longboat Key, St Armands Circle, and Anna Maria Island. Every room captures breathtaking western-facing vistas, creating a constant backdrop of sparkling water, coastal breezes, and unforgettable sunsets. The main living areas open onto covered outdoor space and frame the sunset over the intercoastal waters, and the evening light fills the rooms. It was built to handle a quiet weekend or a full house of guests. The private deep-water dock provides immediate boating access to Sarasota Bay, the Intracoastal Waterway, Longboat Key Pass, and the Gulf of Mexico, making this a true boater’s paradise. Jewfish Key is a hidden gem spanning approximately 38 acres, offering a level of privacy and tranquility rarely found along Florida’s Gulf Coast. Surrounded by pristine shoreline, sandbars, native wildlife, and crystal-clear waters, the island delivers an unmatched blend of exclusivity and natural beauty while still being conveniently located near Longboat Key, Anna Maria Island, and Sarasota’s world-class dining, shopping, and entertainment. Whether used as a private family compound, luxury waterfront getaway, or one-of-a-kind investment opportunity, 7143 La Lenaire Drive represents a truly irreplaceable island lifestyle. Turn Key - Furnished.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000227 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
Remarks: A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$4,999,00031 Days on yellowkey MLS ID: A4694394
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3842 Built: 2000Monthly Fee: $833 Tax: $29,486 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$29,486
Remarks: Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living spaces, and direct boating access, all within one of Longboat Key’s most sought-after neighborhoods. From the moment you arrive, the home’s meticulous maintenance and thoughtful renovations are immediately apparent. A roof just two years old, hurricane shutters on all windows and doors, and multiple updated mechanical systems provide exceptional value and confidence for years to come. Inside, the residence has been extensively renovated in 2026 with stunning new engineered wood flooring flowing throughout the home, creating a warm and welcoming coastal aesthetic. The spacious floor plan offers five generously sized bedrooms, ideal for accommodating family and guests while maintaining privacy and flexibility for today’s lifestyle needs. The heart of the home is the beautifully refreshed kitchen, complete with brand-new KitchenAid appliances installed in 2026, blending modern functionality with timeless design. Adjacent living and dining areas are filled with natural light and seamlessly connect to the outdoor entertaining spaces, creating an inviting atmosphere perfect for both everyday living and hosting gatherings. Every bathroom in the home was completely renovated in 2026 with stylish finishes and contemporary details that elevate the home’s overall elegance. Extensive system upgrades include three HVAC systems replaced in 2022, 2023, and 2026, along with a new hot water heater installed in 2026, ensuring maximum efficiency and comfort throughout the property. Outdoor living is equally impressive and designed to embrace the Florida waterfront lifestyle. The pool area underwent a significant transformation in 2025 with new pool decking, a resurfaced pool finish, updated waterline tile, and a new gas pool heater, creating a true private resort setting. In 2026, the addition of a fully equipped outdoor kitchen elevated the entertaining experience even further, offering the perfect backdrop for waterfront dining and sunset gatherings. Boating enthusiasts will appreciate the new 10,000-pound boat lift installed in 2025 along with a beautifully updated dock and deck, providing quick and convenient access to Sarasota Bay and the Gulf waters beyond. Combining luxury updates, exceptional outdoor amenities, and a premier location within the coveted Bay Isles community, with private beach club access, this extraordinary Longboat Key residence presents a rare opportunity to enjoy refined waterfront living with every major improvement already completed.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
624 SAINT JUDES DR, LONGBOAT KEY, FL 34228
$700,000218 Days on yellowkey MLS ID: A4672840
REDUCED by $49,900 (6.7%) on 06/11/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1387 Built: 1957 Tax: $8,692 (2025)Community: Longboat KeySingle Family
Taxes:$8,692
Remarks: You’ve watched, you’ve waited, and now the moment to act is here. The seller is ready to pivot their investment strategy, and they’ve authorized a limited-time price adjustment on this property. Effective immediately, the price has been reduced to $700,000—but this offer is locked in only until next Friday. If this was the home you were waiting for, the hesitation ends today. Let’s get you into your new property before this window closes. The stunning Cali-Modern residence has a new, more attractive price! Presenting an amazing opportunity for this stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. Presenting a stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. This sophisticated, move-in ready home offers an abundance of good vibes and professional quality, available now on the highly sought-after North End of exclusive Longboat Key. Sleek, chic, and absolutely move-in ready, this property is an instant atmosphere setter. From the moment you step inside, you'll feel the coastal modern bliss. Enjoy the clean, modern lines, vaulted ceilings, and stunning stone tile floors, all bathed in gorgeous southern sun light. The upgraded kitchen and bathrooms sparkle with new features, complemented by new appliances. This home has been lovingly and extensively renovated, offering quality and style that goes well beyond the expected. You will find thoughtful design and premium features in every corner. Step outside to your own private backyard oasis, the perfect spot to sip a sunset cocktail. Fully fenced and private this oasis sets up perfectly for the future pool. And talk about location! You are literally steps from both Gulf and Bay access. This home boasts unbeatable walkability to island favorites like Harry's Deli and The Continental Kitchen, Euphymya Haye and the Hayloft, Lo-Key Island Grille, Cedars East Tennis and Fitness Resort and many others. The best-kept secret? A private back gate leads you directly into the 32 acres of Joan Durante Park, offering pure, natural Florida coastal hammock. This park is a true gem filled with nature walking trails, fishing piers, playground for the kids and multiple Bay access points (perfect for the kayak launch) No fuss, no stress. With a standing seam metal roof, Hardi board siding, newer double-pane windows, New interior, new appliances and offered fully furnished, this charmer is ready for your island life to begin immediately. Don't wait, come feel the charm for yourself!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
602 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$1,399,00010 Days on yellowkey MLS ID: A4697037
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2107 Built: 1961Monthly Fee: $50 Tax: $12,286 (2025)Community: Buttonwood HarborSingle Family
Taxes:$12,286
High School: Sarasota High
Remarks: Expect luxury living and a world of conveniences within the serene enclave of Buttonwood Harbour on Longboat Key, where care and impeccable style converge in this 3BR/3BA tropical oasis. As you approach, the vast circular paver drive, embraced by lush, professionally maintained landscape, sets the stage for what awaits beyond the architecturally pleasing covered front entryway. Step inside to discover the attention to detail that defines this updated home, as gorgeous new tile floors throughout grace and harmonize with neutral tones and exquisite touches, including stately plantation shutters adorning every window. The flowing floor plan effortlessly guides you to the expansive pool area, blending indoor elegance with outdoor convenience. The beautifully remodeled kitchen is both stylish and functional, seamlessly connected to the living room, and featuring a large breakfast Island, tile backsplash, a wine refrigerator, and Bosch appliances. Relax in the cozy Florida room, which offers a tranquil retreat with walls of sliders that blur the boundaries between indoor and outdoor living. Outside, the sparkling heated pool beckons, surrounded by ample space on the lanai for entertaining or simply basking in the tropical ambiance. The expansive primary suite is a sanctuary of comfort, with slider access to the pool area, new tile flooring, and a remodeled primary bath boasting dual vanities and a glass-enclosed walk-in shower adorned with stunning tilework. Equally inviting, the two guest accommodations offer spacious comfort, with elegantly remodeled bathrooms. Set in a prized mid-key location, Buttonwood Harbour offers residents a short walk to the beach and a community Harbor with boat slips available to lease.
Listing Agent: Michelle Musto (941-809-3714)
541 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$830,00058 Days on yellowkey MLS ID: A4691592
0 Days Off yellowkey (back on 5/4/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1704 Built: 1976 Tax: $5,286 (2025)Community: Sleepy Lagoon ParkSpa: NoSingle Family
Taxes:$5,286
Remarks: Under contract-accepting backup offers. An incredible opportunity for a canal front 3 bedroom home on a nicely elevated lot. This home had NO WATER INTRUSION from the storms! It is a diamond in the rough just waiting for your vision. Whether you remodel it and use it as a monthly waterfront rental or make plans to turn it your vacation or waterfront island home, the lot itself is worth the price! Walk to the neighborhood beach, or jump on your boat out back on your lift and cruise the intracoastal.....this is a great chance to start your island living dreams.
793 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$1,749,00015 Days on yellowkey MLS ID: A4695252
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2688 Built: 2007 Tax: $16,753 (2025)Community: Longboat KeySpa: YesSingle Family
Taxes:$16,753
Remarks: Longboat Key Waterfront Home combining Canal frontage & Deeded Beach Access. Key West-style home featuring 4-beds, 3.5-baths offering 2,688 SF on a .32-acre lot with 154 feet of canal waterfrontage. Elevated, engineered for storms, and built in 2007built in 2007 with concrete block construction, Hardie board siding, hurricane impact windows and doors, and a standing seam metal roof. A classic Key West-inspired design with an expansive wraparound porch, Barbados-style railings, and mature tropical landscaping creates an immediate sense of arrival. The paved driveway leads to a 2-car garage with an air-conditioned storage closet. Step through the beveled glass entry door with sidelights and into a grand living room with soaring 22-foot ceilings, a wood-burning fireplace, and a sweeping staircase that anchors the space. Plantation shutters throughout the home enhance the island vibe. The main living level is open and connected. The kitchen is outfitted with a center island, dual sinks, stainless steel appliances, stone countertops, dual pantries, and separate dining areas. A comfortable den is ideal for reading or watching the game, while a main-level office and bedroom with a full bath serve perfectly as a guest suite or in-law accommodation. Upstairs, the owner's suite is a genuine island escape. Two walk-in closets, two sets of glass French doors opening to an expansive private covered balcony. Spa-inspired bathroom with limestone floors, dual sinks, a soaking tub, and a separate shower. Two additional guest bedrooms share a full bathroom and a dedicated laundry area, each with its own balcony offering peaceful views. Throughout the home, wide-plank hardwood and travertine tile flooring, 8-foot doors, window seating, French doors, custom lighting, and custom bathroom tile showcase craftsmanship and quality. Outside, a large heated pool and spa sit within a beautifully landscaped two-story screened enclosure, with a pavered walkway leading to the dock at the water's edge — ready for your boat, kayak, or simply an evening watching the dolphins and manatees pass by. A screened lanai overlooks the canal, the perfect spot for a morning coffee or an evening cocktail. You are just four homes from Sarasota Bay with direct boating access in minutes and no bridges to open water. Deeded beach access to the Gulf of Mexico is directly across the street, where nightly sunsets are a daily ritual and the powdery sand of the Gulf shoreline is your backyard extension. Joan Durante Park is a short distance away. The neighborhood allows monthly rentals with an optional HOA — seasonal rental potential OK. The dining and lifestyle amenities: Harry's Continental Kitchen, Euphemia Haye and Loft, Shore Restaurant, and Drydock Waterfront Grill w/waterfront dining. The Longboat Key Club's two championship golf courses mean you never have to leave the island. The St. Regis Longboat Key, famous St. Armands Circle, and the energy of Sarasota. Sold furnished.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Sunni Hammermeister (239-822-3332)
530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$4,295,000248 Days on yellowkey MLS ID: A4669195
REDUCED by $200,000 (4.4%) on 06/16/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$12,064
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.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
3040 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$1,899,00052 Days on yellowkey MLS ID: A4692587
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3009 Built: 1995 Tax: $8,653 (2025)Community: Triton CoveSpa: YesSingle Family
Taxes:$8,653
Remarks: Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St. Armands Circle. An elevated entry leads to the main living level, where expansive glass defines the open-concept design, connecting the living room, kitchen and dining areas. Positioned within a five-residence enclave, this property offers convenient access to Sarasota dining, shopping and waterfront recreation while supporting a low-maintenance ownership experience. This tri-level single-family home features four bedrooms and 2.5 baths, complemented by a two-car garage with dual 8-foot doors and extensive storage. The ground level includes multiple flexible-use rooms ideal for fitness, storage or organization of beach equipment, kayaks, bicycles and boating gear. A dumbwaiter provides direct access from the garage to the kitchen. Interior features include engineered wood flooring in main living areas and new carpet in bedrooms. The kitchen is designed with wood cabinetry, granite countertops, deep storage drawers, an appliance garage, a rollout pantry wall and stainless steel appliances, including a GE wall oven/microwave combo, an induction cooktop and an LG refrigerator. Additional features include a wet bar with cabinetry and a mirrored wall, an electric fireplace and plantation shutters. The primary suite offers a private setting with dual vanities, a soaking tub, a separate shower, two walk-in closets and a Juliette balcony with partial gulf views. The third level includes a bonus room suitable for media, an office or a private retreat. Outdoor living includes a natural gas-heated pool and spa, an outdoor shower and a private fenced setting. Pool systems including a new motor, filters and heater, and the interior of the pool has been refinished. Recent improvements include a 2024 shingle roof with warranty, zoned HVAC systems installed in 2018 and 2020, and a 2025 water heater. The home includes a monitored alarm system. Triton Cove offers a maintained environment with low monthly HOA fees of $500, including landscape maintenance of common areas, pest control, pool service and exterior lighting. Leasing is permitted up to four times annually with a one-month minimum. Located near Longboat Key Bayfront Park and Longboat Dog Park, residents may enjoy pickleball, tennis, playgrounds and picnic areas. Nearby conveniences include grocery, pharmacy, boat rentals and storage options along Longboat Key, as well as being within reach of Sarasota amenities. Optional membership to the Longboat Key Club provides access to golf, tennis, beach and social amenities, enhancing the gulf-front lifestyle experience on Florida's west coast. Don’t miss out on your private tour of this special coastal home featuring four bedrooms, 3000-plus square feet of air-conditioned living space, a two-car garage, a 30-foot pool and a hot tub on Longboat Key with beach access with low taxes for under $2 million; this is an extraordinary value!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Frank Lambert (941-920-1500)
549 HALYARD LN, LONGBOAT KEY, FL 34228
$2,195,0004 Days on yellowkey MLS ID: A4696535
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1594 Built: 1965Monthly Fee: $23 Tax: $20,602 (2025)Community: Country Club ShoresSingle Family
Taxes:$20,602
Remarks: This is the one * PERFECTLY POSITIONED ON A QUIET CUL DE SAC STREET AT THE PREFERRED SOUTH END OF LONGBOAT KEY * Located on the QUIET END OF THE CANAL with OPEN WATER JUST BEYOND YOUR DOCK and the PRIVATE BEACH ACCESS ONLY MINUTES AWAY * A quick 3 minute cruise to Sarasota Bay & the ICW & The GULF * This coveted Country Club Shores IV home has been LOVINGLY RENOVATED with a NEW Kitchen & modern amenities while retaining its classic charm * NEW KITCHEN CABINETS * NATURAL GAS STOVE * GE CAFE APPLIANCES * NEW Solid Core Doors * FULL HURRICANE PROTECTION * NEW TILE Flooring throughout * 2 Car Garage has a NEW Mini Split A/C * Primary Suite with a Spa-style Bath featuring a LARGE Walk-in Shower * BEAUTIFUL VIEWS OF YOUR POOL & PRIVATE CANAL * This THOUGHTFULLY CURATED HOME is an open floor plan * The additional Bedrooms are well-appointed and located in a way that allows for guest privacy * Impact Sliding Glass Doors surround the Outdoor Area * All of this wraps your Caged Pool with Paver Decking and a Paver Walkway to your 2021 NEW SEAWALL & COMPOSITE DOCK with a 10,000lb Boat Lift & 2 Additional NEW Jetski Lifts PLUS a 2-step down Kayak Dock Launch with Power & Water * THIS IS A BOATER'S DREAM * The PERFECT HOME & OUTDOOR OASIS to entertain family & friends or just simply relaxing in your slice of paradise * PRIDE OF OWNERSHIP SHOWS IN THIS IMMACULATE HOME * Furniture is available * Just bring your suitcase * Country Club Shores is a well established waterfront neighborhood offering DEEDED BEACH ACCESS with a convenient south end location close to ST ARMAND'S CIRCLE, The new ST REGIS, and even downtown Sarasota * Join the Longboat Key Club offering 45 holes of championship golf & world class tennis * Your family will love this home * One look & you'll fall in love! *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Brown (941-330-7774)
626 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$4,495,00015 Days on yellowkey MLS ID: A4696767
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2026Monthly Fee: $50 Tax: $4,789 (2025)Community: Longboat Shores RevSpa: YesSingle Family
Taxes:$4,789
Remarks: Experience the pinnacle of coastal living in this exceptional new construction waterfront residence, ideally situated in the heart of Longboat Key. Perfectly positioned across from the community marina with direct boating access to the Gulf of Mexico, this move-in-ready home offers an extraordinary blend of modern elegance, superior craftsmanship, and the relaxed sophistication of island life. Spanning 4,106 square feet, this thoughtfully designed residence features 4 spacious bedrooms, a private office/den, and 4 luxurious bathrooms, creating an ideal setting for both everyday living and entertaining. Finished floor elevation above base flood elevation, the home provides added peace of mind while maximizing its commanding presence. Designed to embrace Florida’s indoor-outdoor lifestyle, expansive sliding glass doors seamlessly connect the interior living spaces to two generous covered lanais, overlooking a resort-style heated pool and spa. Whether hosting sunset gatherings or enjoying a quiet morning overlooking the water, every space has been crafted to capture the beauty and serenity of waterfront living. Inside, sophisticated finishes and attention to detail abound. Wide-plank engineered hardwood flooring flows throughout the home, complemented by designer quartz countertops, custom cabinetry, and an open-concept floor plan filled with natural light. The chef-inspired kitchen serves as the centerpiece of the home, featuring an oversized island, premium finishes, and a spacious walk-in pantry. The convenience of dual laundry rooms further enhances the home's thoughtful design. For boating enthusiasts, the property features a concrete seawall and marina access, offering quick and convenient access to Sarasota Bay and the Gulf waters beyond—making it easy to enjoy world-class fishing, waterfront dining, and unforgettable days on the water. A boat slip is currently leased by the owner. Tucked away on a quiet street, yet just moments from Longboat Key’s pristine white-sand beaches, championship golf courses, marinas, boutique shopping, and renowned dining destinations, this residence delivers the perfect balance of privacy and accessibility. Offering the rare combination of new construction, waterfront location, elevated construction, luxury finishes, and Gulf boating access, 626 Buttonwood Drive represents an exceptional opportunity to own a premier Longboat Key waterfront retreat in one of Florida’s most coveted coastal communities. Luxury. Boating. Beach Life. Welcome Home.
569 BAYVIEW DR, LONGBOAT KEY, FL 34228
$4,695,000323 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
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.
597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$3,890,000494 Days on yellowkey MLS ID: A4640902
Bed: 5 Bath: 6.0 Gar: 5 Liv Area Sq Ft: 4176 Built: 2025 Tax: $7,998 (2024)Community: Buttonwood HarborSpa: YesSingle Family
Taxes:$7,998
Remarks: New Construction.... GULF AND BAY VIEWS! THREE OUTDOOR PATIOS! Discover an extraordinary coastal contemporary masterpiece by Floridian Crafted Homes, perfectly positioned on Longboat Key with breathtaking Gulf and Bay views. This 13 FEET ELEVATED, hurricane-fortified residence offers 5 bedrooms, 5 full bathrooms, and 2 partial bathrooms across 4,176 square feet of luxurious living space. Home has elevator shaft blocked in and ready to receive elevator mechanics. Designed for both elegance and functionality, this home features three expansive outdoor living spaces, including two private balconies and a stunning rooftop deck, perfect for capturing the serene Gulf sunsets. The open-concept great room flows effortlessly into the gourmet kitchen, creating an entertainer’s dream, while the second-floor club room offers a private retreat for relaxation. Outdoors, a private pool and spa provide a tranquil escape, while the 5+ car garage ensures ample storage for vehicles and beach essentials. Located just steps from the beach and steps to the upcoming retail and dining destination (Est. Fall 2025), this home also offers access to a community marina with available boat slips, making it ideal for boating enthusiasts. Experience the pinnacle of modern coastal luxury in this exceptional Longboat Key residence—where timeless design, breathtaking views, and an unparalleled location create the ultimate island retreat.
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,00035 Days on yellowkey MLS ID: A4694532
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4154 Built: 1994Monthly Fee: $833 Tax: $22,710 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$22,710
Remarks: Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Miriam Pearson (941-726-4687)
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