Windstar Homes for Sale in Naples, FL

Windstar on Naples Bay: Golf, Marina, and Beach Club in One Gated Community

Windstar on Naples Bay occupies a singular position in Southwest Florida real estate: it is the only gated golf community in Naples that also offers a private deep-water marina and its own beach club. Spread across approximately 450 acres along Naples Bay — near the Bayshore Arts District and directly across from the Naples Botanical Garden, just minutes from downtown Naples — this guard-gated community of 554 residences across 15 distinct neighborhoods delivers a combination no other address can match: championship golf, serious boating, and private beach access, all behind one set of gates.

Lifestyle & Location

Nearly 40 percent of Windstar's acreage is preserved green space, giving the community a peaceful, natural character unusual for its central location. Mature landscaping, lakes, and waterfront settings surround a diverse collection of condominiums, coach homes, villas, single-family homes, and waterfront estates. Downtown Naples' Fifth Avenue South dining and shopping is about a mile away, the vibrant Bayshore Arts District sits just outside the gates, and Southwest Florida International Airport is an easy drive — a level of convenience few private club communities can claim.

Homes & Real Estate

Windstar's 15 neighborhoods offer genuine choice, from low-maintenance condominiums and coach homes to spacious single-family residences and custom waterfront estates with bridge-free Gulf access. The community's newest enclave, Regatta Landing, showcases the modern coastal luxury the market increasingly demands. Whether you seek a lock-and-leave condo near the marina, a golf-course villa, or a bay-view estate, Windstar's range of housing types and price points makes it one of Naples' most versatile luxury addresses. Many residences are oriented toward water, golf, or preserve views, with tropical landscaping and lake settings throughout the 450-acre grounds.

The location adds another dimension entirely. Windstar sits in the heart of the Bayshore Arts District — one of Naples' most vibrant, walkable neighborhoods — with the celebrated Naples Botanical Garden directly across the street, the Naples Pickleball Center nearby, and Celebration Park's food-truck scene reachable by boat. It's an unusual and appealing blend: a guard-gated private club community wrapped in greenery, with an artsy, energetic district right outside the gates and downtown Naples' Fifth Avenue South about a mile away. Few Naples addresses combine this level of privacy with this level of walkable, waterfront-adjacent energy.

Amenities: Golf, Marina & Beach Club

The amenity package is the headline. Golfers enjoy an 18-hole Tom Fazio-designed championship course (par 72, playing over 6,700 yards) with eight sets of tees for all skill levels. Boaters have the private Southpointe Marina — a 72-slip deep-water marina accommodating vessels up to approximately 70 feet, with a marina clubhouse, full-time harbormaster, and direct access to Naples Bay and the Gulf. Club members also enjoy a private beach retreat on Keewaydin Island, reached by boat shuttle, plus a 33,000-square-foot clubhouse with dining overlooking the bay, six lighted Har-Tru tennis courts, bocce courts, a resort-style swimming pool, and a state-of-the-art fitness center.

Notably, Windstar is not a bundled-golf community: purchasing a home does not automatically require club membership, so buyers can separate the residential decision from the club decision and choose the membership level that fits their lifestyle — from social and dining privileges to full golf.

For boaters who golf, golfers who boat, and everyone who wants waterfront living minutes from downtown Naples, Windstar on Naples Bay is simply unmatched. It's a rare combination — private marina, championship golf, beach club, and Bayshore energy — that no other Naples community replicates. Call OS Florida Group at (239) 216-2016 to explore current Windstar listings across all 15 neighborhoods.

Newest Windstar Listings

$1,099,000

2 Beds ⋅ 2 Baths ⋅ 2,185 SqFt. ⋅ Windward Cay BLDG.

Welcome to 4600 Yacht Harbor Drive in Windward Cay at Windstar on Naples Bay, one of Naples’ most desirable gated waterfront communities. This beautifully renovated, furnished end-unit residence offers 2 bedrooms plus a den, 2 full bathrooms, and approximately 2,185 square feet of inviting living space with tranquil golf course views. Rich hardwood flooring, solid-core doors, crown molding, plantation shutters, custom lighting, and thoughtfully selected finishes create a warm, refined interior. The expansive chef’s kitchen features custom cabinetry, granite countertops, a beautiful backsplash, an induction cooktop, a pot filler, and generous storage, making it equally suited to everyday living and entertaining. The spacious primary suite provides a peaceful retreat with custom closet built-ins and a beautifully appointed bathroom. Additional highlights include a formal dining room, a versatile den ideal for a home office or additional guest space, custom window treatments, a stackable washer and dryer, and an approximately 8-by-6-foot storage room. Overlooking Windstar’s picturesque 8th fairway, the residence enjoys a serene backdrop of lush tropical landscaping and beautifully maintained greens. Windward Cay residents enjoy a heated community pool, grilling area, elevator access, and an intimate residential setting. Windstar on Naples Bay offers an exceptional collection of amenities, including a Tom Fazio-designed 18-hole golf course, driving range, and a newly renovated clubhouse with spectacular Naples Bay views. The brand-new, recently completed fitness center adds another highlight to the community’s active lifestyle, complementing its tennis courts and bocce facilities. A full-service deep-water marina with direct Gulf access enhances the waterfront experience, while a seasonal boat shuttle to Windstar’s private beach on Keewaydin Island offers a secluded Gulf-front escape. Golf and clubhouse memberships are available separately, subject to availability and club requirements. Ideally located just minutes from downtown Naples, Fifth Avenue South, Third Street South, acclaimed dining, shopping, and Gulf beaches, Windstar also offers convenient access to the Bayshore Arts District, Naples Botanical Garden, and Naples Pickleball Center. For buyers considering The Moorings, Park Shore, or Gulf Shore Boulevard, Windstar presents a compelling opportunity to enjoy a gated waterfront community with exceptional amenities, natural beauty, and proximity to everything Naples has to offer. Discover beautifully renovated interiors, peaceful golf course views, and the best of the Southwest Florida lifestyle. One or more photos have been virtually staged, AI-generated, or rendered.

4600 Yacht Harbor DR Unit 412, Naples

$649,000

2 Beds ⋅ 2 Baths ⋅ 1,589 SqFt. ⋅ Windward Cay BLDG.

Golf Course Views and Private Beach Access on Naples Bay! Welcome to this completely updated, second-floor gem in the prestigious Windstar on Naples Bay community. Offering 1,589 square feet of thoughtfully curated living space, this move-in ready 2-bedroom-plus-den features a new custom-built Murphy bed that seamlessly transforms the space into an immediate third guest suite. This residence has been beautifully modernized throughout and delivers the ultimate Southwest Florida lifestyle with absolutely zero post-closing work required. Start your day with coffee on your private lanai overlooking the pristine greens on the 7th hole, relax by the expansive community pool, or embark on a waterfront adventure aboard Windstar's private shuttle boat, the Keewaydin Queen, which takes residents directly to a private island beach. Ideally located just 10 minutes from downtown Naples and historic Olde Naples, you will enjoy effortless daily access to world-renowned dining, luxury shopping, entertainment, and the distinct charm of Fifth Avenue South. Whether you are seeking a full-time residence, an effortless seasonal retreat, or a prime investment opportunity, this condo offers an exceptional blend of modern updates, flexible living space, scenic golf views, and stunning daily sunsets. Experience championship golf along the bay, boating adventures, and exclusive beach access all in one remarkable, highly sought-after Naples community.

4650 Yacht Harbor DR Unit 124, Naples

$699,000

3 Beds ⋅ 3 Baths ⋅ 2,288 SqFt. ⋅ Spinnaker Pointe BLDG.

RARE OPPORTUNITY! 3 BEDROOMS PLUS DEN, 3 FULL BATHS, AND ALMOST 2,300 SQ. FT. OF LIVING SPACE IN SPINNAKER POINTE AT WINDSTAR ON NAPLES BAY! Spectacular golf course views of Windstar's Hole #12 and long water views, exceptional living space, and the ultimate Naples lifestyle await! This beautifully maintained, FURNISHED residence features a PRIVATE ELEVATOR, attached one-car garage, and an inviting floor plan designed for comfortable Florida living. Soaring vaulted ceilings and plantation shutters throughout create a bright, open atmosphere, while the versatile den offers endless possibilities as an additional living area, home office, or media room. The expansive primary suite is a true retreat, showcasing beautiful golf course and water views, two closets, and a spacious bath complete with dual vanities, a soaking tub, and a large walk-in shower. A private en-suite guest bedroom offers additional comfort and privacy for family and visitors. The well-appointed kitchen features quartz countertops, a center island, and a walk-in pantry, providing the perfect combination of style and functionality. Step onto the screened lanai and take in the spectacular golf course and tranquil water views, complete with electric storm shutters for added convenience and protection. Recent improvements include a brand-new storm-rated front door with sidelights, carpeting just one year old, and an HVAC system approximately two years old. Spinnaker Pointe offers its own community pool, tennis courts, and clubhouse, creating an inviting neighborhood setting. Beyond your doorstep, discover the extraordinary lifestyle of WINDSTAR ON NAPLES BAY, featuring access to a private beach experience on beautiful Keewaydin Island with daily boat shuttle service, along with optional club membership opportunities. Perfectly situated in Naples' vibrant BAYSHORE ARTS DISTRICT, enjoy nearby waterfront dining, art galleries, the Naples Botanical Garden, and an exciting collection of local attractions. All this, just approximately 1.5 miles from downtown Naples and its world-renowned beaches! An exceptional opportunity to enjoy the space, convenience, breathtaking views, and coastal lifestyle that make Windstar on Naples Bay so desirable!

3560 Windjammer CIR Unit 1104, Naples

$439,000

2 Beds ⋅ 2 Baths ⋅ 1,561 SqFt. ⋅ Marina Cove BLDG.

Discover the appeal of waterfront living in this beautifully maintained first floor coach home in Marina Cove, ideally located just steps from the Windstar Marina and Yacht Basin. The inviting open layout features a bright kitchen with a cozy breakfast nook, crown molding, and diagonally laid tile flooring. French doors lead to a spacious screened lanai, offering a relaxing setting to enjoy peaceful lake and fountain views. An attached garage, brick paver driveway, and lush tropical landscaping add to the home’s charm and convenience. Marina Cove residents enjoy a welcoming neighborhood atmosphere, along with a heated community pool, spa, and private clubhouse. Within the sought after Windstar on Naples Bay community, optional memberships offer access to an exceptional collection of amenities, including a beautifully renovated clubhouse overlooking Naples Bay and Port Royal, newly built state-of-the-art fitness center, an active social calendar, the 73 slip deep water marina at Southpointe Yacht Club, six Har Tru tennis courts, and three bocce courts. Enjoy access to Keewaydin Island Beach Club via the private Keewaydin Queen boat shuttle, as well as private sunset, fishing, and sightseeing cruises aboard the Second Wind. Conveniently located near Naples Botanical Garden, the Bayshore Arts District, and the Naples Pickleball Center, with the renowned shopping, dining, and entertainment of 5th Avenue South and 3rd Street South just a short drive away. Experience the relaxed coastal lifestyle of Marina Cove and the many opportunities that come with being part of Windstar on Naples Bay.

5060 Yacht Harbor CIR Unit 102, Naples

$625,000

2 Beds ⋅ 2 Baths ⋅ 1,822 SqFt. ⋅ Marina Cove BLDG.

Extensively renovated 2-bedroom + den coach home offering preserve views and a spacious screened lanai ideal for relaxing or entertaining. The residence features plantation shutters, gorgeous luxury vinyl plank (LVP) and tile flooring, and a beautifully redesigned kitchen with a center island, stainless steel appliances, wine refrigerator, abundant cabinetry, and generous workspace. The extensive remodel also includes updated three-panel interior doors, new door casings, baseboards, and trim throughout, adding a clean, finished look to the home. The thoughtfully renovated bathrooms feature frameless glass shower enclosures and stylish finishes that complement the home’s warm, sophisticated feel. Ideally situated in close proximity to the Marina Cove heated pool, spa, and private clubhouse, with the Windstar Marina just a short walk away, this residence enjoys a convenient location within the community. Offered furnished, it presents a wonderful opportunity to begin enjoying the Windstar lifestyle right away. Windstar offers exceptional amenities including a Tom Fazio–designed golf course, newly redesigned clubhouse with sweeping views of Naples Bay, 72-slip deep-water marina with direct Gulf access in under ten minutes, clay tennis courts, bocce ball, newly built state-of-the-art fitness center, and private Windstar boat shuttle to Keewaydin Island’s white sandy beach featuring a shaded pavilion, restrooms, and exceptional shelling & fishing!

5035 Yacht Harbor DR Unit 203, Naples

$689,000

2 Beds ⋅ 2 Baths ⋅ 1,711 SqFt. ⋅ Morningstar BLDG.

An extraordinary transformation in the prestigious Morningstar enclave of Windstar on Naples Bay, this spectacular corner residence offers a rare combination of sophisticated architectural design, uncompromising craftsmanship and breathtaking panoramic views. 2 car spaces. Completely reimagined in 2022 with an extensive, no-expense-spared renovation, this exceptional residence captures an impressive 270-degree panorama encompassing shimmering lakes, lush golf course fairways and pristine mangrove preserves, with both eastern and western exposures providing an ever-changing backdrop of natural beauty. Soaring ceilings, exquisite custom detailing and wide-plank light oak flooring establish an atmosphere of understated elegance throughout the beautifully appointed interiors. Designed for effortless entertaining, the expansive open-concept living area is anchored by a stunning chef’s kitchen featuring bespoke cabinetry, premium quartz countertops, a generous center island, stainless steel appliances and a dedicated wine refrigerator. An architectural coffered ceiling adds distinction to the dramatic great room, where expansive glass doors open to an oversized lanai, creating a seamless connection between refined interior spaces and the spectacular surrounding landscape. The luxurious primary retreat offers a tranquil sanctuary with a custom beamed ceiling, beautifully organized walk-in closet and elegantly appointed ensuite bath, complemented by a thoughtfully designed adjoining laundry room with custom cabinetry and side-by-side appliances. A generously proportioned guest bedroom with custom closet, beautifully finished guest bath and discreetly integrated private office nook provide exceptional comfort and versatility. Every element reflects an unwavering commitment to quality, including impact-resistant windows and doors, solid-core interior doors, a newer HVAC system and tankless water heater. Beyond the residence, Windstar enjoys an enviable location within Naples’ flourishing Bayshore Arts District, moments from Naples Botanical Garden and the renowned US Open Pickleball Championships venue at East Naples Community Park. The celebrated boutiques, acclaimed restaurants and pristine Gulf beaches of downtown Naples and Fifth Avenue South are just a short drive, bicycle ride or golf cart excursion away. Offering the sophistication of a custom-designed luxury residence within one of Naples’ most distinctive waterfront communities, this remarkable property delivers an exceptional opportunity to experience the very best of Southwest Florida living.

3615 HALDEMAN CREEK DR Unit 204, Naples

$449,000

2 Beds ⋅ 2 Baths ⋅ 1,561 SqFt. ⋅ Marina Cove BLDG.

Experience the perfect blend of coastal elegance, tranquil waterfront views, and an exceptional Naples location in this beautifully updated coach home in Marina Cove. Ideally positioned with coveted southern exposure, this light-filled residence offers two bedrooms, two baths, and an inviting open layout designed for effortless Florida living. Expansive sliding glass doors fill the interiors with natural light while framing picturesque views of the sparkling lake and fountain, creating a seamless connection to the oversized screened lanai—an idyllic setting for morning coffee, alfresco dining, or simply enjoying the peaceful waterfront surroundings. The beautifully appointed kitchen features crisp white solid-surface countertops, stainless steel appliances, and a fresh, contemporary aesthetic. Thoughtfully situated just steps from the community pool, clubhouse, and convenient guest parking, this residence offers an exceptional combination of privacy, accessibility, and resort-inspired living. Residents enjoy an extraordinary coastal lifestyle with access to seven miles of private beach, while the renowned shopping, fine dining, galleries, and entertainment of downtown Naples' iconic Fifth Avenue South are just minutes away. Whether envisioned as a seasonal retreat or a year-round residence, this inviting waterfront haven captures the essence of sophisticated, carefree Naples living.

5040 YACHT HARBOR CIR Unit 102, Naples

$695,000

3 Beds ⋅ 2 Baths ⋅ 1,700 SqFt. ⋅ Marina Cove BLDG.

Beautifully updated first-floor, three-bedroom coach home with a spacious screened lanai showcasing tranquil lake and fountain views. This professionally decorated, furnished residence features plantation shutters, a beautifully redesigned kitchen with a large center island, cooktop, wall oven, stainless steel appliances, wine refrigerator, and abundant cabinetry. Additional highlights include recently installed impact-resistant windows and doors and electric sunshades on the lanai, creating an inviting outdoor living space to enjoy throughout the day. The thoughtfully updated bathrooms include frameless glass shower enclosures, while gorgeous wood and tile flooring extends throughout the home, creating a warm, sophisticated feel. Ideally located directly across from the Windstar Marina, Marina Cove offers a sparkling heated pool and spa, private clubhouse, and exceptional curb appeal. Being offered furnished, this is a wonderful opportunity to begin enjoying the Windstar lifestyle immediately. Windstar offers exceptional amenities including a Tom Fazio–designed golf course, newly redesigned clubhouse with sweeping views of Naples Bay, 72-slip deep-water marina with direct Gulf access in under ten minutes, clay tennis courts, bocce ball, newly built state-of-the-art fitness center, and private Windstar boat shuttle to Keewaydin Island’s white sandy beach featuring a shaded pavilion, restrooms, and exceptional shelling & fishing!

5075 Yacht Harbor DR Unit 103, Naples

$639,900

3 Beds ⋅ 2 Baths ⋅ 1,700 SqFt. ⋅ Marina Cove BLDG.

Indulge in refined coastal living within the prestigious gates of Windstar Country Club, one of Naples’ most coveted waterfront communities: Perfectly positioned first-floor end unit residence (with 2 car garage!), this exceptional home captures breathtaking views of the golf course and water while offering a rare sense of privacy and tranquility. Comfortable and inviting, the three-bedroom layout offers a desirable split-bedroom design, a private two-car attached garage, and a spacious kitchen with a center island and sunny breakfast nook that creates an easy gathering place for casual meals and conversation. Elegant crown molding, and timeless plantation shutters elevate the home with a level of sophistication synonymous with luxury Naples living. Peace of mind meets modern efficiency with recent high-value improvements, including an HVAC system just 4 months old (with warranty), a brand-new water heater, a new stainless steel refrigerator, and a one-year-old dishwasher—ensuring both comfort and confidence for years to come. Ideally located just minutes from the sugar-sand beaches of the Gulf and the world-class boutiques and dining of Old Naples and the Bayshore District, this residence offers the perfect balance of serenity and accessibility. Windstar delivers an unmatched lifestyle, highlighted by exclusive access to a private beach on Keewaydin Island via twice-daily shuttle. Optional membership unlocks a wealth of premier amenities, including a championship golf course masterfully designed by Tom Fazio, Har-Tru tennis courts, a state-of-the-art fitness center, and exceptional dining experiences. For boating enthusiasts, the community’s exclusive 72-slip deep-water marina—offering slips for purchase or lease—completes this extraordinary offering, setting Windstar apart as one of Naples’ only gated golf communities with direct boating access. This is more than a home—it’s an opportunity to enjoy the Windstar lifestyle, where an exceptional location, beautiful surroundings, and resort-style amenities come together.

5015 Marina Cove DR Unit 103, Naples

$549,000

2 Beds ⋅ 2 Baths ⋅ 1,414 SqFt. ⋅ Compass Point South BLDG.

Welcome to Compass Point at Windstar on Naples Bay. This thoughtfully renovated 2 bedroom/2 bath coveted first floor end unit feels more like a house. Open-concept living space including a chef's like eat-in kitchen with stainless steel appliances, white shaker cabinetry and granite countertops. Spacious living room/dining room with wall of sliding glass doors opening out to lanai seamlessly blending indoor/outdoor living. Gorgeous views of 17th fairway, lake, mature trees and sunsets. Master suite oasis including spacious bedroom, walk-in closet with custom built-ins, spa-like bath with oversized walk-in shower and double vanity. Great size guest bedroom plus hall bathroom and convenient laundry 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 6-acre beach on Keewaydin Island with boat shuttle from Windstar dock plus a full service 73-slip deep water marina. Newly renovated club (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 new state of the art fitness center. Convenient location less than a 10 minute drive to downtown's 5th Avenue renowned for its fine dining, shopping and beaches. Close to Naples Botanical Garden and Naples pickleball center. Easy access to I-75, Naples and Fort Myers airports. Simply move right in for season!

3554 HALDEMAN CREEK DR Unit 111, Naples

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