Longboat Key Homes For Sale & Real Estate - 364 homes

Remarks: Arrive by private elevator into this 2BR + den, 3.5BA residence offering 2,550 sq. ft. in Grand Bay. Wood floors run throughout the main living areas, leading to floor-to-ceiling sliders with views of the Harbourside Golf Course and Sarasota Bay. The covered terrace extends the living space and is well suited for enjoying daylight and coastal breezes. The living and dining areas are well proportioned for everyday living and entertaining, with a tray ceiling in the dining room. A den with custom built-ins is currently used as an office and sitting area and offers flexibility as a potential third bedroom. The kitchen features white cabinetry, stone countertops, tile backsplash and ample counter space, along with an eat-in area that opens to the outdoor living area. The primary suite enjoys floor-to-ceiling glass and a bath with a walk-in glass shower, soaking tub, distinctive tilework and separate water closets. The guest bedroom offers quiet community views. A powder bath and an in-residence laundry room add convenience. Grand Bay amenities include a staffed lobby, clubhouse, two pools and spas, fitness center with saunas and Har-Tru tennis courts. Bay Isles privileges include walking paths and membership to the private Bay Isles Beach Club with gated Gulf-front access on Longboat Key, parking, restrooms and shaded picnic areas. Optional membership to the Longboat Key Club provides access to championship golf courses, private beach club, marina, tennis facilities, fitness center, dining venues and a full-service spa.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Bruce Myer (941-376-5311)

Remarks: Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the residence includes a large walkout screened lanai where you can enjoy gentle Gulf breezes and spectacular sunsets over the tranquil waters of the Gulf of Mexico. The thoughtfully designed layout provides abundant storage throughout, including generous closets in both bedrooms as well as a dedicated owner’s closet. Just steps from the unit, the pristine beach is a renowned nesting ground for sea turtles, offering the unique opportunity to watch dolphins and manatees pass by while relaxing on one of Florida’s most beautiful beaches. Cedars West residents enjoy a wide range of resort-style amenities, including a large heated and cooled swimming pool, two tennis courts, BBQ grilling areas, and convenient kayak and bike racks. Owners also have the option to generate rental income by taking advantage of Cedars West’s rare two-week minimum rental policy on Longboat Key. Don’t miss this incredible opportunity to experience the ultimate beachfront lifestyle.

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: John Milkovich (727-518-5058)

Remarks: Under contract-accepting backup offers. Welcome to this rarely available corner penthouse with its stunning bayfront views artfully framed by the freshly landscaped tropical oasis surrounding the resort-style pool. Boasting nearly 2600 square feet of interior space on two levels, this serene sanctuary offers three terraces plus 3 bedrooms and 3.5 baths (3045 square feet in total). A private courtyard sets the stage for a gracious residence with a warm European feel that lives like a single family home. Relaxed open spaces beckon with soaring ceilings, extra windows in the kitchen and great room (available only in end units), and a gas fireplace. The kitchen features a morning room with built-in desk and an aquarium window over the sink. Sliding glass doors seamlessly connect indoor and outdoor spaces. Mahogany double doors open into the primary suite with its patio access overlooking the bay and lush landscaping, volume ceilings, acacia wood flooring, walk-in and built-in closets and recently renovated luxurious bath. An additional guest bedroom (currently used as a den) with ensuite bath, laundry room and powder room complete the first level. On the second level a spacious third bedroom, office with built-in desk, shelving and storage, and full bath provide additional accommodations for family and friends. The home offers impact windows, plus storm shutters on larger windows for added protection. Enjoy the resort style amenities of Tangerine Bay Club, including a lagoon pool with waterfalls, lap lane and spa, day dock, fishing, kayak launch, tennis and pickleball courts, fitness center, clubhouse, walking paths and tropical landscaping. An oversized garage provides ample space for sports equipment and storage. Owners may join the newly remodeled Bay Isles Beach Club providing access to the Gulf of Mexico for a modest annual fee. Located on Longboat's south end, this gated community is just minutes from the new St. Regis resort and St. Armand's Circle with its shops and fine dining. A short drive over the Ringling Bridge brings the vibrant culture and renowned arts of downtown Sarasota. Optional membership in the Longboat Key Club across the street from TBC offers 45 holes of award winning golf, fine dining and a marina. Come see why Tangerine Bay Club is one of Longboat's most sought after communities and why Forbes named Longboat Key one of the top 25 destinations in 2025.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Sherry Dominick (203-605-9582)

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—while still allowing a future owner to complete their personal renovation plans once the building’s elevator modernization is finished. The furniture rental will extend for up to one year, giving the buyer time to enjoy the residence while preparing for future customization or construction. 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.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and pristine beach access just moments away. Enjoy your private backyard dock and kayak launch or secure your boat on one of the deepwater slips on the open bay. Excellent fishing and bird watching await right outside your door in this remarkable natural habitat. The spacious home is anchored by a stunning great room with vaulted cedar ceilings and exposed beams. The home features a 40-by-9-foot sunroom with bar area and handcrafted art shelves, a dedicated library, an inviting family room and a separate private office with extensive built-in cabinetry, providing warmth and functionality. Extensive decking spans the front entry and wraps around an inner atrium courtyard for alfresco dining. An elevated cabana-style shaded area invites relaxation in sun and shade. The kitchen with center island is positioned for hosting memorable gatherings. The primary suite offers a full wall of windows overlooking the tranquil bayou, two walk-in closets and an additional wall of custom storage. The split floor plan provides a separate wing for guests, featuring two additional bedrooms and baths for convenient hosting. Each guest room offers private access to the outdoor decks and views of the tropical center atrium. Two garages accommodate up to four vehicles, boats, golf carts or paddleboards. Many of the furnishings are included. In Land’s End, an intimate gated community of just 12 residences, owners enjoy maintenance-free landscaping, a heated pool, tennis and pickleball courts, and convenient deepwater boat slips, all artfully tucked among the trees for privacy. From here, it is a short visit or golf cart ride to the captivating sandy Gulf beach or local favorites, including Shore Longboat Key, Mar Vista Dockside Restaurant and Whitney’s. The adjacent plaza also offers multiple popular waterfront cafes, boutique shops, Ventura’s restaurant, and 24/7 gym or Pilates studio. Enjoy mesmerizing sunsets on the Gulf or sunrises on the bay from this waterside community. This is a rare offering in today’s marketplace, capturing the allure of Old Florida living in one of the island’s treasured enclaves.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)

Listing Agent: Cindy Fischer (941-465-1124)

Remarks: One or more photo(s) has been virtually staged. Enjoy the Longboat Key lifestyle in this beautifully renovated, standalone, 3-bedroom 2-bath home at an exceptionally low price. This villa has it all - water and marina views, a bright, modern open kitchen, new appliances, and an indoor laundry room. It is now ready for you to move in. The roof, A/C, and windows were replaced in 2015 and new doors were installed in 2026. Spanish Main's deeded access to Longboat Key's uncrowded beach is across Gulf of Mexico Drive, and the deep-water marina and kayak launch near your front door offers boat slips as available at a very low annual price. The clubhouse is being renovated, and the nearby heated pool is now available. Spanish Main Yacht Club, an over 55 community, is conveniently located near several restaurants, a lovely park, Town tennis, pickle-ball, dog park, fitness activities, and St. Armands Circle shops and restaurants. Let me show you what this beautiful, unique community has to offer!

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Adrienne Scott (941-264-5266)

Remarks: Under contract-accepting backup offers. PRICE REDUCTION! Coastal elegance meets relaxed island living in this beautifully renovated and fully furnished Key West–style waterfront retreat on Longboat Key. Offering boating, beach, and three bedrooms and three full baths, this thoughtfully designed home also features a private guest/in-law suite complete with its own full bath and kitchenette—ideal for extended stays or visiting family and friends. Step outside to your own tropical oasis, where a heated in-ground pool and expansive paver lanai create the perfect setting for alfresco entertaining. The well-protected canal frontage includes a private dock with boat lift, water, and electric, providing effortless access to Sarasota Bay, the Intracoastal Waterway, and the Gulf. Boating enthusiasts will appreciate the direct, easy navigation, while beach lovers will enjoy the nearby neighborhood beach access just a short stroll away. Inside, the open great room floor plan showcases plank wood flooring, a cozy fireplace, and an expansive Florida room overlooking the water. The well-appointed kitchen features gas cooking and generous workspace—perfect for the home chef. The spacious main-level primary suite offers a walk-in closet and private en-suite bath, while a separate guest bedroom and adjacent full bath provide comfort and privacy. On the ground level, the fully appointed in-law / guest suite opens directly to the pool and lanai area and includes a full bath and new kitchenette. A versatile bonus space offers endless possibilities—game room, fitness studio, hobby space, or additional lounge area. Recent improvements include a new roof, Florida room addition with impact windows, Hardie board siding, in-law / guest suite kitchenette cabinets and appliances, and more. Lush tropical landscaping, raised planting beds, a kayak launch, paver drive and walkways, privacy fencing, and a welcoming front porch complete the exterior appeal. Located in the friendly Norton Street neighborhood, residents enjoy a voluntary social homeowners association with regular gatherings—one of the many reasons this is considered one of the island’s most desirable year-round communities. Waterfront luxury. Easy boating. Close to the beach. 601 Norton is your opportunity to embrace the very best of island living.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)

Listing Agent: Michael Seamon (941-586-1802)

Remarks: Welcome to Beaches of Longboat Key - Unit 807 From a morning stroll on the beach to twilight cocktails on your wrap around balcony watching the glittering lights of Sarasota over the bay, you will experience beauty all around. Longboat Key, a jewel in the crown of the Sarasota Coastline, has so much to share. This elegantly appointed home will not disappoint. Custom finishes are abundant throughout the 1,842 sq ft condominium, not to mention the breath-taking views from the over 300 sq ft wrap-around balcony. This gracious home offers generous living space, with sweeping views from every window. Upon entering 807, you are greeted to stunning engineered Brazilian Cherry Hardwood flooring that continues throughout the home. A Reme Halo Air Purification System keeps the air fresh and clean. All windows and sliders are Impact. Beautiful crown molding throughout. The custom kitchen created by Campbell’s Cabinetry, Quartzite countertops, SubZero 42” Side by Side Refrigerator Freezer, Wolf Steam Convection Oven, GE Monogram Induction Cooktop, Zephyr PISA range hood. Bosch Dishwasher, Blanco Silgranite Sink, Hansgrohe Faucet. Custom cabinetry can be found throughout this beautiful residence. Primary Bedroom Suite offers views, comfort and luxury. Two bedrooms, each with well-designed baths, custom touches are found everywhere. There is one assigned parking space assigned to the unit on the upper level, and there is ample parking on the lower level for your second vehicle. Beaches is a great community offering you every convenience: 24-hour Concierge, Heated pool & Spa, Fitness Room, Tennis Courts, Social Room, Catering Kitchen, direct Walkway access to the Beach and a Basement Storage area. This proactive community is hard at work completing several important and vital projects: Stack Pipelining throughout the building, Roof Replacement will take place later this year and Temporary Wind/Surge Barriers are being purchased to protect the main floor of the building. Morning, noon and night, there is always something wonderful to experience at Beaches on beautiful Longboat Key. Schedule you showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: David Stasney (941-705-8464)

Remarks: Phenomenal opportunity to purchase a newly renovated condo in the exclusive Sands Point community. Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, nestled inside the gates of the highly sought-after, Longboat Key Club. This stunning 1,941 sqft second floor residence underwent a complete transformation in 2022-2023, and the results are nothing short of spectacular. Step inside this bright second-floor residence and discover three bedrooms and two bathrooms designed with meticulous attention to detail. Classic plantation shutters grace each room, while new tile flooring flows seamlessly throughout. The primary bedroom features custom-organized closets, while the second guest room cleverly incorporates a Murphy bed—perfect for maximizing space without sacrificing style. This split bedroom concept allows for privacy for your family and friends. The third bedroom doubles as a versatile office, adapting effortlessly to your lifestyle needs. The kitchen will make any culinary enthusiast weak in the knees. High-end appliances including a Fisher and Paykel induction range, Kitchen Aid dishwasher, refrigerator, and bonus refrigerated drawers all shine in crisp white enamel against stunning Shaker cabinetry and gleaming quartz countertops. The expansive living room steals the show with a dramatic wall of windows, gorgeous built-in cabinetry, and a dazzling dining chandelier that ties everything together beautifully. Both bathrooms feature light, airy cabinetry with elegant tile work and convenient walk-in showers. Community amenities abound—enjoy the beach with private tiki's and lounge chairs, pool, spa, library, community room with full kitchen, marina access, kayak launch, and bicycle storage. Nearby attractions include Overlook Park and Mote marine for endless exploration opportunities. With in walking distance to well renowned St. Armand's Circle for shopping and dining experiences. The pristine white sandy beach and gentle Gulf waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.

Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)

Listing Agent: Diane Smith (941-313-4957)

Remarks: Ask an L-dock boater, they will tell you its the best dock in the marina. Slip is near the seawall with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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 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 at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 63 LOA, usable beam is 23 ft at the head of the slip.

Listing is courtesy of: LBRE LLC (941-383-8383)

Listing Agent: Jennifer Wilson (941-809-7592)

Remarks: Experience the Ultimate Gulf-Front Lifestyle at Seaplace Wake up to breathtaking, unobstructed views of the Gulf of Mexico in this beautifully updated 3-bedroom, 2-bath residence at Seaplace on Longboat Key. This rarely available floor plan offers expansive living spaces and multiple areas to relax and entertain while enjoying endless turquoise water views. The spacious wraparound balcony and screened lanai provide the perfect setting for morning coffee, outdoor dining, or simply taking in spectacular sunsets and coastal breezes. Floor-to-ceiling sliders invite natural light throughout, seamlessly blending indoor and outdoor living. Inside, the residence features a bright, coastal-inspired interior with updated flooring, custom built-ins, and a thoughtfully designed layout. The kitchen and living areas flow effortlessly, ideal for entertaining or relaxed everyday living. The primary suite offers a peaceful retreat with serene views and a beautifully updated bath, while additional bedrooms provide flexibility for guests or a home office. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beachfront and an impressive array of resort-style amenities across 42 acres of lush, manicured grounds, including: Two heated swimming pools and spas Har-Tru tennis courts Fitness center Walking trails Clubhouse with kitchen, library, and sauna Playground and grilling areas On-site management 24-hour staffed gatehouse Located in the heart of Longboat Key, you’re just minutes from dining, shopping, and the cultural attractions of Sarasota. A rare opportunity to own a true Gulf-front, move-in-ready residence—perfect for full-time living or a luxurious coastal retreat.

Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)

Listing Agent: Michael Renick Pllc (941-400-8735)

Remarks: Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)

Listing Agent: Robert Delaney (941-315-3185)

Remarks: Framed by sweeping vistas that span the manicured Harbourside golf course, Sarasota Bay, and the distant city skyline, this 3BR/3.5BA residence in Grand Bay offers an exceptional vantage point that captivates from the moment you arrive. Positioned on the fifth floor, the perspective is both expansive and elevated, showcasing breathtaking panoramic views while maintaining a strong visual connection to the surrounding landscape. The living room is thoughtfully designed to highlight this remarkable setting, with a full wall of sliding glass doors opening to a balcony that extends the entire length of the residence. From this elevated perch, corner walls of glass draw the eye outward, creating a dramatic focal point where golf course, bay, and skyline converge in one uninterrupted panorama. High ceilings with crown molding and tile flooring provide a clean, timeless foundation throughout the main living areas. The kitchen offers generous space and functionality, featuring stone countertops, under-cabinet lighting, a center island, stainless steel appliances, a tray ceiling, and an adjacent dining area. Well laid out and highly functional, it also presents an excellent opportunity to personalize finishes and reflect your own design vision. A versatile bonus room with an enclosure feature adds flexibility, ideal for a private office, media room, or additional guest accommodations. The primary suite serves as a comfortable retreat, complete with direct terrace access and serene sunrise views over Sarasota Bay. The spacious bath includes dual vanities, a soaking tub, glass-enclosed shower, and a separate water closet. Additional conveniences include an in-residence laundry room and under-building parking. Residents of Grand Bay enjoy a refined, amenity-rich lifestyle, with access to a clubhouse, two pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Ownership also includes the privileges of Bay Isles, featuring gated entry, scenic walking paths, and membership to the private Bay Isles Beach Club. Large dogs are welcome.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Bruce Myer (941-376-5311)

Remarks: Under contract-accepting backup offers. It has been 20 years since a penthouse came to market at Regent Place on Longboat Key. Can you imagine the breathtaking views this elusive residence offers, spectacular sunsets over the Gulf and the twinkling lights of downtown Sarasota’s skyline? This extraordinary penthouse has been completely reimagined with coastal sophistication, featuring refined details meant to be experienced, not just seen. Designed by Anne Folsom Smith Interior Design and expertly completed by Ocean Builders, the renovation is timeless in style and function. Offering over 3,100 furnished square feet, the residence showcases 12-foot ceilings, electric storm shutters, private elevator access, a personal two-car garage and two expansive covered balconies, ideal for enjoying panoramic views in every direction. Every room reflects a custom, thoughtfully curated design, seamlessly blending luxury and livability. Highlights include a Crestron smart home system, Mr. Steam shower, Fisher & Paykel, Sub-Zero and Wolf appliances, Neff cabinetry, Hansgrohe fixtures, electric shades, and custom built-ins that beautifully define each space while maintaining an effortless flow throughout the home. This is a residence that must be experienced in person. Behind the gates of the Longboat Key Club, Regent Place is among the island’s exclusive luxury communities, with just 36 residences, ensuring exceptional privacy and premier amenities including a heated beachfront pool and spa, resident clubhouse and fitness center, on-site management and 24/7 security, over 500 feet of private beach frontage and in a pet-friendly community. Enjoy an unparalleled resort lifestyle with golf, tennis, spa services, fine dining and boating just outside your door. Moments away, St. Armands Circle and downtown Sarasota provide world-class shopping, dining and cultural experiences. This is a once-in-a-generation opportunity to own a spectacular penthouse residence. Schedule your private showing today.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Jo Rutstein (941-587-9156)

Remarks: Welcome to Sandpipers, a boutique Gulf-front condominium community on the desirable north end of Longboat Key. This well-maintained second-floor residence offers 2 bedrooms, 2 bathrooms, and 1,786 square feet of relaxed coastal living. The home has been meticulously cared for with classic finishes and a show-stopping view. Step onto the private, screened lanai and take in soothing Gulf breezes, the sound of the waves, and spectacular sunsets over the Gulf of Mexico. The expansive lanai creates an inviting indoor-outdoor living space, perfect for morning coffee or evening relaxation. Residents of the 10-unit Sandpipers community enjoy private beach access and a community pool. The residence is offered furnished, making an easy transition into island living. Conveniently located close to St. Armands Circle, downtown Sarasota, and the coastal charm of Anna Maria Island. This is a rare opportunity to own a spacious and thoughtfully laid-out Gulf-front condo in one of Longboat Key’s most desirable boutique communities. Schedule your private showing today.

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: April Green (941-773-1680)

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)

Remarks: Live the boater’s dream on exclusive North Longboat Key. This spectacular, newly built, coastal contemporary waterfront home provides easy access to the tranquil Intercoastal Waterway, sparkling Sarasota Bay and majestic Gulf of Mexico. Located on a three-quarter acre lot with 133 feet of frontage on a 125-foot-wide canal, this 4,210-SF home features an open floorplan with light-color finishes, quartz hard surfaces and wood-look tile flooring. The large kitchen includes a Sub-Zero glass door refrigerator and Thermador appliances. There is an additional full outdoor kitchen with a gas grill, vent hood and U-Line refrigeration. A spacious first-floor office/den overlooks the waterway. There are 5 ample en-suite bedrooms, 2 half-baths. Relax in the second-floor master suite Jacuzzi tub or take the spiral staircase up to the third-floor observation deck to relish the serene views. The large, heated pool includes a Jacuzzi with a sun shelf for year-round enjoyment. During the cooler months, enjoy a relaxing evening in the great room in front of the fireplace or outdoors near a mesmerizing fire pit. Additional luxury amenities include a 60-foot composite deck with a 10x10 sitting area, fish station, water spigots on dock, bumpers, cleats and underwater lights. Water safety features include a new 133-foot seawall raised 13 and vinyl panel fronts on the 125-foot-wide canal. Make use of the two boat lifts – one 20,000-lb. and one 15,000-lb. and an additional Jet Ski spinner lift to delight in a fun-filled day on the water. This stunning home is ideally located near St. Armands Circle, pristine beaches, fine dining and specialty boutique shops. With professionally landscaped grounds, electric drive security gate and easy access to the bay, this luxurious property is perfect for discerning devotees of the boating lifestyle. This property, along with the beachfront property across the street can be sold together.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Steve Walter (941-809-0907)

Remarks: TURNKEY Furnished Portobello condo with Deeded Beach Access! TWO Balconies with Sunsets AND Sunrises included! Enjoy Beach and Bayou water access! Rarely available end unit with two balconies and lots of privacy and natural lighting. The front open balcony has unobstructed Gulf views whilst the rear balcony is glassed in with sliders/screens and faces the Bayou. This 4th Floor condo has elevator access, 1 owners storage locker, ample in unit storage and 1 assigned parking space. Condo fee includes Water, Sewer, Trash, Cable/Internet, Pest Control, on site Maintenance and Exterior Insurance. Well established social community with Community Pool, Clubhouse, Tennis Courts, Kayak storage/launch, Fishing Pier, BBQ area and ELEVATED mature landscaping. This spacious floorplan is one of the larger floorpans in the community providing you with list and bright spaces, tons of closet space and even a bonus study/den area to use as you please! Stacked Washer/Dryer located near the hallway 2nd Bathroom which has been renovated. Beautifully upgraded Kitchen with high quality cabinetry and 4 storage closets for all your pantry, cleaning and large cooking items. The Primary Bedroom has the most wonderful private bayou water views! Attached en suite full bathroom with lots of counter space. Secondary bedroom has its own separate balcony entrance. This community is located a short drive away from Publix, CVS, banks, Post office, nail salons and Golfing! New development nearby is bringing more shopping and dining! Don't miss this opportunity to own in the sough after Portobello community!

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Monica Desomma (202-427-4328)

Remarks: Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Sean Clark (941-312-1146)

Remarks: Under contract-accepting backup offers. ALERT: MARKET SHOCKER! STOP THE SCROLL! This Is The Lowest-Priced Villa in Prestigious Windward Bay—Period. Looking for a Beach/Bay Getaway Villa? LOCATION! LOCATION! LOCATION! This cozy End Unit Beach/Bay 2-bedroom/2-bath Sunny Villa boasts 1084 square feet of Longboat Key Florida Fun! Single story living with a convenient covered carport only a few steps away from your front door. Villa 15 is located directly across the street from the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded soft sandy beaches that attract visitors from all over the world. (Take joy with 3 beach access points, one private deeded) Enjoy walks along the shore, kayaking on the bay or read a book, unwind and soak up the sun on your own private patio while taking in the beauty of this incredible location. The patio is an ideal spot for morning coffee, watching a game of shuffleboard, hosting friends for sunset libations, evening grilling, or simply relaxing in solitude. Your beach/bay lifestyle possibilities are endless. Worry free living with recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). As an added bonus with the sale of this Villa, the longtime owner since 1976, former Canadian Navy-Man, and a wonderful Nonagenarian, will be leaving most of his nautical treasures gathered from lands around the world for you to enjoy. Set like a jewel on the barrier island of Longboat Key, the community of Windward Bay is a magical wildlife haven nestled mid-island, flourishing on 26 acres and graced with 1/2 a mile of waterfront trails to relish. A low-density residence and a nature lover’s delight to gaze both frolicking dolphins and manatees as they play. Bird enthusiasts jubilate with their front-row seat of the magnificent Florida birds that call Windward Bay their home. Witness the vibrant plumage and graceful flights of these majestic creatures as they effortlessly navigate the glorious skies above. Windward Bay offers numerous amenities that make it an exceptional value including: 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee, barbecue grills throughout, fishing piers, 2 fish cleaning stations, kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits throughout the property. Conveniently accessible to Downtown Sarasota, St. Armands Circle, Anna Maria Island, Historic Cortez Fishing Village, Championship Golf Courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Welcome home to “Pet Friendly” Windward Bay, where TWO pets are allowed. Windward Bay is a financially healthy Condo Association with a proactive Board. Monthly Condos Fees in 2025 were actually reduced and since 2024 have only increased by $2 a month. The Milestone Inspection and Capital Reserve Study are complete. THIS VILLA HAS NO PREVIOUS ASSESSMENT ADDED TO MONTHLY HOA FEES! This wonderful villa exemplifies “Florida Gulf to Bay Living” at its finest. Perfect for couples or individuals seeking paradise! Schedule your private tour today and make these experiences a reality.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Debby Mccaig (941-544-1713)