Windstar Naples Real Estate - 4 Homes, 15 Condos For Sale

Rare waterfront estate on exclusive Southpointe Island at Windstar on Naples Bay. Tucked behind double gates within an intimate enclave of only ten estate residences, this exceptional property offers privacy, direct Gulf access, and an unparalleled Naples lifestyle just minutes from downtown and world-renowned beaches. Positioned on nearly half an acre, this home features a private 40-ft dock in the backyard with the option to purchase an additional 50-ft protected slip in Windstar’s private marina—an extraordinary offering seldom available in Naples Bay communities. Spanning over 6,100 sq ft of refined interior living space, this 5-bedroom + den, 4 full and 2 half bath residence showcases spectacular 20+ ft contoured ceilings, abundant natural light, and meticulous attention to detail throughout. The chef’s kitchen is designed for both function and style, featuring custom cabinetry imported from Japan, quartzite countertops, a gas cooktop island, premium appliances, and seamless flow to the expansive outdoor living areas. The luxurious owner’s suite offers tranquil water and preserve views, a private balcony, and a spa-inspired bath with jetted soaking tub and walk-in steam shower. An elevator provides convenient access to the second level. Impact-resistant WinDoor windows and doors and a newer roof provide peace of mind. Outdoor living is exceptional, with nearly 5,000 sq ft of covered and open-air space including multiple balconies, a custom saltwater pool and spa with cascading water features, summer kitchen, and spacious lanai—ideal for entertaining or quiet waterfront relaxation. Residents of Windstar on Naples Bay enjoy access to a full suite of private club amenities, including championship golf, tennis, an active clubhouse, private beach access via shuttle, and a full-service marina with harbormaster. Membership opportunities subject to club approval and availability. A rare opportunity to own an estate-level waterfront home combining boating, privacy, and proximity at an exceptional value on Naples Bay.

Welcome to 1530 Star Point Lane in the highly coveted enclave of Admirals Watch of Windstar on Naples Bay. Enter the lobby of this 4-unit boutique building to the elevator which opens directly into your sprawling 4 Bedroom/4.5 Bathroom 2-story penthouse home in over 5000 square feet of living space with gorgeous, expansive southwestern views of golf course, Naples Bay, Port Royal, Royal Harbor and endless sunsets. This exceptional unit comes with a deeded boat slip ideal for boat lovers. Elevator opens you directly into your unit with a dramatic entry foyer with a gorgeous staircase. Open-concept living space with lovely living and dining rooms. Spacious eat-in kitchen replete with white shaker cabinetry, granite countertops, stainless steel appliances and custom beams is truly an entertainer's dream. Breakfast area directly overlooking the bay. Comfortable media room plus a home office with custom built-ins both with dramatic views, powder room plus 2 gracious guest suites. Ascend via the stairs or elevator to your Master Suite Oasis featuring a large bedroom with a wall of glass opening out to balcony with the most glorious views, en-suite bath with walk-in shower, soaking tub, separate vanities and separate water closet. Large walk-in closet with custom built-ins. Additional guest suite currently set up as a sitting room would also make a fabulous dressing room with additional full bathroom creating a truly luxurious Master Floor Oasis. 3-car attached garage. Deeded boat slip #1 behind the building which can accommodate up to a 30 foot boat and is just a mere 7 minutes out to the Gulf of Mexico. Gorgeous resort-style pool. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with boat shuttle plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal, game room, 6 Har-Tru tennis courts, 3 bocce courts and a state of the art fitness center slated for late 2026 completion. Preferred location just a short drive via car, bike or golf cart to downtown's 5th Avenue known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports. This exceptional home is truly a rare find.

Welcome to 1520 Star Point Lane in the highly coveted enclave of Admirals Watch of Windstar on Naples Bay. Enter the lobby of this 4-unit boutique building into the elevator which opens directly into your truly exceptional unit boasting expansive panoramic 180 degree views of Naples Bay, Port Royal and Royal Harbor. This home has been thoughtfully redesigned and renovated in 2021 by premier local builder/contractor, BCB Homes. No expense spared with only the finest craftsmanship and building materials, this home has been totally transformed into a modern sanctuary ideal for today's Naples lifestyle. Fabulous open-concept living area takes full advantage of the stunning bay views. A true chef's eat-in kitchen replete with Sub-Zero refrigerator, Wolf induction cooktop, Wolf double ovens, ice maker, custom Ruffino cabinetry and an oversized island flanked with granite counters. Master suite with French oak hardwood herringbone floors, en-suite marble bath plus dual walk-in closets with custom built-ins. 2 additional bedrooms with a connecting bath. Oversized 2-car garage with space for 2 vehicles plus golf cart and great storage. Gorgeous resort-style community pool and spa. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with boat shuttle plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal, billiards room, 6 Har-Tru tennis courts, bocce courts and a state of the art fitness center slated for late 2026. Preferred location just a short drive via car, bike or golf cart to downtown's 5th Avenue South and 3rd Street South known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports. Truly exceptional and a rarity to find this level of high-design and finish in a home in Windstar.

Welcome Home to 4615 Lighthouse Lane, where it's truly "Better by The Bay"! Situated in the exclusive Harrington Sound neighborhood within the amenity-rich Windstar on Naples Bay community, this unique and charming home is designed to make the most of its expansive double lot. Offering panoramic golf and lake views along with mature landscaping, this home seamlessly blends indoor and outdoor living while ensuring privacy and tranquility. With over 4,100 square feet of living space under A/C and an additional 2,190 square feet of outdoor living area, this residence is both spacious and cozy. It's thoughtfully designed for daily living, hosting friends and family, and entertaining guests of any size. The home features 4 bedrooms, 4 baths, a den, and an oversized 3-car garage. At the heart of the home lies the Great Room, where the kitchen, morning room, and family room open to the outdoor lanai, pool, spa, and a private patio retreat—ideal for enjoying Florida's beautiful weather. Soaring ceilings and recently installed hurricane-impact windows and doors flood the home with natural light. On the south end of the home, the primary suite offers direct access to the pool and breathtaking views. This suite includes a large sitting area, dual walk-in closets, and an updated spa-like bath. The adjacent den features a custom-built desk and floor-to-ceiling cabinetry, providing a perfect space for work or relaxation.VOn the north end, the visitor or guest quarters consist of three generously sized guest bedrooms, each measuring 14 x 14 feet, with two accompanying guest baths. This home is equipped with a range of special features and recent updates. It boasts a majestic circular driveway with ample guest parking, professional landscaping, a whole-house audio system, and a security system. Significant updates include newly installed hurricane impact windows and doors in 2024, an updated master bath in 2023, new HVAC and hot water heaters in 2024 and 2022, a new roof in 2021, and a new pool heater in 2025. The outdoor area is enhanced by custom-designed lanai cabinetry and a pool screen enclosure, complemented by a newly laid travertine pool deck. The modern kitchen and a gas-powered generator further add to the home's appeal. Experience the effortless elegance and comfort of this extraordinary home at 4615 Lighthouse Lane — your oasis of peace and luxury awaits! As a Windstar resident take advantage of the Keewaydin Queen’s nautical adventures (Sunset Cruises, Special Events and Private Charters) and enjoy the Windstar beach at Keewaydin Island. For additional “It’s Better by The Bay” lifestyle experiences and extensive amenities, you can join The Southpointe Yacht Club or The Windstar Club. A tour and visit to either will WOW you! “Welcome Home - It’s Better by The Bay!”

Welcome to 1560 Star Point Lane in the highly coveted enclave of Admirals Watch of Windstar on Naples Bay. Enter the lobby of this 4-unit boutique building to the elevator which opens directly into your 3 Bedroom, 3.5 Bathroom tastefully updated home in over 2600 square feet of living space under AC. Open-concept living area with walls of glass affording stunningly gorgeous western views of golf course, Naples Bay, Port Royal, Royal Harbor and sunsets. Sprawling living room with linear fireplace opens out to screened-in lanai with expansive views seamlessly blending indoor/outdoor living. A true chef's eat-in kitchen replete with shaker cabinetry, contemporary white quartz countertops, GE Monogram appliances, breakfast bar, dining area plus a sitting room with custom millwork accent wall and built-in desk area. Master Suite oasis featuring large bedroom with wall of glass overlooking the bay, dual walk-in closets with custom built-ins plus an en-suite bathroom with walk-in shower, soaking tub, dual vanities and separate water closet. Split floor plan with 2 additional guest suites each with en-suite bathrooms and views of the preserve. Full size laundry room plus a convenient powder room. Oversized 2-car garage. Gorgeous resort-style pool and spa. Deeded boat slip #7 behind the building which can accommodate up to a 30 foot boat and is just a mere 7 minutes out to the Gulf of Mexico. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with boat shuttle plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal, billiards room, 6 Har-Tru tennis courts, bocce courts and a state of the art fitness center slated for 2026 completion. Preferred location just a short drive via car, bike or golf cart to downtown's 5th Avenue known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports. This truly exceptional home has been thoughtfully updated with modern features perfect for today's paradise living. If you are looking to buy the quintessential, resort style low-maintenance home in Naples look no further!

Come discover a beautiful waterside condo with unbeatable Gulf access and a 60ft. deeded slip at Southpoint Marina just steps from your door. Inside, a newly remodeled kitchen shines with modern finishes and appliances, while a Generac generator powered by a buried propane tank adds year-round peace of mind. All of this is set within a gated community, delivering turnkey coastal living.

Windstar on Naples Bay is one of only a select few communities that seamlessly combines a premier Golf & Country Club lifestyle with a true boating community, complete with its own private marina. While separate memberships apply, Windstar stands apart as a five-star enclave, just minutes from downtown Naples and offering direct private boat access to Keewaydin Island. An iconic location paired with thoughtful design and exceptional management has created a community that continues to exceed the expectations of even the most discerning owners. Yacht Harbor Cove, situated along Southpointe Marina, enjoys captivating views of the clubhouse and an ever-changing display of beautiful yachts. Unit 204, a desirable second-floor end residence, has just undergone a full redesign and is now truly move-in ready, offering every modern comfort. The residence features: A spacious primary suite Two guest en-suite bedrooms An oversized den/flex room, ideal for an office, media room, or additional guest space From the moment you enter, your eye is drawn to the marina views and stunning natural surroundings. The open floor plan is designed for both everyday living and entertaining, with the kitchen flowing effortlessly into the living area. Enjoy formal and casual dining options, complemented by a large center island perfect for gatherings. Additional highlights include: Private elevator access directly from your two-car garage Abundant natural light from the end-unit location Thoughtful finishes and updated design throughout Windstar is nestled within the vibrant Bayshore Arts District, just off Bayshore Drive—an exciting redevelopment area now home to some of Naples’ most trendy restaurants, cafés, live music venues, boutiques, and coffee spots, all within walking distance. The highly anticipated pedestrian boardwalk, scheduled to open in February, will connect Bayshore Drive to Sugden Park, creating a greenspace experience unlike any other in Naples. There’s so much more on the horizon—and this residence places you right at the center of it all.

** Full golf membership to Windstar Club eligibility ** Welcome to 4577 Lighthouse Lane in the highly coveted enclave of Harrington Sound of Windstar on Naples Bay. This 3-4 Bedroom+den/3 Bathroom golf course house features almost 3000 square feet of light-filled living space. Large living room with soaring ceilings and wall of glass opens out to outdoor living area with pool and spa plus a built-in outdoor kitchen with expansive western vistas of the 4th fairway and stunning sunsets. Chef's eat-in kitchen replete with Bosch appliances, shaker cabinetry and granite countertops. Family room with built-ins features gorgeous views plus a lovely dining room with custom built-ins ideal for entertaining. Master suite oasis with large bedroom with access to outdoor living space, 2 walk-in closets and an updated spa-like bathroom with oversized walk-in shower, freestanding soaking tub, double vanity and separate water closet. 2 guest suites on the opposite side of the house plus updated full bathroom. Home office with a closet could be additional guest quarters plus a 3rd full bathroom. 2-car attached garage. This home is truly an entertainer's dream. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with boat shuttle plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal and Royal Harbor, billiards room, 6 Har-Tru tennis courts, bocce courts and a state of the art fitness center slated for 2026 completion. Preferred location just a short drive via car, bike or golf cart to downtown's 5th Avenue known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports.

This beautiful custom-built home features recent updates, including a new tile roof and marble-faced fireplace. IN ADDITION, THE SELLER HAS A FULLY TRANSFERABLE GOLF MEMBERSHIP! The spacious chef's kitchen has custom cabinetry, a large walk-in pantry, and newer appliances. Custom 8ft. solid core doors and premium hardware throughout. Plantation shutters and 10ft. sliding glass doors open to the pool courtyard and guest cabana, Custom lighting, skylights, a home office, a central vacuum system, and a heated pool/spa with a waterfall, are just some additional amenities to make your living here a joy. Other notable features include an AqualLink control system, storm shutters, a 2-car garage, brick pavers, and a tropical courtyard. The golf course, lake, and mangrove views from your screened lanai are stunning. Windstar has a Tom Fazio-designed golf course, and clubhouse with spectacular views of Naples Bay and 72 slip deep water marina, affording direct gulf access in less than 10 minutes. The club has clay tennis courts, a fitness center, and the Keewaydin Island Beach Club with a boat shuttle and private membership.

Your Naples Dream Home-Turnkey Furnished Luxury in Naples’ Most Exclusive Boating & Golf Community! Welcome to Regatta Landing—the newest and most sought-after enclave in Windstar on Naples Bay, where luxury living meets unmatched lifestyle perks. Built in 2021, this turnkey furnished residence spans 3,403 square feet under air and 4,437 total square feet, offering an expansive layout with four bedrooms, three full bathrooms, and multiple outdoor living spaces, including balconies and a spacious screened lanai with serene water views. Step inside to discover soaring 14-foot ceilings and an elevated coastal design throughout. The open concept floor plan features a private elevator, gourmet kitchen with oversized island, Monogram appliance package, quartz countertops, walk-in pantry, coffee bar, wet bar, and wine cooler—perfect for entertaining in effortless style. Elegant finishes like shiplap detailing add charm and warmth, while the attached two-car garage with extra storage and hurricane impact doors and windows provide both comfort and security. What truly sets this property apart is its rare offering: the option of ownership of a 38-foot dated slip in the prestigious Windstar Marina. Enjoy instant access to one of Naples’ only deep-water, private marinas, featuring a full-time harbormaster, electric/water hookups, and an exclusive marina clubhouse, all just 5 minutes to the open Gulf. Windstar on Naples Bay is a guard-gated, resort-style community offering a Tom Fazio-designed 18-hole championship golf course, tennis, a brand new state of the art fitness center opening in 2026, fine dining, a bayside clubhouse with panoramic views, and a private boat shuttle to Keewaydin Island. All this just 5 minutes to Downtown Naples, white-sand beaches, and the dynamic Bayshore Arts District, known for its thriving art scene, waterfront eateries, and local culture. Whether you’re a golfer, boater, or simply craving a move-in-ready slice of paradise—this is a rare opportunity to own the best of Naples living.

Located in Windstar on Naples Bay. Naples only gated private golf club that features both a marina and private beach on Keewaydin Island. This exceptional condo with recent updates conveys with a 30-foot boat slip equipped with a 15,000 lb lift, providing quick access to Naples Bay and the Gulf with no bridges to navigate. This condo lives like a single family home with en-suite guest rooms, one featuring its own private balcony. Its spacious open floor plan seamlessly blends elegance and comfort, perfect for both relaxation and entertaining. The oversized living space opens to the lanai which overlooks the 15th fairway and shimmering lake waters. The western exposure ensures stunning sunsets nearly every evening. Generous storage options throughout; the two-car garage includes an expansive storage area, ideal for bikes or a home gym. Windstar is distinguished as the sole private club in Naples offering golf along the bay, featuring both a marina and a private beach on Keewaydin Island. Take a day trip aboard Windstar’s boat shuttle, the *Keewaydin Queen*, to enjoy your private beach or relax on a sunset cruise. Windstar’s meticulously cared-for Tom Fazio-designed 18-hole golf course offers eight sets of tees strategically placed to cater to golfers of varying skill levels, making it Naples' premier waterfront golf course. For those who prefer socializing over golfing, members enjoy all clubhouse privileges, including access to exclusive club events, exquisite dining at all four venues, tennis, bocce, and fitness facilities. All owners at Windstar have unlimited access to the private beach and the Keewaydin boat shuttle. Experience the perfect blend of luxury and leisure in this remarkable Windstar condo—don't miss the opportunity to call it your home!

Your Naples Dream Home is ready- Turnkey Furnished Luxury in Naples’ Most Exclusive Boating & Golf Community! Welcome to Regatta Landing, the newest and most sought-after enclave in Windstar on Naples Bay, where luxury living meets unmatched lifestyle perks. Built in 2021, this professionally decorated and turnkey furnished residence spans 3,403 square feet under air and 4,437 total square feet, offering an expansive layout with four Bedrooms, three Full Bathrooms, and multiple outdoor living spaces, including balconies and a spacious screened lanai with serene views. Step inside to discover soaring 14-foot ceilings and an elevated coastal design throughout. The open concept floor plan features a private elevator, gourmet kitchen with oversized island, Monogram appliance package, quartz countertops, walk-in pantry, coffee bar, wet bar, and wine cooler making it perfect for entertaining in effortless style. Elegant finishes like shiplap detailing add charm and warmth, while the oversized attached two-car garage, with extra storage area, and hurricane impact doors and windows provide both comfort and security.Beyond the residence lies a lifestyle that is truly unmatched. Windstar on Naples Bay is a guard-gated, private country club community offering a world of amenities: a Tom Fazio–designed 18-hole championship golf course, tennis, and a soon-to-be-completed state-of-the-art fitness center overlooking the water (2026). The bayside clubhouse offers fine dining with sweeping views, while a private boat shuttle whisks you away to Windstar’s exclusive retreat on Keewaydin Island, where a pristine beach awaits. For boaters, Windstar boasts a private deepwater marina with 72 slips, private Marina Clubhouse and a full-time harbormaster. All of this is just five minutes from downtown Naples, where world-class dining, shopping, and beaches await, and right next to the Bayshore Arts District, one of the city’s most vibrant neighborhoods. This is more than a home....it’s a gateway to the ultimate Naples lifestyle.