Location: Longboat Key
Do Not Show Listings
617 WESTON POINTE CT, LONGBOAT KEY, FL 34228
$3,100,00012 Days on yellowkey MLS ID: A4697745
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4395 Built: 1994Monthly Fee: $708 Tax: $27,075 (2025)Community: Weston PointeSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$27,075
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Welcome to **617 Weston Pointe Court**, where timeless elegance meets the Florida waterfront lifestyle. Nestled within one of Longboat Key's most desirable gated golf communities, this exceptional **four-bedroom, five-bathroom** residence offers an extraordinary blend of luxury, privacy, and direct boating access to the Gulf. From the moment you step inside, you'll be captivated by the expansive open floor plan, soaring ceilings, and breathtaking views overlooking the tranquil canal. Designed for both everyday living and effortless entertaining, the spacious great room flows seamlessly into the gourmet kitchen and dining areas, creating a bright and inviting atmosphere throughout the home. The thoughtfully designed floor plan features a luxurious primary suite and two additional bedrooms on the main level, while the upstairs loft provides a versatile living space accompanied by an additional guest bedroom, offering comfort and privacy for family and visitors alike. At the heart of the home lies an incredible private courtyard oasis. The sparkling pool creates a resort-style setting between the main residence and a detached cabana complete with its own kitchenette and full bathroom—an ideal space for overnight guests, a private office, fitness studio, or poolside entertaining. For boating enthusiasts, this property truly stands apart. The **privately owned boat slip conveys with the home**, offering exceptional value and convenience. Positioned as the **last slip on the left**, it provides one of the easiest locations in the marina for entering and exiting with your boat, making every trip on the water effortless. The slip is equipped with a **boat lift**, and from your dock, it's approximately **15 minutes through the scenic canal to the open waters of the Gulf**, allowing you to spend less time navigating and more time enjoying life on the water. Whether you're hosting elegant gatherings around the courtyard pool, enjoying peaceful waterfront sunsets, or setting out for a day of boating, this remarkable Longboat Key residence offers the perfect combination of luxury, comfort, and coastal living. Don't miss this rare opportunity to own an exceptional waterfront home complete with a transferable private boat slip in one of Longboat Key's most sought-after communities. Schedule your private showing today and experience Florida waterfront living at its finest.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jason Kranz, Pa (352-446-6001)
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$975,000118 Days on yellowkey MLS ID: A4686721
REDUCED by $120,000 (11.0%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3040 GRAND BAY BLVD #213, LONGBOAT KEY, FL 34228
$1,460,000180 Days on yellowkey MLS ID: A4678941
REDUCED by $90,000 (5.8%) on 07/09/2026
Bed: 2 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1996 Tax: $8,474 (2025)Community: Grand Bay 2Spa: YesCondo
Taxes:$8,474
Remarks: Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
6001 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$9,995,000284 Days on yellowkey MLS ID: A4667111
5 Days Off yellowkey (back on 7/9/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6959 Built: 2013 Tax: $105,194 (2024)Community: Longboat KeySpa: YesSingle Family
Taxes:$105,194
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly placed on nearly an acre of pristine Gulf-front property along the shoreline on Longboat Key. With direct Gulf frontage, this architectural masterpiece offers more than 6,900 square feet of refined interiors and panoramic views that stretch endlessly across the Gulf of Mexico. Designed for both privacy and grand-scale entertaining, the residence balances timeless craftsmanship with recent enhancements including a 2025 primary bath remodel, newer French doors, and resort-style pool and spa with natural gas heating and fire pit. From the moment you arrive through the circular drive, the home’s elegant façade, manicured landscaping, and elevated design make a commanding first impression. Inside, expansive living areas are defined by travertine and hardwood flooring, soaring coffered ceilings, crown molding, and walls of glass framing breathtaking views. The open floor plan flows effortlessly from the formal living and dining rooms to the family room and gourmet kitchen, designed for effortless entertaining. The chef’s kitchen showcases custom wood cabinetry, granite counters, a large island, high-end appliances, double ovens, and a breakfast nook overlooking the Gulf. The main-floor primary suite offers a serene retreat with direct beach views, its own private terrace, dual walk-in closets, and a spa-like new bath featuring dual vanities, stone counters, and a freestanding soaking tub. A private elevator connects all levels, including a versatile second-story loft, media room, and four additional bedrooms (some en-suite) providing ample comfort for family and guests. The outdoor living space defines Florida luxury—complete with an expansive travertine deck, heated pool and spa, summer kitchen, and multiple covered terraces designed for dining and relaxation. Enjoy vibrant sunsets over the Gulf from nearly every vantage point. The property also features new hurricane-rated French doors, a whole-house generator with raised platform, and a three-car side-entry garage with guest parking. Located on the prestigious north end of Longboat Key, this gated estate offers the perfect balance of seclusion and accessibility. Stroll along miles of private beach or take a short drive to the Longboat Key Club, offering championship golf, tennis, and fine dining. Just minutes away, St. Armands Circle and downtown Sarasota offer a vibrant mix of boutique shopping, art galleries, and acclaimed restaurants. With world-class marinas, cultural landmarks, and pristine beaches within reach, this exceptional residence captures the very best of Sarasota’s luxury coastal lifestyle. Offering an unparalleled combination of design, craftsmanship, and Gulf-front serenity, 6001 Gulf of Mexico Drive stands as a statement of timeless coastal elegance—where every sunset feels like home.
Listing Agent: Roger Pettingell (941-387-1840)
3301 BAYOU RD, LONGBOAT KEY, FL 34228
$1,250,00073 Days on yellowkey MLS ID: A4692818
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2827 Built: 1993Monthly Fee: $104 Tax: $12,771 (2025)Community: Bay IslesSingle Family
Taxes:$12,771
Remarks: Located within the gated and highly desirable community of Bay Isles on Longboat Key, this 4 bedroom, 3 bathroom pool home encompasses 2827 square feet of living space. The residence features a functional and spacious floor plan, including a well-appointed bedroom layout, an open kitchen and family room combo, and a formal living and dining room combo. This property is priced competitively, offering an exceptional opportunity for a buyer or investor to come in and renovate the home with their own personal style and modern finishes. The outdoor living area features a private pool, providing a quiet retreat within a stunning waterfront community. Bay Isles residents enjoy a premier island lifestyle with access to a private beach area and cabana, while separate memberships are available for those interested in world-class golf or the local marina. The location is ideal for enjoying the best of the Florida Gulf Coast, situated in close proximity to local restaurants, boutique shopping, and the famous St. Armand's Circle. Whether you are looking for a primary residence or a seasonal getaway, this home serves as the perfect canvas to create a custom masterpiece in one of Longboat Key's most sought-after enclaves.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Michele Tanner (941-894-5603)
4350 CHATHAM DR #105, LONGBOAT KEY, FL 34228
$310,00031 Days on yellowkey MLS ID: A4697241
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,147 Tax: $1,457 (2025)Community: Longboat HarbourCondo
Taxes:$1,457
Remarks: Exceptional opportunity to own a beautifully furnished waterfront residence in a gated, amenity-rich boating community. This one-bedroom unit features hurricane-impact sliding glass doors and windows, allowing abundant natural light while providing peace of mind. Enjoy waterfront living with access to a private beach located at 4415 Gulf of Mexico Drive, complete with gated parking, indoor facilities, and beachside amenities. Residents have access to an impressive array of community features, including four heated swimming pools, a spacious fitness center, pickleball courts, tennis courts, kayak and bicycle storage, and a vibrant boating community with first-come, first-served boat slips. Additional amenities include a banquet hall and numerous social and recreational opportunities. Whether you're seeking a full-time residence, seasonal retreat, or investment property, this waterfront gem offers the perfect combination of coastal lifestyle, convenience, and value.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Malihe Karimi (941-376-5099)
602 SPANISH DR S #115, LONGBOAT KEY, FL 34228
$379,90059 Days on yellowkey MLS ID: A4694415
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1427 Built: 1969 Tax: $2,667 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,667
Remarks: Welcome to Spanish Main Yacht Club, one of Longboat Key's most beloved waterfront communities, where 55-plus living unfolds at an easy, unhurried pace between the Gulf of Mexico and Sarasota Bay. Tucked along a quiet street lined with tidy single-story villas and swaying palms, this fully renovated two-bedroom retreat captures the old-Florida charm that makes this island enclave so special, paired with the fresh, move-in-ready updates. Behind the arched front entry and crisp white stucco exterior with its white tile roof, a bright open interior welcomes you, where neutral tile floors run throughout and natural light pours through plantation-shuttered windows. The renovated kitchen is the heart of the home, outfitted with white shaker cabinetry, quartz countertops, a waterfall-edged peninsula, a soft glass-tile backsplash, and crisp white appliances, all opening to a generous living and dining area finished with crown molding and an easy coastal feel. A versatile bonus room wrapped in windows, with a door to the back patio, makes a wonderful sunroom, reading retreat, or home office. Both bedrooms are comfortable and well-appointed, served by two beautifully updated bathrooms, one with a tub and shower framed in subway tile, the other a glass walk-in shower with a mosaic floor and designer fixtures. A covered carport with room for a golf cart, plus interior storage for kayaks and beach gear, adds everyday ease. Brick paver walkways and lush tropical landscaping wrap the home, and the concrete tile roof is just over five years young. Life at Spanish Main is built around the water and the warmth of neighbors. Residents enjoy a heated pool overlooking the basin, a clubhouse, shuffleboard courts, kayak storage and launch, and a deep-water marina with boat slips available for a monthly fee, offering quick access to Sarasota Bay and the Gulf beyond. Best of all is the community's private Gulf beach access, just a short stroll away, along with shaded benches lining the lagoon and a waterfront green where slow mornings and golden evenings by the water become a way of life. Beyond the community, the white sand of Longboat Key's Gulf beaches is moments away, with the boutiques and dining of St. Armands Circle, downtown Sarasota's culture, and the laid-back charm of Anna Maria Island all within easy reach. Come experience the rare blend of comfort, community, and coastal beauty that makes this villa a place to call home. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
2000 HARBOURSIDE DR #1501, LONGBOAT KEY, FL 34228
$699,00026 Days on yellowkey MLS ID: A4697798
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1370 Built: 1985Monthly Fee: $1,733 Tax: $9,011 (2025)Community: Fairway Bay 2 Ph 2 & 3Spa: YesTownhouse
Taxes:$9,011
Elementary School: None
High School: None
Middle School: None
Remarks: Nestled in the attractive community of Fairway Bay in Bay Isles on Longboat Key is this fabulous 2BR/2BA elevated townhouse. This tastefully decorated condo residence is on one level above the oversized 2-car garage and is an end unit. It is beautifully maintained, in great condition and offered turnkey-furnished with upscale furnishing from Robb & Stucky. The spacious living room and dining room has high ceilings, crown molding, plantation shutters, a fireplace and a wet bar with built-ins. The updated kitchen completed in 2025 is a neutral palette with new white cabinetry, white quartz countertops, a super pull-out pantry, all new appliances and washer & dryer in the past 12 months. A/C replaced in 2020 & water heater in 2021. The flooring in the entire residence was recently replaced with luxury vinyl plank flooring. A spacious shaded screened lanai offers a peaceful garden view and is a short walk to the heated pool and the bay. The bathrooms have also been updated in 2025 with new flooring, new cabinets, fixtures and shower door. The primary bedroom suite is a quiet sanctuary offering ample room for your apparel with two walk-in closets and Hunter-Douglas window blinds. This townhouse affords plenty of room for guests and a large family to stay. There is a two-and-a-half garage with a large finished air-conditioned space on the ground floor giving you extra space. Community amenities include walking paths, 2 heated pools, a fitness room, tennis & pickle ball courts and a social room. The building will soon benefit from a new roof, which the seller has paid for. Residents benefit from on-site management and 24-hour security. Ownership includes deeded access to the private Bay Isles Beach Club, featuring a Gulf front pavilion, grilling areas, and beautiful sandy beaches. Located within the Longboat Key Club, residents have the option to join golf, tennis, and social memberships, all just minutes from the boutiques and dining on world-renowned St. Armands Circle, downtown Sarasota’s cultural attractions and Harbourside Marina.
Listing Agent: Carolyn Donnelly, Pa (941-350-9900)
1005 BOGEY LN, LONGBOAT KEY, FL 34228
$2,999,000173 Days on yellowkey MLS ID: A4680006
REDUCED by $301,000 (9.1%) on 07/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3624 Built: 2017Monthly Fee: $21 Tax: $19,847 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$19,847
Remarks: Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.
Listing Agent: Michael Nink, Pa (941-914-2805)
3010 GRAND BAY BLVD #493, LONGBOAT KEY, FL 34228
$1,475,000282 Days on yellowkey MLS ID: A4668143
REDUCED by $404,000 (21.5%) on 07/06/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1999 Tax: $16,976 (2025)Community: Grand Bay 4Spa: YesCondo
Taxes:$16,976
Remarks: One or more photo(s) has been virtually staged. Perched just one floor below the penthouse in the sought-after Grand Bay IV community on Longboat Key, this 2,550-sq.-ft. Cayman floor plan offers an exceptional opportunity to enjoy the Grand Bay lifestyle immediately. With ideal north–south exposure, this residence captures breathtaking sunrises over Sarasota Bay and stunning Gulf sunsets from two expansive terraces. Walls of glass and abundant natural light enhance the open-concept layout, which includes 2 bedrooms, 2.5 baths, and a den that can easily be reconfigured to include a walk-in closet for a 3rd bedroom. The primary suite opens directly to the Bayfront terrace, the second bedroom offers an en-suite bath and private Gulf-view balcony, and the den, kitchen, and third bedroom share access to a second terrace for effortless indoor-outdoor living. Two prime, side-by-side parking spaces on the upper main level sit conveniently next to the elevator, leading to a private elevator foyer. Residents of Grand Bay enjoy world-class amenities including 24-hour security, a clubhouse with library and game room, fitness center, tennis and pickleball courts, two heated pools and a spa, and deeded access to the exclusive Bay Isles Beach Club.
455 LONGBOAT CLUB RD #PH8, LONGBOAT KEY, FL 34228
$2,700,90023 Days on yellowkey MLS ID: A4697519
2 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2780 Built: 1990 Tax: $23,862 (2025)Community: PierreCondo
Taxes:$23,862
Remarks: Under contract-accepting backup offers. PENTHOUSE LIVING AT THE PIERRE – LUXURY GULF-FRONT RESIDENCE IN LONGBOAT KEY CLUB Welcome to The Pierre, an exclusive Gulf-front community featuring just 66 luxury residences nestled behind the private gates of the renowned Longboat Key Club. This beautifully renovated eighth-floor penthouse residence offers breathtaking panoramic views from every room, showcasing the tranquil bay waters, spectacular Gulf sunsets, and the sparkling city skyline. Designed to maximize natural light and capture the beauty of its surroundings, expansive windows frame unforgettable vistas throughout the home. Thoughtfully crafted for both everyday living and elegant entertaining, this exceptional residence features three spacious bedrooms, three-and-a-half baths, and a gourmet kitchen equipped with premium Thermador appliances, abundant cabinetry, and generous workspace for the discerning chef. The luxurious primary suite provides a peaceful retreat with stunning water views, while the additional guest suites allows for comfort and privacy for family and visitors. Residents of The Pierre enjoy an impressive collection of resort-style amenities, including: • Direct private beach access • Beachfront heated pool and spa • Fitness center • Tennis courts • Newly renovated lobby and common areas • Club gathering room and meeting facilities • 24-hour guarded security • On-site professional management Ownership also includes two private garage parking spaces, a secured storage area, and access to private guest suites available for visiting family and friends on a nominal rental basis. For those seeking an elevated lifestyle, membership opportunities at the renowned Longboat Key Club provide access to championship golf courses, world-class tennis facilities, spa and wellness services, exceptional dining venues, beach services, and a vibrant social calendar (membership subject to application and availability). Ideally located near St. Armands Circle and vibrant Sarasota, you'll enjoy convenient access to fine dining, boutique shopping, arts and cultural attractions, and some of Florida's most beautiful beaches. This is a rare opportunity to own an extraordinary Gulf-front penthouse in one of Longboat Key's most sought-after luxury communities. Schedule your private showing today and experience the unparalleled lifestyle that awaits at The Pierre.
Listing is courtesy of: REAL ESTATE BOUTIQUE LLC (941-726-8061)
Listing Agent: Maria Atkins (941-726-8061)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,000124 Days on yellowkey MLS ID: A4686552
1 Days Off yellowkey (back on 5/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1981 Tax: $6,376 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$6,376
Remarks: Under contract-accepting backup offers. Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit offers two expansive bedrooms and two beautiful bathrooms and comes fully turn-key. This unit was curated with attention to detail and functionality in mind. The kitchen offers plenty of storage, stainless steel appliances, quartz countertops and beautiful accent details. Enjoy three patios that allow for great indoor/outdoor living. Fully equipped with Hurricane impact doors and windows. One under building parking space included, along with a locked storage closet - perfect for bikes and beach gear. When not at the beach, enjoy the meticulously kept nature trails, landscaped grounds and wildlife. Just steps away from the well appointed clubhouse is equipped with a Junior-Olympic sized heated pool, four har-tru tennis courts, a fitness center and more. In addition, Bayport residents are proud of their active social and recreational calendar. Water enthusiasts can utilize the secluded fishing pier that stretches out onto Sarasota Bay; to fish, watch the sunrise, the Manatees swim or the Egrets wading among the mangrove trees. Residents also benefit from conveniently located on-site paddle board and kayak launch and storage areas. Bayport residents enjoy an array of restaurants locally, and the convenience of a nearby supermarket, pharmacy and boutique shops. Recreational enthusiasts also benefit from the nearby Bayfront Park which offers a popular pickle-ball program, dog park and other bayside activities. The nearby Longboat Key Club offers private access to championship waterfront golf, extensive leisure activities and boating facilities. Within minutes, one can access the famous St Armand's Circle with its exceptional shopping and dining amenities. From there, cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining.
Listing Agent: Alexis Smith-Frady (352-225-1724)
3271 BAYOU RD, LONGBOAT KEY, FL 34228
$1,995,00044 Days on yellowkey MLS ID: TB8515918
0 Days Off yellowkey (back on 7/7/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3059 Built: 2014Monthly Fee: $104 Tax: $27,748 (2025)Community: Bay IslesSingle Family
Taxes:$27,748
Remarks: Under contract-accepting backup offers. Nestled behind the gates of prestigious Bay Isles on Longboat Key, this exceptional residence offers over 3,000 square feet of thoughtfully designed living space surrounded by lush tropical landscaping and just moments from the Gulf of Mexico. Combining timeless architecture, spacious interiors, and resort-style outdoor living, this home delivers the privacy and elegance that define the Longboat Key lifestyle. A grand entry welcomes you into an open and inviting floor plan featuring soaring ceilings, abundant natural light, and generous living and entertaining spaces. The expansive great room flows seamlessly into the dining area and well-appointed kitchen, complete with ample cabinetry, extensive counter space, and a convenient wet bar for effortless entertaining. The first-floor primary suite serves as a private retreat with a spacious bedroom, large walk-in closet, and luxurious en-suite bath. Additional guest bedrooms are thoughtfully positioned for privacy and comfort, while the second floor offers a private guest suite with balcony access—perfect for visitors seeking their own space and enjoying tropical views. Designed for year-round enjoyment, the screened outdoor living area is a true highlight. Relax poolside in the sparkling heated pool and spa, entertain under the covered lanai, or unwind amidst the lush tropical surroundings that create a secluded backyard oasis. Located within the highly sought-after Bay Isles community, residents enjoy 24-hour gated security, beautifully maintained grounds, and exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Just minutes away are the Longboat Key Club's championship golf courses, tennis facilities, marina, waterfront dining, boutique shopping, and renowned St. Armands Circle. Offering the perfect blend of luxury, privacy, and coastal convenience, this exceptional Longboat Key residence presents a rare opportunity to enjoy one of Sarasota's most desirable island lifestyles.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Robert Johnson (813-364-2250)
2600 HARBOURSIDE DR #R9, LONGBOAT KEY, FL 34228
$335,000328 Days on yellowkey MLS ID: A4661661
Bed: Bath: 0.0 Monthly Fee: $498 Tax: $3,260 (2025)Community: Longboat Key MooringsDock-Rackominium
Taxes:$3,260
Remarks: Embrace Unparalleled Elegance: Exquisite 75’ Boat Slip on Longboat Key’s premier R dock, Your Gateway to a Refined Gulf Coast Yachting Experience. Discover the pinnacle of luxury boating with this stunning 75’ x 21’ deep water boat slip, perfectly situated on the spectacular R dock at Longboat Key Club Moorings Marina, nestled along Florida’s breathtaking Gulf Coast. Slip R-9 offers unrivaled views and the closest proximity to the inlet for effortless navigation, with serene waters and vibrant sunsets and the spectacular Sarasota sky line across the bay, as your backdrop—a gateway to an extraordinary yachting lifestyle. Located on Longboat Key, Slip R-9 provides direct access to the Intracoastal Waterway, ideal for deep-sea fishing or leisurely cruises. Enjoy upscale conveniences like Publix, CVS, Chase Bank, a post office, and public tennis courts just moments away. A complimentary shuttle connects you to the chic boutiques and gourmet dining of St. Armands Circle, while you can easily boat to iconic North Longboat Key restaurants like The Shore and Mar Vista, or nearby favorites like Chart House and Dry Dock Waterfront Grill, where fresh seafood and stunning views await. Longboat Key Club Moorings Marina is renowned for its elegance, offering high-speed Wi-Fi, water, laundry facilities, and pump-out services for a seamless experience, with pristine facilities and attentive staff catering to your every need. Visit by boat the nearby sandbars for leisurely afternoons in turquoise Gulf waters, or opt for membership to the Bay Isles Beach Club or Longboat Key Club for access to pristine, sandy beaches and world-class amenities. Unlike other slips, R-9 is not covenanted, meaning Longboat Key Club membership is optional, giving you the freedom to tailor your lifestyle with access to championship golf courses or the exclusive beach club at your discretion. Slip R-9 is more than a boat slip, it’s an invitation to a coastal lifestyle, with quick access to open waters, dining destinations like The Shore and Mar Vista, magical sandbars, and elite recreational opportunities. Own a piece of paradise in this A+ location, where every detail is designed for elegance and ease. Pursuant to condo rule this slip will accommodate a yacht with LOA of 70ft and 17ft beam and will be subject to association approval.
Listing Agent: Mark J Baron, Llc (941-241-7633)
600 SUTTON PL #101B, LONGBOAT KEY, FL 34228
$335,000479 Days on yellowkey MLS ID: C7507243
REDUCED by $14,900 (4.3%) on 07/07/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 883 Built: 1973Monthly Fee: $1,232 Tax: $6,247 (2024)Community: Sutton PlaceCondo
Taxes:$6,247
Remarks: Waterfront condo with Sarasota Bay views! Perfectly positioned along Sarasota Bay on **Longboat Key** and just steps from the turquoise waters of the **Gulf of Mexico**, this exceptional community offers the ultimate coastal lifestyle in an unbeatable location. Current owners have never had water intrusion from any hurricanes. This spacious ground-floor corner residence features an expansive open-concept layout designed to comfortably accommodate up to six guests. The beautifully remodeled kitchen showcases stainless steel appliances, a brand-new range, granite countertops, stone backsplash, recessed lighting, and solid wood cabinetry — blending modern style with everyday functionality. A charming nook provides the perfect space for additional sleeping accommodations or a cozy retreat to enjoy serene bay views. Impact-rated sliding glass doors open seamlessly to the outdoors and are complemented by brand-new Shade Store cellular window treatments. Relax while taking in peaceful water and pool views from the comfort of your living space. The spacious primary bedroom features custom cellular shades with top and bottom openings to maximize natural light and views, along with a walk-in closet complete with built-ins. The ensuite bath has been thoughtfully updated with a newer vanity and a brand-new shower remodel (2025), offering a fresh, modern feel. Furnishings are optional and tastefully curated with designer touches, making this property move-in or rental ready. Exceptional Community Amenities - Residents enjoy a truly unique waterfront lifestyle: Two heated pools, Marina and clubhouse, Available boat slips for rent, Fish-cleaning station, Kayak storage with electric launch, BBQ grilling areas, Car wash station, Lighted assigned carport parking, Elevator access, Private storage unit (3rd floor), Laundry facility (2nd floor), Exclusive deeded beach access on Longboat Key, featuring a pavilion, storage lockers, indoor showers, and restrooms. Enjoy watching dolphins and manatees from the bayfront grounds, spend your days fishing or kayaking, or relax on the sugar-sand beaches just across the street. The community is also in the planning stages of adding a brand-new state-of-the-art fitness center. Shopping and dining are just minutes away at the renowned **St. Armands Circle**. Experience the best of both worlds — Gulf-front beach days and tranquil bayfront evenings. This is coastal living at its finest.
Listing is courtesy of: MARINA PARK REALTY LLC (941-205-0888)
Listing Agent: Jill Baldwin (941-223-2025)
435 L AMBIANCE DR #L807, LONGBOAT KEY, FL 34228
$3,200,000281 Days on yellowkey MLS ID: A4668015
REDUCED by $300,000 (8.6%) on 05/14/2026
Bed: 2 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2525 Built: 1994 Tax: $29,083 (2024)Community: L Ambiance At Longboat Key Club Ph 02Spa: YesCondo
Taxes:$29,083
High School: Riverview High
Middle School: Pine View School
Remarks: Sunrise to Sunset Views - Your Coastal Paradise awaits you at L'Ambiance!** 2 bedrooms with an open den --step into a world of instant enjoyment. Nestled along the stunning Gulf of Mexico, L'Ambiance offers you a front-row seat to Sarasota's dramatic sunrises and captivating sunsets. This exceptional corner residence is a rare gem, designed to help you create a lifetime of cherished memories. As you glide off your private elevator into the foyer, prepare to be mesmerized by panoramic views that seamlessly blend the indoors with the stunning outdoors. Meticulously crafted by a professional decorator, this residence is a masterpiece of elegant living, featuring expansive glass walls that invite the beach's natural beauty into your home. Enjoy the custom kitchen and luxurious bathrooms, all adorned with travertine flooring in the main living areas and plush carpeting in the bedrooms. Imagine sipping your morning coffee on the east terrace, soaking in the breathtaking sunrise, or toasting to the magical afterglow of sunset with a glass of champagne on the southwest terrace. This spacious 2-bedroom (plus den or 3-bedroom) and 3.5-bathroom residence exemplifies the pinnacle of beachside luxury. Your maintenance fee ensures a stress-free lifestyle, covering everything from the building's exterior and cable service to flood insurance and on-site management so that you can immerse yourself fully in the extraordinary island living experience. With concierge services, a resort-style pool and spa, guest suites for visitors, and a state-of-the-art fitness center, L'Ambiance offers amenities that elevate your everyday life. Sarasota's pristine white, sugar-sand beaches are just the beginning! Dive into a vibrant cultural scene to enjoy the Sarasota Opera, the Sarasota Ballet, and the West Coast Symphony. Explore the renowned Ringling Museum of Art, wander through charming art galleries and antique shops, or indulge in exquisite dining at world-class restaurants. Whether you crave the excitement of marinas and golf courses or the casual charm of local cafes, Sarasota truly has it all. Make this luxurious beachfront residence your new home and embrace the unparalleled lifestyle that awaits you at L'Ambiance. Your dream of extraordinary living is just a step away!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
600 PUTTER LN, LONGBOAT KEY, FL 34228
$9,400,000562 Days on yellowkey MLS ID: A4633484
REDUCED by $1,100,000 (10.5%) on 05/19/2026
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5982 Built: 2017Monthly Fee: $17 Tax: $69,287 (2025)Community: Country Club Shores, Unit 5, Sec 3Spa: YesSingle Family
Taxes:$69,287
Remarks: Welcome to Paradise on Longboat Key. This coastal modern home is located on the direct bayfront with a total of 270 feet of waterfront on an oversized lot consisting of 18,290 square feet. As you enter the home, your first view is a serene and expansive view of Sarasota Bay all the way from the Ringling Museum to Downtown Sarasota and the Ringling Bridge. Enjoy different types of boating as the dock includes 2 jet ski lifts and a 13,000 pound boat lift. With plenty of interior space, there are 5 bedrooms and 5 baths plus a dedicated office/den, family room and game room. Every bedroom is filled with bay views. As an added advantage, guests have their own space upstairs that includes a kitchenette. Outfitted with an elevator that stops at every floor, including the three car garage, convenience is just a step away. To enjoy the views outside, there is an outdoor surround lanai with disappearing screens, fireplace and summer kitchen. Large covered terraces on both levels provide views of beautiful sunrises over Sarasota Bay and Downtown Sarasota.
Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)
Listing Agent: Kathleen Callender (941-321-3115)
541 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$830,00081 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.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
669 SPANISH DR N #21, LONGBOAT KEY, FL 34228
$335,000417 Days on yellowkey MLS ID: A4653816
0 Days Off yellowkey (back on 7/6/2026)
REDUCED by $4,000 (1.2%) on 06/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1087 Built: 1969 Tax: $5,733 (2024)Community: Spanish Main Yacht Club CondoCondo
Taxes:$5,733
Remarks: Virtually Staged. Priced to sell - Fully renovated villa ready for immediate occupancy! Welcome to Spanish Main Yacht Club, a sought-after 55+ waterfront community on Longboat Key, where coastal living meets exceptional value. This 2-bedroom, 2-bath villa-style condo offers 1700 SqFt of interior living space, 1087 of it under air, with endless potential to make it your dream home. This stand-alone condo has undergone FEMA-approved storm mitigation and a full rebuild. Bring your vision and decorate to suit your personal style—below market value! Step inside to find a spacious open-concept living and dining area, perfect for entertaining. The adjoining Florida room offers additional flexible space, bathed in natural light—ideal for morning coffee or quiet evenings. The primary suite features an en-suite bathroom, closet and indoor laundry room. Enjoy private beach access just steps away, or take advantage of the community marina with first-come, first-served boat slips, kayak racks, and direct access to Sarasota Bay. Amenities include a heated outdoor pool, shuffleboard courts, a clubhouse with game room, library, and frequent community events. This pet-friendly community offers covered carport parking, guest spaces, and maintenance-free living, all set within beautifully maintained, palm-lined grounds. Just minutes from St. Armand’s Circle and Anna Maria Island, this location offers world-class shopping, dining, and entertainment, plus access to some of Florida’s finest white sand beaches. Whether you're looking for an investment, full-time residence or a vacation getaway, this villa offers endless potential in one of Longboat Key’s most desirable communities. Seller says bring offers—don’t miss your chance to own a piece of paradise!
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
651 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$835,000171 Days on yellowkey MLS ID: A4680514
REDUCED by $10,000 (1.2%) on 07/06/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2242 Built: 1974 Tax: $18,621 (2024)Community: Longboat KeySingle Family
Taxes:$18,621
Remarks: PRICE IMPROVEMENT!! Canal-front 3-bedroom, 2-bath home with an attached 1-bedroom, 1-bath apartment above the garage with private entrance, offering 2,242 square feet of total living space. The property has completed remediation and is ready to be rebuilt to suit your needs. Features include high ceilings, a 2-car garage, and a generous ¼-acre lot. Canal offers direct access to Sarasota Bay with no bridges. Conveniently located minutes from marinas, dining, and shopping, with easy access to St. Armands Circle, downtown Sarasota, and Anna Maria Island. Bring your personal touch to recreate this gem or start new and build the home you've always wanted on this 124 ft wide lot. A property with exceptional location and potential.
Listing is courtesy of: ALLEGIANT REAL ESTATE GROUP (941-685-3958)
Listing Agent: Lori Campbell (941-685-3958)
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