Location: Longboat Key
Do Not Show Listings
2600 HARBOURSIDE DR #Q-08, LONGBOAT KEY, FL 34228
$225,000305 Days on yellowkey MLS ID: A4664910
Bed: Bath: 0.0 Built: 1985Monthly Fee: $322 Tax: $2,506 (2025)Community: Bay IslesDock-Rackominium
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,506
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: A fantastic view of the city skyline from the 48 x 21 foot slip at Longboat Key Club Moorings! Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call to discuss!
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
2800 HARBOURSIDE DR #F-06, LONGBOAT KEY, FL 34228
$339,000132 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
Taxes:$3,032
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.
1945 GULF OF MEXICO DR #M2-402, LONGBOAT KEY, FL 34228
$515,00012 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
$649,00025 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
$2,350,00063 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
$2,795,000183 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
$5,995,00048 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
$1,245,000141 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
$1,749,00033 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)
530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$4,295,000266 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
Tax Year: 2024
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)
626 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$4,495,00033 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.
4325 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$1,100,00060 Days on yellowkey MLS ID: A4693621
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1336 Built: 1975 Tax: $4,084 (2025)Community: Tiffany PlazaSpa: NoCondo
Taxes:$4,084
Remarks: Experience coastal living in this two-bedroom, two-bath direct Gulf-front residence ideally on the main floor of a desirable mid-rise community on Longboat Key. Freshly painted and thoughtfully enhanced with quartz countertops in both the kitchen and laundry room, along with recently updated washer and dryer appliances, the residence also features crown molding, updated trim and plantation shutters throughout, as well as Gulf-side hurricane shutters. The covered Gulf-side lanai provides the perfect setting to relax and enjoy the coastal surroundings year-round. The primary bedroom offers a very large walk-in closet. This residence includes a designated covered parking space along with private exterior storage. Residents enjoy an impressive array of amenities, including a clubhouse with a sauna, a heated Gulf-front pool, an interlocking stone patio and barbecue, a covered area and direct beach access. Ideally in a sought-after mid-key location, the property is close to St. Armands Circle, with its renowned boutiques, dining and shopping, while downtown Sarasota is just over the bridge, offering arts, culture, dining and entertainment. Heading north, enjoy convenient access to Anna Maria Island, while heading south, you will find the many amenities of Longboat Key, including Publix, CVS, places of worship, banks, parks, town hall, Bayfront Park, public tennis courts, boat launches and more.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
2301 GULF OF MEXICO DR #44N, LONGBOAT KEY, FL 34228
$625,0005 Days on yellowkey MLS ID: A4699335
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $2,713 (2025)Community: Islander Club Of LongboatCondo
Taxes:$2,713
High School: Pine View School
Middle School: Pine View School
Remarks: Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$7,495,000208 Days on yellowkey MLS ID: A4673495
REDUCED by $305,000 (3.9%) on 05/08/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4630 Built: 2018Monthly Fee: $572 Tax: $30,971 (2024)Community: Bonaire At Longboat KeySpa: YesSingle Family
Taxes:$30,971
Remarks: Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.
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
$8,925,000414 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
$330,000179 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
$535,000131 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)
569 BAYVIEW DR, LONGBOAT KEY, FL 34228
$4,695,000341 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.
5260 GULF OF MEXICO DR #413, LONGBOAT KEY, FL 34228
$550,00012 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)
2350 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$950,0004 Days on yellowkey MLS ID: A4699679
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2451 Built: 1987Monthly Fee: $1,617 Tax: $9,783 (2025)Community: Harbour Oaks 2Villa
Taxes:$9,783
Remarks: Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Jason Wood (941-993-6565)
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