Longboat Key Condos For Sale - 225 condos

Remarks: Don’t miss this opportunity for a prime location in one of the most celebrated communities on Longboat Key. This first floor corner residence with walk-out back patio sits at the very end of the quiet 800 cluster, offering maximum privacy and 1570 square feet of effortless indoor-outdoor living. A favorite feature is the screened lanai that opens out to an extended west-facing patio. Perfect for easy mornings and catching brilliant sunsets. Step out to landscaped grounds and a direct path to deeded beach access across the road. The condo's open layout features a spacious kitchen, living and dining space, a primary bedroom with dual vanity bath, walk-in closets and nice little office nook overlooking the patio. Full sized laundry, covered under unit parking and a private storage closet add convenience. Offered fully furnished with a brand new high efficiency AC, this property is poised and ready to be a low maintenance island escape, year round residence or a smart rental, allowing 12 monthly rentals each year. Bayport is well known for it's timeless architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated and cooled Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths among 27 acres of exquisitely landscaped tropical grounds. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The mid-key location puts you close to shopping, daily conveniences, Duarante Park, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise.

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

Listing Agent: Rosemarie Mckee (941-504-9396)

Remarks: BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!

Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)

Listing Agent: Andrey Markov (941-363-1043)

Remarks: Under contract-accepting backup offers. Water Clubs most exquisitely renovated residence just became available for the first time! Meticulously reimagined from the studs up, this “Beach Beauty” immerses you in the essence of the Gulf below, every detail from the Azure toned palette to the warm honey finishes evoke a serene coastal escape with walls of windows frame the sweeping vistas from Bay to Beach while expansive terraces flow seamlessly between indoor and outdoor living - perfect for elegant entertaining or peaceful solitude. This modified “Dover” renovated floor plan Is located in the highly desirable end “8” stack which has amazing full gulf and bay views, the advantage of the private wrap around terraces elevate you above the lush tropical canopy to be soothed by remarkable natural light and uninterrupted vistas. Rich wide plank wood flooring sets a warm sophisticated tone throughout this impeccably designed residence. Only the finest finishes were selected, with designer fixtures, custom details and elegant appointments. Bespoke lighting creates a captivating ambience while custom remote shades and luxurious sheer drapery blend harmoniously with the curated furnishings. Offered beautifully “turnkey furnished” every detail is already in place allowing you to begin enjoying this extraordinary coastal retreat from the moment you arrive! Flowing seamlessly from the great room the stunning open concept kitchen is designed for both gourmet cooking and gracious entertaining. At its heart, a chef inspired island invites friends and family to join in creating culinary creations, Wine enthusiasts will appreciate the custom Euro wine cave perfectly positioned to keep your favorite vintages at hand for impromptu gatherings or elegant dinners. The exceptional kitchen is appointed with premium Thermador built-in appliances, induction cooktop, creamy quartz countertops, custom cabinetry with convenient pantry pullouts, and thoughtful storage throughout. Serving as a true sanctuary, the primary suite exudes the ambience of an exclusive spa retreat with a beautifully appointed vestibule separating the walk-in closet from the private luxurious bathroom. The primary bath with walk-in shower flows into the elegant sophisticated “boudoir” appointed with bespoke fixtures, and luxurious bedding and linens. Step out to the private terrace where the sounds of the Gulf will lull you to sleep. The 2nd Guest ensuite has an amazing Bay view terrace to enjoy the twinkling lights across the Bay at night. The generous walk-in closet is stocked with exquisite bedding, and towels to make your guests feel pampered. The full bath includes a walk-in shower, quartz vanity, and elevated lighting. The 3rd bed/den is a great escape for the kids or a private yoga studio - it segues smartly with the 3rd bathroom right down the hall for convenience, decorated with the same style and quality of décor and finishes. The Water Club is known for its full 24 hour concierge service, resort style living, offering children’s pool, 3 spas, 4 har-tru tennis courts, a Mediterranean spa clubhouse with fitness center, steam and sauna, library, many social spaces and Water Club is “pet-friendly”. Every corner of this amazing property has been reimagined with the finest materials and thoughtful design - It’s truly an artistic creation you must see to appreciate. Call now for a private showing.

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

Listing Agent: Kathy Callahan (941-900-8088)

Remarks: Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.

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

Listing Agent: Kim Ogilvie (941-951-6660)

Remarks: Welcome to your waterfront retreat in the highly sought-after Fairway Bay community, where relaxed coastal living meets thoughtful design and modern comfort. This beautifully renovated 2-bedroom, 2-bath condominium offers nearly 1,200 square feet of light-filled interior space, along with sweeping views of Sarasota Bay and the downtown skyline that create a stunning and ever-changing backdrop throughout the day. Fully updated in 2020 and professionally curated by an interior designer, the residence showcases a refined yet inviting aesthetic. Inside, the open-concept layout is enhanced by warm, driftwood-inspired luxury vinyl plank flooring and an abundance of natural light. The living and dining areas flow effortlessly together, while expansive pocketing sliders open wide to a private balcony, creating a seamless indoor-outdoor experience ideal for both quiet mornings and evening entertaining. From this vantage point, you can take in tranquil water views, coastal breezes, and vibrant sunsets that define the Longboat Key lifestyle. The galley-style kitchen is both stylish and functional, featuring quartz countertops, crisp Ivory soft-close cabinetry, New AC 2025, New Water Heater 2025, New Washer and Dryer 2025, stainless steel appliances installed in 2020, and a peninsula with seating that invites casual dining and conversation. The design balances clean lines with timeless finishes, making it equally suited for everyday living and hosting guests. The spacious primary suite serves as a private sanctuary, offering generous proportions, beautiful bay views, and direct access to the peaceful ambiance of the home. The en-suite bath is thoughtfully appointed with dual vanities, elegant lighting, and a walk-in tiled shower, creating a spa-like atmosphere. The guest bedroom and accompanying bath are equally well-designed, providing comfort and privacy for visitors while maintaining the home’s cohesive style. Additional features include plantation shutters on all windows and sliders, a private exterior entrance that enhances both convenience and privacy, a welcoming balcony seating area, and professionally landscaped surroundings that add to the property’s curb appeal. Important updates such as a new air conditioning system and water heater provide peace of mind, making this a truly move-in-ready opportunity. Fairway Bay, located within the desirable Bay Isles community, offers a lifestyle rich in amenities and natural beauty. Residents enjoy gated entry with 24-hour guard service, beautifully maintained grounds, resort-style pools, a clubhouse, fitness center, and tennis courts. Scenic walking and biking paths wind along the bay, while a kayak and paddleboard launch provides easy access to the water for outdoor enthusiasts. Ownership also includes exclusive access to a private beach club on the Gulf of Mexico, offering the rare advantage of experiencing both serene bayfront living and pristine Gulf beaches. Ideally situated near the renowned The St. Regis Longboat Key Resort, this residence is just moments from exceptional dining, shopping, and leisure experiences, further enhancing its appeal as both a full-time residence and seasonal escape. This is more than just a condominium—it is an opportunity to embrace the relaxed elegance, natural beauty, and effortless lifestyle that make Longboat Key one of Florida’s most coveted coastal destinations.

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

Listing Agent: David Leventhal (941-518-7694)

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: We are offering an exceptional investment opportunity at Bayport Beach & Tennis Club. Unit 521 is PRICED BELOW a recent June 2026 independent appraisal and currently the lowest-priced residence in the Bayport Beach & Tennis Club complex, we feel this beautifully updated condominium represents one of the best values on Longboat Key for a primary residence, seasonal retreat, vacation home, or investment property. Features include impact-resistant windows and sliding glass doors, City-permitted interior remodeling, a newer air conditioning system, covered parking, private storage, and numerous thoughtful upgrades throughout. The recent June 2026 independent appraisal, City permit records, association budget, reserve information, and HOA documents are available electronically upon request. Discover the essence of coastal resort living within Bayport's beautifully landscaped 27-acre Gulf-to-Bay community featuring 1,200 feet of private deeded Gulf of Mexico beachfront, direct Sarasota Bay access with a fishing pier and kayak launch, mature tropical landscaping, scenic walking trails, and an outstanding collection of resort-style amenities. Residents enjoy a heated Junior Olympic lap pool, four Har-Tru tennis courts, fitness center, clubhouse, community room, kayak launch and storage, professional on-site management, and one of Longboat Key's most desirable waterfront lifestyles. Conveniently located just minutes from Publix, Ace Hardware, Pickle ball facilities, waterfront dining, boating, championship golf, St. Armands Circle, The Ringling Museum, dog parks, and the cultural attractions of downtown Sarasota, Bayport offers the perfect balance of island tranquility and everyday convenience. Whether you're searching for a full-time residence, seasonal getaway, vacation home, or long-term investment, this move-in-ready residence offers exceptional value in one of Florida's premier Gulf-to-Bay communities. Experience the relaxed elegance, natural beauty, and resort lifestyle that have made Bayport Beach & Tennis Club one of Longboat Key's most sought-after addresses. Come experience why so many residents say that living at Bayport isn't just owning a home—it's embracing a year-round island resort lifestyle that others only experience on vacation.

Listing is courtesy of: PERSONAL REALTY ADVISERS (727-317-7653)

Listing Agent: Rob Coscia (239-770-2683)

Remarks: Rare 2BR First-Floor Lockout Unit | Resort at Longboat Key Club Experience the perfect blend of luxury vacationing and rental income with this rare, first-floor lockout suite overlooking the resort pool and just steps from the beach. • Versatile Rental Options: Lockout design allows you to rent as a full 2-bedroom suite or a 1-bedroom unit to maximize revenue. • Prime Location: First-floor convenience with an oversized deck, steps away from the beach, pool bar, and restaurants. • World-Class Amenities: Access to 45 holes of golf, 21 tennis courts, 5 restaurants, a luxury spa, fitness center, and a bayside marina. Perfect for families seeking a premium getaway with built-in investment potential.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)

Listing Agent: Tom Cinquegrano (941-284-5049)

Remarks: Under contract-accepting backup offers. 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. Experience beachfront luxury in this spacious 3,800-square-foot 3-bedroom, 3.5-bath + den/office residence in the prestigious En Provence community on Longboat Key. A private elevator opens to a grand foyer with marble floors and tray ceilings. Expansive glass sliders in the living room frame stunning Gulf views and lead to an oversized terrace, perfect for seamless indoor-outdoor living. The expansive terrace is ideal for entertaining, featuring a built-in gas grill and outdoor cooking space overlooking the beach and lush grounds. The kitchen is both stylish and functional, featuring a center island, white cabinetry, and pristine white stone countertops. High-end appliances, including a natural gas cooktop, enhance the space, while a bold blue tile backsplash adds a striking contrast. The adjacent eat-in area, with Gulf views and a built-in desk, enhances both charm and practicality. The primary suite offers terrace access and a spa-like bath with a soaking tub, dual vanities, a makeup area, and a glass-enclosed shower. Two guest suites each include en-suite baths and scenic views. A large office provides flexibility and could easily convert into a fourth bedroom. Additional features include an in-residence laundry room and 2 car garage. Set on nearly six acres of pristine beachfront, En Provence blends elegance and convenience with a clubhouse, resort-style pool and spa, fitness center, and 24-hour guard gate. For those seeking additional amenities, optional membership to the nearby Longboat Key Club provides access to world-class golf, tennis, dining, a marina, and a spa.

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

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

Remarks: Under contract-accepting backup offers. Arrive by private elevator into this TURNKEY FURNISHED 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: Under contract-accepting backup offers. 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: Under contract-accepting backup offers. Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately.

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

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

Remarks: Under contract-accepting backup offers. Tucked within Winding Oaks, one of Longboat Key’s most sought-after villa communities, this 3BR/3BA residence offers the scale and comfort of a single-family home paired with the simplicity of maintenance-free living. From the paver drive and walkway to the stepped front entry, the residence creates an inviting first impression before opening into a home defined by volume, light and connection to the outdoors. Step inside and soaring ceilings immediately create a sense of openness, while high-set windows invite natural light to move throughout the living spaces. Tile flooring and soft neutral tones create a clean backdrop that complements the peaceful setting just beyond the glass. Renovated in November 2025, the kitchen has been thoughtfully opened and redesigned into a true centerpiece for gathering and everyday living. A substantial island with seating anchors the space, along with stone countertops, white cabinetry, stainless steel appliances, a range hood, wine refrigerator and tile backsplash. An abundance of windows and an adjoining sitting area create a bright, welcoming space whether hosting guests or enjoying a quiet morning. The dining area transitions naturally into the living room, where cathedral ceilings, a corner fireplace and sliding glass doors connect the interior to the outdoors. Beyond, an expansive screened deck overlooks the community lake and fountain, creating a peaceful setting with multiple areas for dining, relaxing or entertaining. Privacy walls on either side enhance the feeling of seclusion while keeping the water views front and center. The primary suite is spacious and calming, featuring vaulted ceilings, engineered wood floors, a wall of sliding glass doors opening to the deck and a large walk-in closet with extensive built-ins. Also renovated in November 2025, the primary bath offers dual vanities, a walk-in shower, dressing area and separate water closet. Guest accommodations are equally well planned. One bedroom includes an en suite bath and walk-in closet, while another is currently configured as an office space with sliding glass doors opening to a private patio. Updated baths throughout, an in-residence laundry room and a 2-car garage add convenience. Set within the Harbourside golf course community, Winding Oaks offers a serene environment with a gated entrance, community pool and spa, and access to the full range of Bay Isles amenities, including deeded beach access through the private Bay Isles Beach Club.

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

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

Remarks: Virtually Staged. On the 3rd floor of Building One, this 3-bedroom, 3.5-bath residence opens to one of Longboat Key's signature views: the fairways and lagoons of the golf course in the foreground and Sarasota Bay stretching to the horizon beyond. A semi-private elevator landing opens to 2,369 square feet centered on a great room, where floor-to-ceiling sliders frame the water and open to a wide covered terrace. The living room and owner's suite both capture the bay-and-golf view and open to this terrace, while a second terrace off the kitchen overlooks the treetops and serves the two guest bedrooms. The kitchen features a center island, double wall ovens, and a built-in refrigerator. The owner's suite includes a custom walk-in closet and a marble bath with glass shower, soaking tub, and dual vanities, and one guest bedroom is fitted with a built-in desk and shelving for an easy home office. Original and ready for your finishes, it is a rare chance to make a bayfront retreat your own. Two deeded parking spaces and a private storage unit complete the offering. Behind the gates of Bay Isles, Grand Bay offers two heated pools, Har-Tru tennis, a fitness center, clubhouse, on-site management, and 24-hour security. Owners also receive deeded access to the private Bay Isles Beach Club on the Gulf. St. Armands Circle, downtown Sarasota, Harbourside golf and marina, and the beaches of Lido and Siesta Key are all minutes away.

Listing is courtesy of: HOUSE MATCH (941-213-7028)

Listing Agent: Matt Bohanon (941-726-8750)

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: 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: Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!

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

Listing Agent: Dianne Anderson (941-350-3513)

Remarks: Exceptional opportunity to own a beautifully furnished waterfront residence in a gated, amenity-rich boating community. This one-bedroom unit features hurricane-impact sliding glass doors and windows, allowing abundant natural light while providing peace of mind. Enjoy waterfront living with access to a private beach located at 4415 Gulf of Mexico Drive, complete with gated parking, indoor facilities, and beachside amenities. Residents have access to an impressive array of community features, including four heated swimming pools, a spacious fitness center, pickleball courts, tennis courts, kayak and bicycle storage, and a vibrant boating community with first-come, first-served boat slips. Additional amenities include a banquet hall and numerous social and recreational opportunities. Whether you're seeking a full-time residence, seasonal retreat, or investment property, this waterfront gem offers the perfect combination of coastal lifestyle, convenience, and value.

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

Listing Agent: Malihe Karimi (941-376-5099)

Remarks: Welcome to Spanish Main Yacht Club, one of Longboat Key's most beloved waterfront communities, where 55-plus living unfolds at an easy, unhurried pace between the Gulf of Mexico and Sarasota Bay. Tucked along a quiet street lined with tidy single-story villas and swaying palms, this fully renovated two-bedroom retreat captures the old-Florida charm that makes this island enclave so special, paired with the fresh, move-in-ready updates. Behind the arched front entry and crisp white stucco exterior with its white tile roof, a bright open interior welcomes you, where neutral tile floors run throughout and natural light pours through plantation-shuttered windows. The renovated kitchen is the heart of the home, outfitted with white shaker cabinetry, quartz countertops, a waterfall-edged peninsula, a soft glass-tile backsplash, and crisp white appliances, all opening to a generous living and dining area finished with crown molding and an easy coastal feel. A versatile bonus room wrapped in windows, with a door to the back patio, makes a wonderful sunroom, reading retreat, or home office. Both bedrooms are comfortable and well-appointed, served by two beautifully updated bathrooms, one with a tub and shower framed in subway tile, the other a glass walk-in shower with a mosaic floor and designer fixtures. A covered carport with room for a golf cart, plus interior storage for kayaks and beach gear, adds everyday ease. Brick paver walkways and lush tropical landscaping wrap the home, and the concrete tile roof is just over five years young. Life at Spanish Main is built around the water and the warmth of neighbors. Residents enjoy a heated pool overlooking the basin, a clubhouse, shuffleboard courts, kayak storage and launch, and a deep-water marina with boat slips available for a monthly fee, offering quick access to Sarasota Bay and the Gulf beyond. Best of all is the community's private Gulf beach access, just a short stroll away, along with shaded benches lining the lagoon and a waterfront green where slow mornings and golden evenings by the water become a way of life. Beyond the community, the white sand of Longboat Key's Gulf beaches is moments away, with the boutiques and dining of St. Armands Circle, downtown Sarasota's culture, and the laid-back charm of Anna Maria Island all within easy reach. Come experience the rare blend of comfort, community, and coastal beauty that makes this villa a place to call home. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)

Listing Agent: Toni Zarghami (941-248-2147)