Location: Longboat Key
Do Not Show Listings
2550 HARBOURSIDE DR #333, LONGBOAT KEY, FL 34228
$1,495,000 MLS ID: A4678404
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 3067 Built: 1990Community: Marina BayCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
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Remarks: Set within a living canopy of mangroves and coastal trees, this BAYFRONT residence invites a more immersive relationship with Sarasota Bay—where filtered light, birdsong, and gentle water movement define everyday living. Behind the gates of Bay Isles on Longboat Key, this approximately 3,000-square-foot waterfront residence offers the ease and scale of a single-family home with the security and convenience of condominium living. With three bedrooms and two-and-a-half baths, the layout lives expansively, enhanced by abundant storage and thoughtful separation of living spaces. Floor-to-ceiling glass sliders in the main living areas and primary suite face east, capturing peaceful sunrise light over Sarasota Bay in a setting best described as park-like waterfront—where mature coastal trees frame the water, creating a serene, private “treehouse” ambiance. Boats glide through the mangrove preserve and lagoon toward open bay waters, accompanied by birdsong and rustling leaves. Two balconies extend the living space outdoors, including a nearly 400 sq ft screened lanai ideal for relaxed coastal living. The primary suite features bay views from bed, terrace access, dual walk-in closets, and a spa-like bath with a freestanding soaking tub, dual vanities, and a glass-enclosed shower. The second and third bedrooms share access to a west-facing balcony, offering sunset light and cross-breezes. The kitchen is both functional and social, featuring quartz countertops, a Sub-Zero refrigerator, generous prep space, a built-in desk nook, mini-fridge and wet bar—well suited for entertaining or casual mornings. A dedicated walk-in laundry room adds practicality with a butcher-block workspace, hutch, and tool cubby. Comfort and peace of mind are prioritized with two A/C zones, new condensers (2025), and two hot water tanks (2021) equipped with a flood-stop device. Brand new carpet and paint. Additional highlights include air-conditioned storage, one assigned garage parking space, and exceptional closet capacity—five linen closets, three pantry closets, and three walk-in closets. Residents enjoy on-site management, a fitness center, tennis and pickleball courts, a heated resort-style pool, car washing area, and EV charging stations. The building features a brand-new roof completed in 2025. Pet-friendly. The location is as compelling as the home itself: secure, serene, and walkable. Adjacent to the Longboat Key Club Marina, and just blocks from Publix, CVS, the post office, and banking, this location allows for a genuinely walkable daily rhythm—rare on Longboat Key. As part of Bay Isles, residents also enjoy access to the Bay Isles Beach Club, a private Gulf-front retreat with gated parking, pavilions, grilling areas, restrooms, and seating for sunset views. Deeded beach access ensures a premier spot on the sand. Membership to the nearby Longboat Key Club is available, offering championship golf, world-class tennis, a full-service spa and wellness center, waterfront dining.
Listing is courtesy of: INVESTMENTS IN SARASOTA (941-894-6059)
Listing Agent: Lee Mirman (941-587-0740)
635 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$2,895,000 MLS ID: A4679064
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3047 Built: 2025Community: Mary Regina ReeseSingle Family
Remarks: This gorgeous modern, elevated new 2025 masterpiece on fabulous Longboat Key has just made a significant price reduction! Built to the utmost of standards by the owners vision for his own family, (he is a also builder), this home has it all. Let’s start with the heavy custom front door surrounded by gorgeous large scale tiles in colors of the sea, that opens to the expansive great room, dining area and huge chefs kitchen. The kitchen is an entertainers dream, with a 5 burner gas range, pot filler, double ovens, built-in microwave and full size side by side refrigerator/freezer. A large center island provides ample storage and incredible work space, and of course there is a walk-in pantry and a separate area for a coffee and a wine fridge. Off of the kitchen and living/dining area is a screened in porch with a full outdoor kitchen for outdoor dining as well as an open porch with steps to the lush green grass. The primary suite is on this level, and a half bath and a gorgeous ensuite. The ensuite features an abundance of light with double sinks, a large double shower and a soaking tub. When you head up the staircase to the 2nd level, you will certainly notice the continuance of the incredible finishes and modern original light fixtures! Here you find a large landing with sliders to the enticing outdoor deck, perfect for your morning workout overlooking the beautiful neighborhood or just a spot for some sunset sky watching or midnight stars. 3 bedrooms, two with a jack and jill and one with a full ensuite make easy use of the space for all of your family and friends. Room for a pool on the side yard, plus deeded beach access across Gulf of Mexico Drive, make this a contemporary beach house to remember! This special, walkable mid-key location puts multiple dining, shopping and wildlife exploring destinations right at your doorstep, but you also have the opportunity for the world-renowned St.Regis Resort, St. Armands Circle and the cultural epicenter of Downtown Sarasota within a short drive. This is truly a lifestyle worth exploring. Make your private appointment today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4440 EXETER DR #301, LONGBOAT KEY, FL 34228
$595,000 MLS ID: A4684917
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970Community: Longboat HarbourCondo
Remarks: 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)
3710 GULF OF MEXICO DR #E3, LONGBOAT KEY, FL 34228
$175,000 MLS ID: A4592507
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 680 Built: 1983Community: Gulfshore Of Longboat KeyManufactured Home
Remarks: JUST ELEVATED! Gulfshore of Longboat Key, Inc. offers it all. It extends from the Gulf of Mexico to Sarasota Bay. It has approximately 450- 500 feet of frontage on the Gulf, a marina on Sarasota Bay, a large heated community pool, fabulous club house with a commercial kitchen and much more. It is one of the best kept secrets on Longboat. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armands Circle with fabulous shopping and gourmet restaurants. This unit was manufactured in 1983 and has sustained damage from the two recent hurricanes. All water damage has been addressed. (Please note, parts of this listing describe the interior layout as it was before flooding). The interior is now a blank canvass allowing the buyer to design their own layout. This home previously featured a large living room, kitchen, dining room, two bedrooms, and a full bathroom. It also has a separate bath house/bathroom (requires remodeling) with a shower that is perfect for when you return from the beach. The driveway can accommodate two cars. Most importantly, the unit has been elevated to four feet and a new electric feed has been installed. In addition, new steps have been built for the front entrance. Gulfshore is a 55+ community and does not permit rentals or pets. This home, combined with the amenities offered by Gulfshore and the surrounding area, will make it easy for you to own a piece of paradise on Longboat Key.
Listing is courtesy of: EDGEWATER REAL ESTATE, INC (941-778-8104)
Listing Agent: Bill Shuttleworth (941-779-8877)
5055 GULF OF MEXICO DR #421, LONGBOAT KEY, FL 34228
$575,000 MLS ID: A4684543
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973Community: Club Longboat Beach & TennisCondo
Remarks: Set within the highly regarded Club Longboat Beach & Tennis on Longboat Key, this 2BR/2BA residence offers an excellent opportunity to create something truly special in one of the island’s most amenity-rich communities. Just under 1,500 sq. ft. and located on the second level, the residence enjoys a comfortable layout where the primary suite opens to a private terrace, bringing in light and breezes throughout the day. The dining area features a tray ceiling and flows easily into the living room, where a full wall of sliders leads to an open terrace and invites indoor and outdoor living to blend naturally. The space is ready for your personal design vision, offering a solid canvas in a location where lifestyle often takes center stage. Life at Club Longboat Beach & Tennis is known for its mix of recreation, flexibility and beachfront access. Residents enjoy 750 feet of pristine shoreline, eight Har-Tru tennis courts, pickleball courts, two heated pools, a fitness center and a relaxed, social atmosphere. Pet-friendly with 2 pets, no weight restrictions and a rental policy allowing one-month minimum stays up to twelve times per year, this residence is ideal for a full-time escape, seasonal retreat or investment opportunity.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
519 ROUNTREE DR, LONGBOAT KEY, FL 34228
$6,488,000 MLS ID: A4674266
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3554 Built: 2025Community: Longboat Key EstatesSingle Family
Remarks: BUILT TO LAST. 519 Rountree is new construction built entirely of concrete block (CBS) across every level—unlike many barrier island homes that transition to wood-frame construction above the flood elevation. The residence has already experienced recent hurricanes without damage. NEW CONSTRUCTION. 519 ROUNTREE is a privately positioned coastal residence offering over 6,400 square feet of indoor and outdoor living, including approximately 5,200 square feet under roof and a 1,100 square foot elevator-accessible rooftop terrace, located within Longboat Key Estates. GULF LIVING EXPERIENCE. At 519 Rountree, days begin with morning air carrying the salt-kissed character of the Gulf and conclude with glowing sunsets that define the Florida coastline. This is not simply proximity to the beach — it is immersion in it. Positioned just moments from the sand, the home offers balcony and rooftop experiences designed for sunset entertaining, open-air dining, and the effortless rhythm of Gulf living from morning through evening. WATERFRONT LIVING. A waterside deck is currently in process, transforming the canal setting into a true extension of the home’s outdoor living experience, subject to permitting. Flexibility remains for a variety of dock and lift configurations, tailored to buyer preference. DESIGN AND EXECUTION. The newly constructed residence has withstood three recent hurricanes without damage, a testament to its quality, elevation, and thoughtful execution. Each level is purposeful in both design and function, delivering a vertical lifestyle that feels intuitive, private, and refined. FURNISHINGS. For buyers seeking the residence exactly as photographed, the complete furnishings and curated design package may be acquired separately. FINAL NOTE. 519 Rountree delivers the atmosphere buyers seek when they say they want Gulf living — quietly, privately, and without excess.
Listing is courtesy of: IRVING GROUP INC (305-900-2100)
Listing Agent: James Irving (813-843-2979)
2600 HARBOURSIDE DR #R9, LONGBOAT KEY, FL 34228
$335,000 MLS ID: A4661661
Bed: Bath: 0.0 Community: Longboat Key MooringsDock-Rackominium
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 is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Mark J Baron (941-241-7633)
1065 GULF OF MEXICO DR #305, LONGBOAT KEY, FL 34228
$1,299,000 MLS ID: A4681609
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1819 Built: 1981Community: Beachplace IiiCondo
Remarks: One or more photo(s) has been virtually staged. A vivid palette of white perfected with the backdrop of crystal sand meets azure Gulf blue….. finished off with brilliant hues over the spanning skies as the sun sets on yet another perfect day. Yours to be experienced daily, from the inside or out on the patios, at this corner condo home spread over more than 1,800 square feet. Well-positioned at the southwest corner of Building 10 to take full advantage of what it means to be the fortunate owner of a beachfront Longboat Key retreat. Clean, crisp and white, this home is move-in ready, OR it is fresh and primed for you to begin the design of your dreams. Finding 3 bedrooms, 2 baths, and 2 owned parking spaces (one under-building and one outside steps to the building entry) on the beach at this reasonable price point is a FIND in this zip code, so closely consider the opportunity at hand. Beachplace is a sprawling community of 31 acres and full of amenities including, but not limited to, deeded beach access, junior Olympic size pool, kiddie pool, spa, clubhouse, fitness, tennis, pickleball, guarded/ gated entry, community grilling, fun gaming area with ping pong, cornhole, seasonal community activity calendar, etc. Truly a special place to call home or an absolute escape to refresh, restore, relax, release and renew the wellbeing of mind, body and spirit.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Cindy Schatzle (941-587-7556)
836 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$995,000 MLS ID: A4674750
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2813 Built: 1991Community: Cedars East Sec 3Condo
Remarks: Introducing a Cedars East condominium unit offering the space and privacy of a single-family home with the ease of condo living. Elevated among the treetops on the Bay side of the island, the home enjoys partial Sarasota Bay views and exceptional access to the water perfect for launching a kayak, fishing, enjoying the tide pools. This premier tennis community home features 2 garage spaces, wood floors throughout the first elevated floor, a bright, open great room with a large open kitchen for entertaining, with water views of Sarasota Bay, and inviting fireplace, screened decks for bay breezes, and an office/den. Upstairs is the primary bedroom with multiple walk-in closets, ensuite bathroom and screened porch where you can unwind and catch a glimpse of the sunset glow over the treetops. Two guest bedrooms share a full bathroom. Offered furnished. Cedars East is filled with amenities. From the clubhouse with a restaurant and Tiki Bar, pool, to walking trails through the mangroves, a kayak launch and a bayside community pier for gathering, fishing and enjoying the sunrise. A tennis club membership allows access to tennis and pickleball courts, tournaments and more. There's even an onsite tennis pro if you need lessons. Joan Durante Park Community Park and the Gulf beaches are nearby. What are you waiting for? Make this your home today.
Listing Agent: Eileen Saunders (662-404-0816)
585 SANCTUARY DR #B502, LONGBOAT KEY, FL 34228
$1,699,000 MLS ID: A4679102
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1823 Built: 1990Community: Sanctuary ICondo
Remarks: Perched on the fifth floor of Building 1 at The Sanctuary at Longboat Key Club, this corner residence offers sweeping views that extend from the Gulf of Mexico across the Longboat Key Club golf course to Sarasota Bay and the downtown skyline. A wraparound terrace enhances the setting, creating an exceptional indoor-outdoor experience with ever-changing light and scenery throughout the day. Inside, the open floor plan spans nearly 1,900 square feet and is designed to maximize both comfort and function. Walls of glass sliders in multiple rooms open directly to the terrace, allowing for sunset views, fresh coastal breezes, and natural light to flow throughout the residence. The living and dining areas connect seamlessly, providing an ideal layout for everyday living or entertaining. The primary suite is privately positioned and features oversized windows framing sun-filled views, a walk-in closet, and an en-suite bath. Two additional bedrooms are each en-suite, offering flexibility for guests, family, or a home office while maintaining privacy for all. Three full baths complete this thoughtfully arranged residence. Additional conveniences include one secure, under-building parking space and a dedicated storage unit. Residents of The Sanctuary enjoy a full complement of resort-style amenities, including a Gulfside swimming pool with cabanas, expansive sundeck, outdoor bar, and an additional heated pool and spa. Tennis courts, a modern fitness center, and a variety of clubhouse activities enhance the Longboat Key lifestyle. A private boardwalk provides direct access to the pristine beach, while a 24-hour manned guard gate and on-site management ensure peace of mind. Ownership also offers the option to join the renowned Longboat Key Club, available separately, granting access to championship golf, premier tennis facilities, marina services, spa amenities, dining venues, and resort-style social offerings. Ideally located on Longboat Key, The Sanctuary places you minutes from waterfront dining, boating, and shopping. St. Armands Circle, Lido Beach, and downtown Sarasota’s theaters, galleries, and cultural attractions are all within easy reach—offering a refined coastal lifestyle where natural beauty and convenience meet.
Listing Agent: Roger Pettingell (941-387-1840)
2110 HARBOURSIDE DR #547, LONGBOAT KEY, FL 34228
$929,000 MLS ID: A4681901
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2105 Built: 1988Community: Fairway Bay 3Condo
Remarks: Experience refined coastal living behind the gates of the prestigious Bay Isles. This beautifully appointed 3-bedroom, 2-bath residence in The Atrium offers an exceptional blend of elegance, comfort, and convenience just minutes from St. Armands Circle and vibrant downtown Sarasota. Designed for effortless living and entertaining, the open floor plan showcases high ceilings, a sophisticated blend of tile and wood flooring, and expansive walls of glass sliders that bathe the interior in natural light. The spacious terrace captures panoramic views of Sarasota Bay and the sparkling city skyline, an idyllic backdrop for breathtaking sunrises and tranquil evening reflections. The primary suite is a serene retreat with direct terrace access, dual walk-in closets, and a spa-inspired en-suite bath featuring dual vanities, a soaking garden tub, and a glass-enclosed walk-in shower. Two additional guest bedrooms provide comfort and privacy, each with private balcony access, ideal for hosting family and friends. Additional highlights include secure garage parking and a private storage unit. The home offers a newer high-end HVAC system with UV germicidal light and integrated dehumidifier, plus a newer hot water heater for added reliability. Hurricane shutters and smart home features allow remote controls of shades, lighting, ceiling fans, and thermostat for efficiency and peace of mind. Residents enjoy 24/7 security through Bay Isles, adding comfort and exclusivity. Residents enjoy exclusive access to the Bay Isles Beach Club, located just across from the community, offering a private Gulf-front beach, restrooms, covered picnic areas, barbecue grills, and a volleyball court. The Atrium enhances the lifestyle further with a heated swimming pool, tennis and pickleball courts, clubhouse, fitness center, and on-site management. This is a rare opportunity to own a bay-view residence in one of Longboat Key’s most sought-after gated communities, where luxury meets relaxed coastal sophistication.
Listing Agent: Mimi Kruk (941-587-5188)
2295 GULF OF MEXICO DR #23S, LONGBOAT KEY, FL 34228
$1,395,000 MLS ID: A4669226
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970Community: Islander Club Of LongboatCondo
Remarks: Set directly on the shores of the Gulf of Mexico, this beautifully renovated residence in the Islander Club captures the essence of Longboat Key beachfront living. Located in the desirable South Tower, this 2BR/2BA home showcases a fresh coastal design with wide-plank flooring, crown molding, recessed lighting, and an open layout oriented to the water. The kitchen exudes coastal charm with stone countertops, shaker cabinetry, stainless-steel appliances, and a sea-glass tile backsplash. Both baths have been redone with refined finishes, glass-enclosed showers, and clean modern tilework. Floor-to-ceiling sliders open to an expansive covered terrace—perfect for outdoor dining, lounging, and taking in sweeping Gulf views. The primary suite also enjoys terrace access and an endless horizon of turquoise water. Residents of the Islander Club enjoy 400 feet of private beach, a Gulf-front pool, fitness center, tennis courts, pickleball, library, social lounge, and on-site management within two secure towers and gated entry. The recently updated common areas - including the elegant lobby and clubroom - offer a stylish, contemporary ambiance overlooking the Gulf. Ideally positioned near St. Armands Circle and Sarasota’s world-class dining, shopping, and cultural attractions, this residence offers an effortless blend of comfort, sophistication, and beachfront tranquility.
2295 GULF OF MEXICO DR #115S, LONGBOAT KEY, FL 34228
$895,000 MLS ID: A4670081
Remarks: Wonderful "Manhattan Style" beachfront Condo with sweeping views of Sarasota Bay and views of the Gulf now available at the popular Islander Club on LBK. This gorgeous beachfront renovation was completed 4 years ago and truly shows all the craftmanship that went into the process under the owner's direction. Open kitchen beings the morning light into the room for enjoying your coffee or tea as you gaze across the sparking blue waters of the bay. Large 38ft balcony also has views of bay and a bit of the Gulf of Mexico. The Primary suite is a comfortable 13X20 which accesses the balcony and has a large walk-in closet. It is light and bright and a restful haven away from the main living area. The Islander club has recently renovated their clubhouse. The gym overlooks the gulf and the pool. There is a conference room, library, and an Olympic size heated pool, not to mention their Har-Tru tennis courts. The Location is very convenient. The shops of Bay Isles with the Publix and CVS are just a couple of minutes away. It's only 10 minutes to World renown St Armand Circle. Make this your permanent home or your week-end getaway. Secured Building . At The Islander Club "Everyday is a Holiday and Life is an endless vacation.
Listing Agent: Michael Nink, Pa (941-914-2805)
1920 HARBOURSIDE DR #1003, LONGBOAT KEY, FL 34228
$684,500 MLS ID: TB8462750
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1590 Built: 1982Community: Fairway Bay 1Townhouse
Remarks: Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Connor Meckley (941-279-0013)
4350 CHATHAM DR #105, LONGBOAT KEY, FL 34228
$349,900 MLS ID: A4670294
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Community: Longboat HarbourCondo
Remarks: Welcome to your Affordable slice of Paradise with Potential Rental Income. Move-In-Ready, One Bedroom One Bath, updated waterfront unit located mid-key, in the desirable community of Longboat Harbour. This coastal unit overlooks the bayou leading to Sarasota Bay. From the minute you enter the unit, you feel the resort lifestyle. The enclosed lanai offers views with fabulous breezes when opening the doors and allowing tranquility to set in. Sip your coffee or beverage, listen to the birds, and enjoy the view of the bayou. This cozy unit is located on the ground floor, conveniently located next to the mailboxes, laundry room, and elevator. It also boasts views from every room. The Neutral color palette offers plenty of imagination for your decorating style. This special community has an array of activities for your enjoyment. Exclusive access is controlled by a gated entrance, deeded beach access, including indoor facilities. If swimming is your passion, there are FOUR heated swimming pools throughout the lush property. The amenities include an awesome fitness center, pickleball, tennis, a banquet hall, spacious dance floor. Additional perks are a library, art studio, billiard room, private storage, assigned covered parking, and plenty of guest parking. There are NO Special assessments in the works! Pack your bags, dancing shoes, and enjoy a carefree, active, affordable coastal lifestyle! Schedule a Showing Today!
Listing Agent: Dia Wilson (941-284-3667)
530 CHIPPING LN, LONGBOAT KEY, FL 34228
$5,799,000 MLS ID: A4685275
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 4216 Built: 2026Community: Country Club Shores Sec 02Single Family
Remarks: Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure, tranquil canal views create a peaceful backdrop to daily living, while upper balconies frame beautiful views of Sarasota Bay. The home’s architecture, floor plan, and interior selections were curated by Brista’s in-house design team, drawing on years of experience building on Longboat Key and a deep understanding of what today’s waterfront buyers value most—timeless architecture, premium materials, and seamless indoor-outdoor living. A handcrafted iron pivot entry door framed by natural stone detailing creates a striking first impression. Inside, pocketing glass doors open the main living spaces to a resort-style outdoor setting where a custom salt water pool and elevated heated spa are surrounded by porcelain pavers and lush coastal landscaping. A fully equipped outdoor kitchen creates the ideal setting for entertaining along the water. At the heart of the home, the kitchen blends refined design with exceptional functionality. Custom Italian cabinetry is complemented by a dramatic Quartzite waterfall island and matching hood feature. A premium appliance suite by Miele — including a built-in refrigerator, integrated dishwashers, speed oven, and built in coffee maker — is complemented with a striking 48-inch dual-fuel range. A hidden butler’s pantry and custom wine display add both style and practicality for effortless entertaining. The great room centers around a sleek linear fireplace, creating a sophisticated gathering space. Upstairs, a spacious club room with a media wall and wet bar offers a relaxed setting for evenings with family and guests. Architectural details throughout the home include white oak plank flooring, a dramatic floating staircase, recessed baseboards, and clean modern lines that reflect a refined coastal aesthetic. Modern conveniences include whole-home audio, a whole house generator, multi-zone climate control, and integrated security. Located within one of Longboat Key’s most desirable boating communities, where deepwater canals provide quick access to Sarasota Bay and the Gulf of Mexico, this newly completed custom residence represents a rare opportunity to experience waterfront living defined by thoughtful design, exceptional craftsmanship, and enduring quality.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Gina Ursini (941-812-4894)
5840 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$4,950,000 MLS ID: A4670094
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 4145 Built: 2022Community: Longboat KeySingle Family
Remarks: Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Cooney Architects and built in 2022 by Perrone Construction, one of the Gulf Coast’s premier luxury builders, this stunning coastal residence is a rare offering that blends modern design, structural integrity, and an exceptional location. Positioned on the desirable northern end of Longboat Key, the home offers a lifestyle few can match, with both deeded beach access directly across the street and canal frontage in the backyard. Where most homes require a choice between Gulf or Bay, this property offers the best of both. Step inside to discover a layout designed for both comfort and sophistication. The main level features a serene primary suite with a spa-inspired bathroom, a seated vanity, and a custom walk-in closet. A thoughtfully planned home office includes a custom built-in desk with dual workstations, offering dedicated space for both homeowners. The open-concept living area flows effortlessly into the designer kitchen, outfitted with quartz counters, Thermador appliances, a paneled refrigerator and freezer, wine fridge, and ice maker. A hidden walk-in pantry provides additional prep space and ample storage. Upstairs, a central family lounge connects three en-suite bedrooms, two with tranquil canal views where manatees are often spotted lingering at the water’s surface. The upper level is easily accessed by both a residential elevator and a beautifully crafted staircase with integrated storage. Every room has been carefully curated to reflect the home’s effortless luxury. For buyers seeking a fully realized, move-in-ready experience, furnishings can be negotiated separately. Outdoor living is elevated with a heated saltwater pool and spa, expansive lounging and dining terraces, and a fully equipped summer kitchen featuring stone counters, a Lynx grill, and built-in refrigeration, all protected by push-button retractable hurricane shutters. A dedicated pool bath adds convenience and keeps wet feet out of the house. The private dock includes a 16,000-pound boat lift, a 4,500-pound kayak or jet ski lift, plus additional space to dock a larger vessel in the water. The dock is fully outfitted with shore power, running water, integrated lighting, and a fish-cleaning station, ready for both adventure and convenience. Built high and dry, the home remained fully protected during recent storms, a true reflection of the enduring quality behind its construction. Combining beauty, function, and peace of mind, this is a rare opportunity to enjoy the very best of Longboat Key living, free from compromise.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
2675 GULF OF MEXICO DR #403, LONGBOAT KEY, FL 34228
$1,200,000 MLS ID: A4645760
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1896 Built: 1979Community: VeinteCondo
Remarks: Under contract-accepting backup offers. A New Year is here and a New Price with gorgeous full gulf views on Longboat Key. Veinte (20 in Spanish) is a luxury condominium community with only twenty residents located on beautiful and unique Longboat Key. Magnificent direct gulf views from all main rooms; electric hurricane shutters on lanai and bedrooms, electric screen on the lanai and custom shades on all windows. Coming partially furnished (Exclusion list available) with under building parking. This unique residence that you will love once you enter and see the beautiful azure waters of the Gulf of America is waiting for some TLC or to be updated to your own personal taste. Sit on your lanai for your morning coffee or afternoon cocktail and watch the million dollar view to see the fabulous sunsets. A large swimming pool facing the Gulf and a combination tennis/pickleball court. This residence is in a great location on Longboat Key with CVS, Publix and three Banks close by and only a short distance to famous Saint Armand's Circle and downtown Sarasota where there are many restaurants and boutique shopping to enjoy along with the many amenities that Sarasota has to offer which includes the Opera, Ballet, Florida Studio Theater, many wonderful galleries just to name a few.
Listing Agent: Sandra Endres (941-735-2527)
775 LONGBOAT CLUB RD #606, LONGBOAT KEY, FL 34228
$1,450,000 MLS ID: A4666117
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1524 Built: 1984Community: Beaches Of Longboat Key Ph-1Condo
Remarks: Experience the ultimate in Gulf-front living from this beautifully positioned two-bedroom, two-bath residence in the sought-after Beaches condominium, perfectly located behind the gates of the Longboat Key Club. Wake up to unobstructed, panoramic views of the Gulf of Mexico from both bedrooms in one of the most private floor plans in the building with no neighboring balconies in sight. Enjoy peace of mind with new hurricane-impact windows and doors, recently completed as part of a building-wide upgrade. Beaches offers luxury amenities including a full-time door attendant, a beachfront pool and spa, a fitness center, tennis courts, on-site management, and secured elevated under-building parking. Just moments from the new St. Regis Resort, world-class golf and tennis, and the dining and shopping of St. Armands Circle, this is beachfront living at its best.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Chris Wetzig (941-350-8083)
70 LIGHTHOUSE POINT DR, LONGBOAT KEY, FL 34228
$13,750,000 MLS ID: A4681304
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 5475 Built: 2000Community: Lighthouse PointSingle Family
Remarks: This bespoke crafted casually elegant furnished residence is in the exclusive gated Lighthouse Point waterfront enclave of just 16 custom residences at the southern tip of Longboat Key. Lighthouse Point is a peninsula nestled on a deep-water boat basin at the edge of the Intracoastal Waterway and New Pass. This residence has been completely remodeled within the past couple years, taken down to the studs to create the ideal coastal waterfront estate. Longfield Fitzgerald of Atlanta oversaw the interior design. The improvements included new impact glass windows and doors throughout and a new tile roof. The furnishings are chosen to make the space comfortable for both relaxing seaside living, as well as hosting family and guests. No detail has been overlooked. The first level includes an open floor plan with a living, family and dining room with a separate media room, and the fifth bedroom with double bunk beds for the little ones. Entering this stunning home, you are welcomed into a grand space, and beyond the beautiful kitchen with island seating, that includes the La Cornue French gas range as the focal point. The living and family rooms each have a gas fireplace. The main floor rooms overlook an expansive terrace and large heated pool with sun shelf chaises, back yard with plenty of space for games, private beach, and the Gulf of Mexico. Take the stately staircase or elevator to the second floor where the primary bedroom and three en-suite guest bedrooms are. The primary and two of the guest suites connect to a wide terrace overlooking the Gulf and Longboat Pass. Enjoy the Gulf’s vibrant sunset skies from the primary suite with spacious bedroom living space, meticulously appointed spa-like bath area, three walk-in closets and gas fireplace. There is a three-car side entry garage with room for storage. Down the street at the community dock is a new 16,000lb boat lift. Owners in the Lighthouse Point neighborhood enjoy their own tennis court plus the nearby gulf front beach, easy access to the Resort at the Longboat Key Club and the Links Golf Course and fitness center with famed St. Armand’s Circle shopping and dining district just over a mile away. Sarasota and its famed arts and entertainment is just 5 miles away. .
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