Location: Longboat Key , 34228
Do Not Show Listings
2800 HARBOURSIDE DR #F-06, LONGBOAT KEY, FL 34228
$339,000138 Days on yellowkey MLS ID: A4684822
0 Days Off yellowkey (back on 7/13/2026)
Bed: Bath: 0.0 Built: 1985Monthly Fee: $573 Tax: $3,032 (2025)Community: Bay IslesDock-Rackominium
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,032
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Slip F-06 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 70 X 26, and a usable beam of 23 feet and a 32 FT long finger pier. This location provides close proximity to parking with a view of the west side of the marina and golf courses. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 65 feet. Beam; on the vessel type and measure. Membership in the Longboat Key Club is required.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
1945 GULF OF MEXICO DR #M2-402, LONGBOAT KEY, FL 34228
$515,00018 Days on yellowkey MLS ID: TB8525404
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 933 Built: 1978Monthly Fee: $1,333 Tax: $5,390 (2025)Community: Seaplace VCondo
Taxes:$5,390
Elementary School: None
High School: None
Middle School: None
Remarks: Seaplace Condominiums, half mile Gulf of Mexico beachfront property with chaise lounges & umbrellas provided on private beach portion. Elegant turnkey-furnished unit with hurricane impact doors & windows. Next to clubhouse pool, gym, sauna & community kitchen. Two properties from St. Regis Resort restaurants & beach bar.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
4234 GULF OF MEXICO DR #M1, LONGBOAT KEY, FL 34228
$649,00031 Days on yellowkey MLS ID: A4696419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $2,383 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$2,383
Remarks: COMMUNITY BOAT SLIP AVAILABLE! It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. At this writing, community has two 30 ft boat slips available at $600 per year. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: John Thorson, Pa (941-914-1366)
617 ROUNTREE DR, LONGBOAT KEY, FL 34228
$2,350,00069 Days on yellowkey MLS ID: A4692822
REDUCED by $145,000 (5.8%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1972 Built: 1998Monthly Fee: $250 Tax: $7,892 (2025)Community: Longboat Key EstatesSpa: NoSingle Family
Taxes:$7,892
Remarks: Discover the perfect canvas for your coastal vision in the prestigious Longboat Key Estates. This premier waterfront opportunity offers 100 feet of direct canal frontage in one of the island’s most desirable enclaves. Positioned on a quiet interior street, this property sits in an area undergoing significant luxury transformation, providing an ideal foundation for a custom residence with superior investment potential. The deep-water canal offers bridge-free access minutes to Sarasota Bay, while the property features a 2022 seawall and a 16,000-pound boat lift (2022). Residents of this deed-restricted community enjoy private deeded beach access complete with a private neighborhood Tiki. Ideally located next to Bayfront Park—offering tennis, pickleball, kayaking, trails, and a fishing pier—you are also minutes from fine dining, St. Armands Circle, downtown Sarasota, and Sarasota International Airport. This is truly a unique opportunity to secure your place in a fabulous neighborhood where modern, high-end living is setting the new standard!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Judi Taulbee (941-544-6227)
3598 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,795,000189 Days on yellowkey MLS ID: A4677923
1 Days Off yellowkey (back on 4/18/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3417 Built: 1996Monthly Fee: $833 Tax: $15,229 (2025)Community: Queens HarbourSpa: NoSingle Family
Taxes:$15,229
Remarks: Situated within the gated Queens Harbour enclave of Bay Isles, this thoughtfully updated four-bedroom courtyard residence offers a refined blend of privacy, comfort, and waterfront living on Longboat Key. Designed around a lush central courtyard, the home creates an effortless indoor-outdoor flow anchored by a resurfaced swimming pool and new paver deck—an inviting retreat for everyday living or entertaining. A private cabana suite with its own entrance provides flexibility for guests or extended stays, enhancing the home’s functionality while maintaining separation from the main living areas. Entry begins through custom mahogany and glass double doors, opening to a reimagined open-concept interior with soaring 14-foot ceilings, wide-plank wood flooring, and carefully curated architectural detail throughout. The great room is centered around a travertine-encased electric fireplace and framed by walls of windows and glass sliders that capture tranquil lake views and abundant natural light. This space flows seamlessly into the formal dining area, highlighted by a statement chandelier and tongue-and-groove tray ceiling, and continues into the chef’s kitchen—designed as the heart of the home. The kitchen features a dramatic 14-foot quartz-topped island, custom designer cabinetry by Sarasota Architectural Woodworking, and newer Thermador appliances, including a five-burner gas cooktop, dual built-in ovens, pull-out pantry cabinetry, and a 48-inch stainless sink. Adjacent informal dining and family spaces include aquarium-style glass windows and an oversized wet bar with a full-size wine cooler capable of storing over 100 bottles. The primary suite, located on the main level, offers a peaceful lakefront setting with French-door access to the patio, custom built-in storage, and a walk-in closet. The spa-inspired bath was recently updated with dual quartz-topped walnut vanities, soaking tub, glass-and-stone shower, and private water closet. Also on the first floor are a versatile study overlooking the courtyard and a bonus room with an attached full bath that can serve as an additional bedroom or media space. The second level is dedicated to a private en-suite guest bedroom. Queens Harbour residents enjoy access to a heated Olympic-size pool and spa, along with deeded entry to the private Bay Isles Beach Club. Beyond the gates, Longboat Key’s lifestyle amenities are just minutes away, including the Longboat Key Club’s golf and tennis facilities, marinas, dining, and everyday conveniences. St. Armands Circle and downtown Sarasota’s cultural attractions—shopping, galleries, theaters, and waterfront dining—are easily accessible, completing the appeal of this well-positioned coastal residence.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
7143 LA LENAIRE DR, LONGBOAT KEY, FL 34228
$5,995,00054 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
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)
3010 GRAND BAY BLVD #432, LONGBOAT KEY, FL 34228
$1,245,000147 Days on yellowkey MLS ID: A4683353
2 Days Off yellowkey (back on 7/13/2026)
REDUCED by $154,000 (11.0%) on 05/21/2026
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2143 Built: 1999Monthly Fee: $175 Tax: $14,342 (2025)Community: Grand Bay 4Condo
Taxes:$14,342
Remarks: Under contract-accepting backup offers. Step into the foyer from your private elevator and through chic double doors into this fully furnished Grand Bay masterpiece where drama meets elegance. Floor-to-ceiling glass sliders reveal a breathtaking panorama of the downtown city skyline, John Ringling Bridge, Harbourside golf course, and Sarasota Bay. The open floor plan seamlessly connects the living and dining areas to a versatile den—perfect as a media room or a third bedroom. Equipped with premium KitchenAid appliances, a Subzero and a central island, the kitchen includes an eating space for casual mornings. Wake up to panoramic bay views in the primary suite featuring private access to a massive wraparound terrace. The spa-like primary bath offers a garden soaking tub, dual vanities, a glass-enclosed shower and walk-in closet. The ensuite guest room ensures privacy and comfort, complete with its own stunning views of the water and greens and terrace access. Located behind the prestigious Longboat Key Club gates, residents enjoy double-gated security, Har-Tru tennis courts, a fitness center, a recently renovated Clubhouse and two heated pools. Grand Bay residents have private access to the Bay Isles Beach Club, all while being minutes away from the world-class shopping of St. Armands Circle and the cultural hub of downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
793 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$1,749,00039 Days on yellowkey MLS ID: A4695252
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2900 Built: 2007 Tax: $16,753 (2025)Community: Longboat KeySpa: YesSingle Family
Taxes:$16,753
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
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.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Sunni Hammermeister (239-822-3332)
5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$7,495,000214 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
Tax Year: 2024
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.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
630 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$8,925,000420 Days on yellowkey MLS ID: A4653251
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 4591 Built: 2022 Tax: $58,070 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$58,070
Remarks: This stunning Bayfront estate delivers over 480 feet of pristine Bayfront waterfront on a prime point property. True Longboat Key gold. Special features of this home include five bedrooms, five full bathrooms, hardwood floors, sky-high ceilings plus walls of glass. The home opens to multiple covered terraces built for soaking in endless Bay views and the best of Florida living at its finest. The open-concept layout blends indoor comfort with outdoor style, perfect for hosting or unwinding in total privacy. The kitchen is sleek and spacious with high end Wolf package and Sub Zero ready for gourmet meals or casual bites with a view. The adjoining family room also features a large stone fireplace. The primary suite is a retreat all its own with private terrace access, spa-style bath and water views that never quit. Outside, the lifestyle really takes off. A large Bayfront resort-style pool with a hot tub anchors the backyard, surrounded by multiple fire pits perfect for evening gatherings under the stars. Need space for guests? A separate guest house is available to design to your personal touch, offers total privacy and comfort, ideal for hosting family or friends without sacrificing your own space. This estate isn’t just a home it’s a waterfront playground built for bold living. There's kayak storage and room for multiple docks and all your water toys. The new seawall built in 2010 adds peace of mind. There is a four car garage. This North Longboat property is a must see for anyone seeking a luxurious lifestyle combined with natural beauty. With its modern amenities, prime location, and stunning views, it stands out as a dream home. Don’t miss the opportunity to make this exquisite residence your own. This north Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.
4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228
$330,000185 Days on yellowkey MLS ID: A4678473
1 Days Off yellowkey (back on 7/13/2026)
REDUCED by $20,000 (5.7%) on 06/18/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,196 Tax: $4,937 (2025)Community: Longboat HarbourCondo
Taxes:$4,937
Remarks: Under contract-accepting backup offers. Unlock the Door to Your Dream Beach and Boating Lifestyle! Step into a world of unparalleled charm with this move-in ready, fully furnished gem on Longboat Key. This isn’t just a home; it’s a transformative lifestyle choice for those craving adventure, relaxation, and vibrant social connections. Picture yourself waking up to breathtaking bay views every morning from your stylish condo, featuring elegant granite countertops, state-of-the-art appliances, and a spa-like shower that redefines luxury. Your perfect beach days await with exclusive private beach access, complete with a dedicated beach house that offers showers and restrooms for your convenience. For boating enthusiasts, the Longboat Key Yacht Club provides convenient boat slips and kayaks, giving you immediate access to the pristine waters of the bay. Stay energized and engaged with an array of top-tier amenities, including tennis courts, shuffleboard, a rejuvenating sauna, and a fully equipped gym. Join a dynamic social scene filled with workshops, a cozy library, an inspiring art studio, and clay classes, plus the warm camaraderie of the Book Buddies club that fosters connections. With four inviting swimming pools, a grand banquet hall for gatherings, a fun game room for entertainment, and convenient private beach parking, every day feels like a luxurious getaway. This is more than just a condo; it’s a lifestyle experience you truly deserve. Don’t let this extraordinary Longboat Key oasis pass you by! Schedule your showing today and discover if it’s your perfect match!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Rademacher (612-965-6188)
4440 EXETER DR #301, LONGBOAT KEY, FL 34228
$535,000137 Days on yellowkey MLS ID: A4684917
REDUCED by $5,000 (0.9%) on 07/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $8,101 (2024)Community: Longboat HarbourCondo
Taxes:$8,101
Remarks: Motivated Seller, make an offer. Welcome to this beautifully updated top floor corner furnished residence with Gulf and Bay views that is move in ready. Coming furnished with an open kitchen floor plan and an enclosed lanai overlooking the pool and Sarasota Bay. Large plank ceramic tiles throughout and ceiling fans in every room, hurricane impact glass windows in the kitchen and living area and a washer/dryer has been added. All tv's within the residence stay. The Longboat Harbour community is located mid-Longboat Key with amenities to enjoy including a large clubhouse where many activities occur, with a catering kitchen and dance floor, art studio, billiard and card rooms, and a fully equipped fitness center. In addition, the community has four heated swimming pools, putting green, tennis and pickleball courts, kayak storage, boat slips available for a minimal annual fee for up to a 34’ boat, mini golf, a scenic waterfront promenade along the harbor and canal, and access to a private gated Beach Club on the Gulf side with bathrooms, showers and beach items. The building has just completed a new roof installed. There is additional storage withing the building for each residence as well as a storage closet on the enclosed lanai.
Listing Agent: Michael Moulton (941-928-3559)
5260 GULF OF MEXICO DR #413, LONGBOAT KEY, FL 34228
$550,00018 Days on yellowkey MLS ID: A4698906
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1155 Built: 1974 Tax: $2,618 (2025)Community: The Banyan Bay ClubCondo
Taxes:$2,618
Remarks: Move-in-ready condition, ground-floor bayside condominium with Sarasota Bay views and deeded private Gulf beach access in the sought-after Banyan Bay Beach Club! Discover effortless coastal living in this beautifully updated 2-bedroom, 2-bath residence offering 1,155 square feet on the bayside of Longboat Key. Thoughtfully renovated throughout, this inviting home features new luxury vinyl plank flooring, new kitchen appliances, updated bathrooms with new vanities, and a bright, open floor plan designed for comfortable island living. Enjoy Sarasota Bay views from the living room, primary bedroom, and private rear patio. Step directly from your patio onto the beautifully landscaped lawn, where you can enjoy your morning coffee, watch boats and dolphins pass by, observe abundant coastal wildlife, and welcome beautiful Florida sunrises. The convenient ground-floor location offers effortless access and seamlessly blends indoor and outdoor living. Residents of this pet-friendly community enjoy the best of both worlds with deeded private Gulf beach access and outstanding amenities, including a heated pool, clubhouse, pickleball, tennis, fishing pier, kayak storage and launch, and assigned parking. Whether you enjoy boating, kayaking, fishing, shelling, or relaxing on the beach, this community offers the quintessential Longboat Key lifestyle. Ideally located near championship golf, waterfront dining, marinas, boutique shopping, St. Armand's Circle, and downtown Sarasota, this exceptional residence is perfect as a primary home, seasonal retreat, or investment opportunity. Don't miss this rare opportunity to own an updated, move-in-ready, bayside condominium with Sarasota Bay views, deeded private Gulf beach access, and the relaxed elegance of island living. EASY TO SHOW. SUPRA ON storeroom door across from front door.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Bobbie Banan (941-356-2659)
602 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$1,399,00034 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)
311 FIREHOUSE CT, LONGBOAT KEY, FL 34228
$2,399,000300 Days on yellowkey MLS ID: A4665445
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2352 Built: 2005Monthly Fee: $467 Tax: $29,195 (2025)Community: Conrad BeachSingle Family
Taxes:$29,195
Remarks: NEWLY PRESENTED & FULLY FURNISHED. Some homes invite you to exhale the moment you arrive. This is one of them. Nestled within the award-winning Conrad Beach community on Longboat Key — ideally positioned west of Gulf of Mexico Drive — this elevated coastal residence is offered fully furnished as a true Gulf Coast retreat. Set within an intimate enclave of architect-designed homes, it delivers a rare combination of privacy, tranquility, and timeless coastal character that grows harder to find with each passing season. Designed for effortless island living, the home pairs classic coastal architecture with resort-inspired interiors and a relaxed elegance that feels both welcoming and refined. Mornings begin with coffee on the porch as tropical landscaping sways in the Gulf breeze. Evenings unfold on the upper west-facing deck as golden light dissolves into the water. Thoughtfully designed landscape lighting transforms the grounds after dark, making every night feel like an occasion. Inside, freshly refreshed interiors are curated for comfort, connection, and easy entertaining. The gourmet kitchen anchors the home around an oversized quartz island where guests naturally gather. Open-concept living spaces flow seamlessly outdoors, while a spacious lanai extends the entertaining footprint — with flexibility for future enclosure if desired. The main-level primary suite offers a peaceful escape with its own private balcony overlooking lush tropical surroundings. Upstairs, guest bedrooms and a loft-style family room accommodate visitors with ease — equally suited to seasonal stays, remote work, or multi-generational living. A two-car garage supports a true lock-and-leave lifestyle, while Firehouse Court's no street parking policy preserves the quiet, residential character of the neighborhood. Community amenities include a resort-style pool, entertaining areas, bath facilities, and observation spaces — all maintained through remarkably low HOA fees that cover lawn care, landscaping, irrigation, and common area upkeep. For peace of mind, the home is equipped with high-impact windows and doors, a whole-house fire sprinkler system, and a full-house generator. For buyers seeking relief from crowded beaches and hurried routines, the contrast is immediate — life here is open, unhurried, and ready to enjoy from day one. Just over the bridge, Anna Maria Island offers waterfront dining, boutique shopping, and the kind of authentic Old Florida charm that keeps everyone coming back. Minutes from the pristine beaches of Longboat Key's coveted north end, this is more than a home. It's where lasting memories are made, priorities reset, and a life you've been waiting to live finally begins.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
4350 CHATHAM DR #Unit E-208, LONGBOAT KEY, FL 34228
$640,000234 Days on yellowkey MLS ID: A4672221
REDUCED by $35,000 (5.2%) on 06/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1969 Tax: $6,535 (2025)Community: Longboat HarbourCondo
Taxes:$6,535
Remarks: One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $35,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Building E #208 | Corner End Unit • Bay & Harbour Views. CLOSEST BUILDING TO A SHORT WALK ACCROSS THE STREET WITH A PRIVATE DEEDED GULF BEACH ACCESS WITH PAVILION, RESTROOMS AND SHOWERS TOTALLY REMODELED FROM FLOOR TO CEILING second-floor corner residence in the highly sought-after Longboat Harbour Community. This light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour. This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available. From the two bedrooms, you step out to the exceptionally Large Lanai with floor to ceiling sliding glass doors. A SHOWCASE KITCHEN WITH TWO SUNLIT WINDOWS AND WATER VIEWS Elegant, functional, and beautifully appointed: • Frigidaire Professional stainless steel appliances • Gleaming quartz countertops • 9-inch deep sink • Pull-out cabinet shelving • Pantry closet • Designer tile backsplash • Large Eat-In Kitchen with water views & sunsets • Instant hot-water. LUXURIOUS PRIMARY SUITE An elevated retreat professionally designed for comfort and relaxation • Private ensuite bath • Custom California Closet walk-in wardrobe • Built-in desk feature • Remote-controlled luxury solar shades. RESORT-INSPIRED AMENITIES Longboat Harbour offers a lifestyle unmatched on the Gulf Coast: • Designated covered parking spot conveniently located • Personal storage space on the third floor • Private deeded Gulf beach access with pavilion, restrooms & shower • Four sparkling pools • Fitness center & sauna • Tennis & pickleball courts • Billiards room, library & meeting rooms • Picnic areas with grills • Putting green • Fishing pier • Affordable resident-only boat dockage • KAYAK LAUNCH and KAYAK WHICH SELLER WILL BE GIFTING TO THE BUYER. Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key. PROPERTY ENHANCEMENTS & UPDATES: Thoughtfully improved for comfort, reliability, and peace of mind: • NO HURRICANE DAMAGE OR FLOODING • Bosch Washer & Dryer • Newer AC: 12/5/21 • Newer Hot Water Heater: 3/3/17 • New roofs throughout the community • Electrical and plumbing systems updated. A BEAUTIFULLY RENOVATED INTERIOR THAT CREATES THE ULTIMATE COASTAL LIFESTYLE/ THE MONTHLY HOA FEE INCLUDES HAZARD, HURRICANE AND FLOOD INSURANCE/ RESERVES HAVE BEEN FULLY FUNDED
Listing Agent: Billie Chipain (941-587-8556)
4725 GULF OF MEXICO DR #314, LONGBOAT KEY, FL 34228
$724,900226 Days on yellowkey MLS ID: A4673798
REDUCED by $25,000 (3.3%) on 06/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1104 Built: 1974 Tax: $10,125 (2024)Community: Sand CayCondo
Taxes:$10,125
Remarks: Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A well-established vacation rental with a strong income history, this property is an ideal opportunity for both personal enjoyment and investment. Nestled within an intimate beachfront community offering 340 feet of pristine Gulf frontage, Sand Cay provides an exceptional resort-style experience. Residents and guests enjoy first-class amenities including tennis courts, shuffleboard, a heated pool, basketball area, barbecue stations, a full-time on-site manager, and a convenient in-house rental program. Perfectly located, the resort is just minutes from the boutique shops and fine dining of St. Armands Circle and the vibrant arts and cultural attractions of downtown Sarasota. Light and bright, this third-floor garden-view condo is ideally situated between the pool and the beach. The inviting floor plan features two bedrooms, two bathrooms, a spacious living and dining area, an updated and fully equipped kitchen, a cozy den/office nook, and a private balcony with an awning—ideal for morning coffee or unwinding after a day by the Gulf. Your slice of Longboat Key paradise awaits. Schedule your showing today.
Listing Agent: Michael Albano, Pa (941-993-9571)
71 TWIN SHORES BLVD, LONGBOAT KEY, FL 34228
$395,00010 Days on yellowkey MLS ID: A4699581
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 758 Built: 2026Monthly Fee: $280 Tax: $1,627 (2025)Community: Twin Shores Mobile HomeSpa: NoManufactured Home
Taxes:$1,627
Remarks: Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated over 6 feet, 2-bedroom, 2 bath, open floorplan home. HURRY and you can help design your new home and deck. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickleball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! RUN, don't walk, paradise awaits! *** Lot #96 is also available and under construction. ***
Listing is courtesy of: EVENTIDE REALTY LLC (941-799-9190)
Listing Agent: Kyle Adams (941-799-9190)
2425 GULF OF MEXICO DR #14B, LONGBOAT KEY, FL 34228
$1,699,000413 Days on yellowkey MLS ID: A4654664
INCREASED by $9,000 (0.5%) on 07/10/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $18,495 (2024)Community: Sea Gate ClubSpa: YesCondo
Taxes:$18,495
Remarks: BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!
Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)
Listing Agent: Andrey Markov (941-363-1043)
1241 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$3,200,00042 Days on yellowkey MLS ID: A4695733
2 Days Off yellowkey (back on 7/10/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2965 Built: 1996 Tax: $29,387 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$29,387
Remarks: Under contract-accepting backup offers. Water Clubs most exquisitely renovated residence just became available for the first time! Meticulously reimagined from the studs up, this “Beach Beauty” immerses you in the essence of the Gulf below, every detail from the Azure toned palette to the warm honey finishes evoke a serene coastal escape with walls of windows frame the sweeping vistas from Bay to Beach while expansive terraces flow seamlessly between indoor and outdoor living - perfect for elegant entertaining or peaceful solitude. This modified “Dover” renovated floor plan Is located in the highly desirable end “8” stack which has amazing full gulf and bay views, the advantage of the private wrap around terraces elevate you above the lush tropical canopy to be soothed by remarkable natural light and uninterrupted vistas. Rich wide plank wood flooring sets a warm sophisticated tone throughout this impeccably designed residence. Only the finest finishes were selected, with designer fixtures, custom details and elegant appointments. Bespoke lighting creates a captivating ambience while custom remote shades and luxurious sheer drapery blend harmoniously with the curated furnishings. Offered beautifully “turnkey furnished” every detail is already in place allowing you to begin enjoying this extraordinary coastal retreat from the moment you arrive! Flowing seamlessly from the great room the stunning open concept kitchen is designed for both gourmet cooking and gracious entertaining. At its heart, a chef inspired island invites friends and family to join in creating culinary creations, Wine enthusiasts will appreciate the custom Euro wine cave perfectly positioned to keep your favorite vintages at hand for impromptu gatherings or elegant dinners. The exceptional kitchen is appointed with premium Thermador built-in appliances, induction cooktop, creamy quartz countertops, custom cabinetry with convenient pantry pullouts, and thoughtful storage throughout. Serving as a true sanctuary, the primary suite exudes the ambience of an exclusive spa retreat with a beautifully appointed vestibule separating the walk-in closet from the private luxurious bathroom. The primary bath with walk-in shower flows into the elegant sophisticated “boudoir” appointed with bespoke fixtures, and luxurious bedding and linens. Step out to the private terrace where the sounds of the Gulf will lull you to sleep. The 2nd Guest ensuite has an amazing Bay view terrace to enjoy the twinkling lights across the Bay at night. The generous walk-in closet is stocked with exquisite bedding, and towels to make your guests feel pampered. The full bath includes a walk-in shower, quartz vanity, and elevated lighting. The 3rd bed/den is a great escape for the kids or a private yoga studio - it segues smartly with the 3rd bathroom right down the hall for convenience, decorated with the same style and quality of décor and finishes. The Water Club is known for its full 24 hour concierge service, resort style living, offering children’s pool, 3 spas, 4 har-tru tennis courts, a Mediterranean spa clubhouse with fitness center, steam and sauna, library, many social spaces and Water Club is “pet-friendly”. Every corner of this amazing property has been reimagined with the finest materials and thoughtful design - It’s truly an artistic creation you must see to appreciate. Call now for a private showing.
Listing Agent: Kathy Callahan (941-900-8088)
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