Homes For Sale in Longboat Key 34228 - 412 homes

Remarks: “PRICED BELOW MARKET VALUE NOW REDUCED TO $475,000” Fully renovated 2 Bedroom 2 Bath Whitney Beach Bay Side FIRST FLOOR condo ready for occupancy. It has undergone FEMA approved storm mitigation & has had a full rebuild & inspections. All new handsome Luxury Vinyl Plank flooring throughout plus tile in the primary bedroom’s stunning en suite with shower & 2nd bathroom with tub. Large, impact resistant sliders in the lanai area overlooking the canal waterfront & living room area & front door have been installed. A brand new kitchen was installed with quartz counters, custom cabinetry, stainless steel refrigerator & stove & new overhead lighting fixtures in every room. This like new & totally improved condo offers almost 1,500 square feet of interior living space plus a storage room at the entry which has a new stackable washer & dryer. Whitney Beach Bay Side offers two heated pools, kayak launch & storage, boat slips, fishing docks & a charming boathouse overlooking serene Bishop’s Bayou which leads to Sarasota Bay. This rental friendly community allows minimum of one month rentals, six times a year. It is also pet friendly allowing large dogs one of very few on Longboat Key. On the deeded beach access/Gulf of Mexico side, there is the Whitney Beach Conservancy land owned by the condo association for the use of owners, tenants & guests. Tennis & pickleball courts, a barbecue & picnic area & tike huts lead to the gorgeous sandy beach where you will enjoy swimming, sunning, shell collecting , and gatherings with neighbors while watching the most stunning sunsets you will ever see!

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

Listing Agent: Maruta Miluns (941-374-9702)

Remarks: Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost 200 feet of pristine waterfront, with breathtaking views of the downtown Sarasota skyline and a protected deep-water yacht slip. Deeded access to a private Gulf of Mexico beach club enhances the ultimate coastal lifestyle. Inside, the home features an exceptional floor plan with four luxurious bedroom suites and numerous entertainment spaces, including a formal living room, dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. Expansive waterfront terraces, a redesigned viewing porch, and his-and-her offices add to the home's functional elegance. Every detail has been executed to perfection, from the impeccable millwork to the finest finishes throughout. With magical views from every room, this estate embodies class, comfort, and privacy in one of Sarasota's most coveted locations. Experience refined waterfront living at its finest.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Jonathan Fox, Pa (941-544-6649)

Remarks: Welcome to 6851 Longboat Drive South, a completely renovated waterfront retreat offering the best of Longboat Key living. This exceptional residence features four bedrooms and four baths, including a private guest suite above the garage, and office/gym space, making it ideal for hosting family and friends in comfort and style. Designed with coastal elegance in mind, the home showcases light-filled living spaces, a modern open layout and high-quality finishes throughout. The seamless indoor-outdoor flow leads to tranquil waterfront views, ideal for entertaining or unwinding after a day on the water. Boaters will appreciate the private dock, providing direct access to the bay and making it easy to enjoy fishing, cruising or sunset rides right from your backyard. Every detail has been thoughtfully updated, offering peace of mind and turnkey convenience. Just minutes from the Gulf beaches, St. Armands Circle and Longboat Key Club, this property delivers a rare opportunity to own a move-in-ready waterfront home in one of Florida’s sought-after island communities.

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

Listing Agent: Barbara Szumski (941-232-8776)

Remarks: The most convenient dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Nicely manicured lawn fronts the area at the slip. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much as a resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!

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

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

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)

Remarks: Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the view of the Gulf of Mexico and Sunsets from your balcony. To see this property is to fall in love with easy living! You need to visit this unit to get a sense of the remarkable views , especially the amount of light that permeates the entire interior. Beachplace is a perfect get away on the south end of Longboat Key, and comprise many amenities. Pickle Ball, Tennis, two exercise facilities, Olympic pool, with designated lap lanes, over size hot tub , covered baby pool . Electric car chargers, gas grill, two types of workout facilities on almost 31 acres of lush landscaped grounds. Please visit to see why this building and unit are the best of BEACHPLACE!

Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)

Listing Agent: James Weingart (440-623-9068)

Remarks: This junior suite, located in Building 4, offers spectacular northwest-facing views of the Gulf, providing owners with breathtaking sunsets and expansive water vistas. The suite has undergone a complete renovation, ensuring a modern and refreshed living space for its occupants. Currently, the unit is integrated into the hotel program, providing potential owners with a streamlined rental management option. This sought -after hotel condominium enjoys strong rental activity and a proven history of guest demand, making it an attractive opportunity for investors and seasonal owners alike. Building 4 itself boasts an advantageous position on the northernmost stretch of the beach, promising a sense of quietude and enhanced privacy away from the main pool areas. Ownership of this suite grants exclusive access to the prestigious member-only Longboat Key Club. This membership unlocks a wealth of amenities designed to elevate the lifestyle experience, even during owner-occupied periods. Culinary delights await at five exclusive restaurants, offering a diverse array of fine dining options. Golf enthusiasts can indulge in 45 holes of championship golf, while tennis players can hone their skills at the award-winning Tennis Gardens. For relaxation and rejuvenation, a state-of-the-art spa and wellness center is available. The pristine white sandy beach is complemented by umbrella service and attentive waitstaff, ensuring a luxurious beach day. Furthermore, a full-service marina caters to boating enthusiasts.

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

Listing Agent: Jackie Kleppinger (941-320-0049)

Remarks: Exceptional opportunity to own a fully renovated, direct waterfront condo with a private dock on coveted Longboat Key. Perfectly positioned along a quiet canal with direct access to the Intracoastal Waterway, this turnkey coastal retreat offers 2 bedrooms, 2 bathrooms, covered parking, additional guest parking, and 1,215 sq ft of beautifully updated living space designed for effortless island living. Wake up to tranquil water views, enjoy morning coffee with coastal breezes, and keep your boat just steps from your door while enjoying the laid-back luxury that defines Longboat Key living. Completely renovated with all improvements fully permitted, this residence offers both style and peace of mind. Recent upgrades include a stunning new kitchen with brand-new appliances, new A/C system, new plumbing, new water heater, upgraded electrical panel, and all new windows. The building also features a durable metal roof installed in 2016, providing added value and potential insurance benefits for years to come. Inside, the bright and inviting interior blends modern coastal finishes with comfortable waterfront living, creating the perfect space for both everyday enjoyment and entertaining guests after a day on the water or beach. For buyers seeking both lifestyle and income potential, the property offers strong rental appeal with estimated seasonal rental potential of approximately $5,000 per month and off-season rental potential of approximately $3,500 per month, making it an attractive opportunity for part-time residents, second-home buyers, or investors looking to offset ownership costs. Ideally located just moments from the Gulf beaches, waterfront dining, boutique shopping, golf, and the cultural attractions of Sarasota, the property is also near Joan M. Durante Community Park, offering scenic walking trails, lush mangroves, and breathtaking Sarasota Bay views.

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

Listing Agent: Connor Meckley (941-279-0013)

Remarks: Breathtakingly gorgeous PENTHOUSE level condominium recently and meticulously redesigned to a clean-line ultra-luxury residence with advanced ultra smart-home technology managing the entire home. This rarely available opportunity offers a refined coastal lifestyle with the highest quality for the discerning buyer. The 4400-square foot custom residence features a dramatic private 5300-square foot wraparound terrace with outdoor kitchen and panoramic 270-degree sunrise-to-sunset views of the area including Sarasota Bay, the golf course, Sarasota city skyline, marina, Gulf of Mexico and beach area of Longboat Key. At an understated tasteful level of luxury living, the thoughtfully designed space now offers 3 ensuite bedrooms, an entertainment room, a den or office, living room, dining area, and a large functional kitchen featuring Cucine Ricci cabinetry, Dornbracht fixtures, high-end appliances, and a discreet area containing the butler's pantry, dry bar, and extensive storage. A premium Lutron smart-home system manages lighting, air conditioning, doors, window treatments, plumbing fixtures and electronics enhancing home convenience and elegance. The impressive primary bedroom suite is complete with stunning views, a fabulous dressing room with multiple built-ins, expansive personalized and automated bathroom with heated tile floors & towel racks, and sleek clean-finish tile & minimalist easy-cleaning cabinetry. Each private and spacious guest suite is thoughtfully planned with a complete built-in beverage center, bathrooms with heated floors and private balcony. As an extra bonus this sophisticated penthouse is sold fully furnished with high-end custom furniture tailored to the design. Words cannot describe this extraordinary residence purposefully created with no expense spared and where nothing has been overlooked. It must be experienced to be appreciated. Also included are two deeded parking spaces with Tesla charging station and air-conditioned storage unit. Grand Bay is among Longboat Key’s premier gated communities, offering resort-style amenities including two heated pools, Har-Tru tennis courts, a well-equipped fitness center, clubhouse, and social activities. Residents benefit from on-site management and 24-hour security. Ownership includes deeded access to the private Bay Isles Beach Club, featuring a Gulffront 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. Appraisal available.

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

Listing Agent: Carolyn Donnelly, Pa (941-350-9900)

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)

Remarks: Under contract-accepting backup offers. Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony. The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street. Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports. Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value.

Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)

Listing Agent: Shauna Ruby (941-544-2070)

Remarks: Welcome to 6700 Gulf of Mexico Drive #117, a beautifully reimagined end-unit 2-bedroom, 2 full bath residence in the sought-after Whitney Beach community on Longboat Key. Taken down to the studs and completely renovated, this waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou, abundant natural light, and exceptional privacy. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout, and a bright, open layout immediately draws your eye to the water. As an end unit, additional windows enhance the airy feel, while hurricane-impact windows and sliding doors frame tranquil bayou views. From the main living space—and even from the primary bedroom upon waking—you’ll enjoy peaceful scenes of dolphins, manatees, and glowing sunsets reflecting across the water. The fully redesigned kitchen is both stylish and functional, featuring granite countertops, soft-close cabinetry, custom glass-front accents, classic subway tile backsplash, designer pendant lighting, peninsula seating for four, and a full suite of GE stainless steel appliances—all positioned to capture the water views. Both bathrooms have been completely renovated with glass walk-in showers, elegant tilework, and quartz-topped vanities, offering a clean, modern aesthetic. A new Whirlpool stackable washer and dryer adds everyday convenience. Whitney Beach is a unique beach-to-bay community with deeded private access to the Gulf just across the street. Residents enjoy resort-style amenities including pools, tennis courts, shuffleboard, barbecue areas, kayak storage and launch, walking paths, and a tranquil bayfront pavilion. Boat slips are available when offered, and the community pier provides a charming setting for fishing or relaxing by the water. Ideally located on the north end of Longboat Key, this residence offers easy access to Anna Maria Island, as well as the dining, shopping, and cultural attractions of Sarasota. Whether as a full-time home, seasonal retreat, or investment, this is an exceptional opportunity to enjoy the best of bay-to-beach living. Professional photos coming soon.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Kelly Sallee (941-914-0400)

Remarks: Welcome to this beautifully appointed ground floor residence that combines modern elegance with functional design. Newly remodeled in 2025, this residence features high-end finishes and modern amenities, making it an ideal retreat for those seeking luxury in a serene environment. Upon entering, you are greeted by a bright and spacious interior filled with natural light, thanks to strategically placed additional windows featured in corner/end units of this community. The subtle elegance of the interior is complemented by sleek flooring that enhances the flow from room to room. The kitchen is a true highlight, featuring quality cabinetry, elegant quartz counters, and modern stainless-steel appliances, which allow a harmonious flow, delivering both functionality and sophistication. The open-concept layout continues through the dining and living areas, combining a blend of textures and stylish finishes to cohesively create an environment of relaxed elegance. An abundance of natural light floods this space through large retractable sliding glass doors, which provide the option of extending the outdoors in. A private outdoor patio showcases a beautiful backdrop of lush tropical landscaping, adding to the property’s overall appeal. The bedrooms within the property are thoughtfully designed, each offering generous space and natural light. The primary suite offers a restful retreat, complete with an ensuite bathroom featuring modern fixtures and thoughtful design, ensuring comfort and privacy. This property will continue to amaze, as beauty extends beyond its walls into an amenity-rich community of 27 acres of picturesque tropical landscaping. This gulf-to-bay community offers an active island lifestyle with 4 Har-Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court, and amazing nature trails. A distinct advantage and unique selling point of this property is its proximity to a private, deeded beach. This property offers future owners not just exclusive beach access, but a revitalizing retreat amidst the hustle and bustle of life—truly a valuable benefit that amplifies the charm of this residence. Close to local amenities yet precisely positioned to offer privacy and quietude, this property represents an excellent opportunity for discerning buyers. Experience the best of coastal living in this beautiful home, where modern comfort meets natural beauty. Welcome home!

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Antonietta Car (813-684-9500)

Remarks: BACK ON THE MARKET with a New Price and Turn Key! Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, and nestled inside the gates of the Longboat Key Club. This gorgeous 1492 sq. ft. water front residence underwent a total transformation in 2023, and the results are nothing short of spectacular. Step inside this bright second floor residence and discover a two bedroom and two baths, with a view that feels serene, luxurious, and unmistakably coastal. This condo comes with a view of the private marina tucked away in a quiet cove, where you can enjoy watching the dolphins at play. Towering palm trees frame the scene beautifully, with the curved waterfront drive adds a resort-style elegance to this one-of-a-kind property. This kitchen has a bright, modern, upscale feel with a clean coastal-inspired design. White shake-style cabinetry with sleek brushed nickel handles, extending all the way to the ceiling for extra storage. Exotic granite counters, matched with a sleek white Carrara marble back splash. Stainless steel appliances, and a deep undermount sink with a tall industrial-style spring faucet. The expansive great room steals the show, with a dramatic wall of windows, open concept and LVP flooring thru out. Both bathrooms feature quartz counter tops, tiled floors and walk in showers. HVAC 2020. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room with kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. With in walking distance to well renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise 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: Direct beachfront living! This beautifully updated 2-bedroom, 2-bath residence offers unobstructed Gulf of Mexico views and front-row access to a slice of Longboat Key’s most quiet and uncrowded shoreline. Available fully furnished and turnkey, this condo is ready for immediate enjoyment as a primary residence, seasonal escape, or investment property. The spacious open layout connects the kitchen, dining, and living areas, creating a bright and functional space designed to maximize natural light and water views. The private balcony is the perfect place to spot dolphins, manatees and other wildlife while enjoying morning coffee or evening sunsets. With only 42 residences, Tiffany Plaza offers a more private and welcoming atmosphere than larger condominium communities, with an active clubhouse and strong sense of community among owners. Residents also enjoy close proximity to Bayfront Park, featuring dog parks, tennis, pickleball, kayak facilities, fitness classes, and beautiful bay front walking paths.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Daniel Goldman (516-761-1911)

Remarks: Under contract-accepting backup offers. IN THE COVETED "B" BUILDING, A STRATEGIC PRICE REFINEMENT NOW POSITIONS THIS EXCEPTIONAL RESIDENCE AS THE MOST COMPELLING OFFERING AT WINDWARD BAY! A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!

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

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

Remarks: Wake up to calm canal views, step outside to the water, and enjoy the effortless lifestyle that makes Longboat Key one of Florida’s most desirable coastal destinations. This beautifully updated 2-bedroom, 2-bath condo offers 1,215 sq ft of thoughtfully designed living space, along with a carport and two dedicated parking spaces—a rare convenience for island living. Ideally positioned on a quiet canal with direct access to the Intracoastal Waterway, the property is perfect for boating, relaxing, and enjoying the best of waterfront living. Inside, the residence has been completely transformed into a clean, coastal, move-in-ready retreat, ideal for both personal use and hosting guests. The renovation was fully permitted and completed with a focus on long-term value and peace of mind. Major improvements include a brand-new kitchen with updated appliances, new A/C, full plumbing repipe with new water and sanitary lines, new water heater, upgraded electrical panel, and all new windows. The building also features a metal roof (2016), offering durability, insurance advantages, and low-maintenance ownership. Beyond the lifestyle, the property also offers proven income potential, generating approximately $5,000+ per month in season and $3,500+ per month in the off-season, making it an ideal blend of personal enjoyment and investment performance. Located just minutes from Gulf beaches, dining, and everyday conveniences, and near Durante Park, known for its scenic walking trails, gardens, and bayfront sunset views. Rare Opportunity: The adjacent unit is also available, presenting the unique chance to own the entire building as a waterfront duplex—ideal for a private compound, multi-generational living, or maximizing rental income. Whether you're seeking a primary residence, seasonal escape, or income-producing investment, this property offers a rare combination of location, condition, lifestyle, and investment. Schedule your private showing and experience Longboat Key waterfront living for yourself.

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

Listing Agent: Connor Meckley (941-279-0013)

Remarks: BACK on the market after beautiful renovations!! Unit is impeccably maintained. It has a new air conditioner, roof and upgraded insulation. It is being offered below appraised value! Sands Point is the most remarkable and unique complex on Longboat Key. Built in 1966, the building is a magnificent example of mid-century modern architecture. The complex faces directly onto New Pass, and the outdoor pool and patio have both privacy and spectacular views. The center of the unit is a large great room that features a wall of windows and a view of lush Florida greenery, the boat dock and the navigable inlet which leads to the Gulf of Mexico. Kitchen and bathrooms are renovated. Furniture and furnishings are included in the sale. Windows have been upgraded to the highest level available. Each unit comes with a small storage locker near the boat docks and covered parking. There are boat docks on the premises, approximately 30 ft., that can be rented depending on availability. Management has updated status and detailed information. Sands Point is located adjacent to The Resort at Longboat Key Club with its amenities of golf, health spa, lodging and a restaurant. Nearby is the famous St. Armand's Circle that offers elegant or casual dining and entertainment. Seasonal rental is a huge draw for this property. It may be rented once a year for a minimum of one month.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Carolyn Clark, Pa (941-685-6131)

Remarks: Located in the Grand Bay community on Longboat Key, this spacious 3BR residence offers stunning views and desirable extras, including 2 conveniently located parking spaces. The pet friendly community allows up to 2 large dogs. The home features luxury vinyl flooring and neutral tones throughout, with floor-to-ceiling windows and plantation shutters that let in natural light. Elevated ceilings and accent lighting create an open, airy feel, while you enjoy views of Harbourside Golf Course, Sarasota Bay, and the downtown skyline from the expansive wraparound terrace that is perfect for entertaining or relaxing. The updated kitchen includes white cabinetry, Corian countertops, tile backsplash, stainless steel appliances, including a Sub-Zero refrigerator, and a central island. The living room/dining room offers ample space for a formal dining room table and large seating area. The primary suite is a private retreat, with access to the terrace and newly enhanced sightlines from the bedroom showcasing beautiful views of the Longboat Key Club golf course and Sarasota Bay. The primary bath features dual vanities, a walk-in shower, and a spa tub. The large custom closet is thoughtfully designed for ample storage. A full-size laundry room adds convenience. Grand Bay offers resort-style amenities including 24-hour gated security, a clubhouse with a library and game room, fitness center, 2 Har-Tru tennis courts, 2 heated pools, and a spa. Residents also enjoy deeded beach access through the Bay Isles Beach Club, just a short bike ride away. This private beach offers a peaceful, uncrowded environment, with a beachside pavilion, restrooms, and showers. Additionally, for those seeking more exclusive amenities, the optional Longboat Key Club provides access to luxury services, including golf, fine dining, a full-service spa, and fitness facilities.

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

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

Remarks: Introducing a highly sought-after first-floor Junior Suite in Building 4, boasting stunning Gulf views and now available for purchase. This fully renovated unit is part of the hotel program, generating over $118K in gross income for 2025, with more than $79K already booked through April 2026, indicating the potential for even greater earnings this year. Enjoy an expanded deck alongside a covered terrace that offers direct beach access. Positioned at the northern end of the gulf side, Building 4 provides owners with a sense of privacy from pool activities while still being close to all amenities. As an owner, you gain access to the exclusive offerings of the 410-acre Longboat Key Club, including five fine dining options, 45 holes of championship golf, the award-winning Tennis Gardens, a spa and wellness center, a pristine white sand beach with umbrellas and waitstaff, and a full-service marina. The renovated rooms, main dining area, pool, and guest services enhance the experience at this award-winning property, recognized with accolades such as the AAA Four-Diamond Award and Condé Nast Travelers' Top Florida Resorts. Embrace the Longboat Life today!

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

Listing Agent: Ian Addy, Pa (941-961-8850)