Windstar Homes with Gated Community Type

Welcome to Windstar, a hidden gem nestled in the heart of Naples, Florida. This prestigious gated community offers an unparalleled lifestyle, combining luxury living with the breathtaking beauty of nature. Windstar is situated along the picturesque shores of Naples Bay, providing residents with stunning waterfront views and easy access to some of the finest beaches in the Sunshine State.

As you enter Windstar, you’ll be greeted by lush landscapes and meticulously maintained grounds that create a serene and inviting atmosphere. The community boasts an array of exquisite homes, each designed with elegance and comfort in mind. Whether you’re seeking a cozy villa or a sprawling estate, Windstar has something to suit every taste and preference. The architectural styles range from Mediterranean-inspired designs to modern masterpieces, ensuring that every residence feels like a personal sanctuary.

Residents of Windstar enjoy a vibrant community lifestyle, with access to a variety of amenities that cater to both relaxation and recreation. The private golf course, designed by renowned architect Tom Fazio, offers an exceptional golfing experience surrounded by stunning natural beauty. Additionally, the community features a clubhouse, tennis courts, and a marina, perfect for those who enjoy boating and fishing.

Windstar’s prime location allows for easy access to Naples’ finest dining, shopping, and entertainment options. Explore the charming boutiques of Fifth Avenue South or indulge in culinary delights at upscale restaurants, all just a short drive away. With its combination of luxury, natural beauty, and a welcoming community, Windstar is more than just a neighborhood—it’s a lifestyle waiting to be embraced. Come discover the magic of Windstar, where your dream home awaits!

Newest Windstar Homes with Gated Community Type

$695,000

3 Beds ⋅ 2 Baths ⋅ 226034256 MLS ⋅ 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

$739,000

2 Beds ⋅ 2 Baths ⋅ 226031325 MLS ⋅ Spinnaker Pointe BLDG.

One or more photo(s) has been virtually staged, AI generated or rendered. Beautifully updated and ideally positioned to capture stunning golf course and water views, this spacious first-floor residence in Spinnaker Pointe at Windstar on Naples Bay offers an inviting blend of comfort, style and effortless Florida living. The open-concept great room is enhanced by volume ceilings and abundant natural light, creating a wonderful sense of space throughout the two-bedroom, two-bath residence with an enclosed den offering valuable flexibility as a home office, additional sitting area or guest accommodations. The beautifully updated kitchen features granite countertops, stainless steel appliances and generous workspace while opening seamlessly to the main living and dining areas—equally suited for relaxed everyday living and entertaining. Updated flooring, stylish lighting and ceiling fans, fresh interior finishes and thoughtfully renovated baths further enhance the home's move-in-ready appeal. A new A/C system and water heater, both installed in 2021, provide additional peace of mind. A large laundry room with utility sink and attached garage complete the residence. One of the home's most appealing spaces is the enclosed lanai, recently enhanced with impact doors and new flooring. Framing picturesque golf course and water views, this light-filled retreat extends the living space and provides an exceptional setting for morning coffee, afternoon relaxation or evening cocktails while enjoying the peaceful surroundings. Spinnaker Pointe offers an intimate neighborhood lifestyle within Windstar, complete with its own private clubhouse, pool and spa, two tennis courts and a seasonal calendar of social activities—all just steps from the residence. Ownership in Windstar on Naples Bay provides access to one of Naples' most distinctive waterfront lifestyles, highlighted by exclusive private beach access on Keewaydin Island via the complimentary Windstar boat shuttle through the pristine waters of Rookery Bay. Residents can also enjoy sunset and full-moon cruises, while optional memberships provide access to the Tom Fazio-designed 18-hole championship golf course, dining at the renovated clubhouse and fitness amenities. A 72-slip marina further enhances Windstar's exceptional Naples Bay setting. Just minutes from Downtown Naples, celebrated beaches, exceptional dining and the vibrant Bayshore Arts District, this beautifully updated residence presents an outstanding opportunity to enjoy the best of Naples living in one of the area's most unique golf and waterfront communities.

3556 WINDJAMMER CIR Unit 1003, Naples

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 226033318 MLS ⋅ Regatta Landing BLDG.

SKIP THE WAITLIST! Windstar on Naples Bay Social Membership is available immediately with this property, offering buyers the opportunity to begin enjoying the Windstar lifestyle without the typical wait. Experience exceptional Southwest Florida living in this First-floor Coach Home in Regatta Landing, offering 2,348 square feet of spacious living with three Bedrooms, two Baths and an attached two-car Garage. Designed to live like a single-family home, this light-filled residence features a desirable split-bedroom floor plan, high ceilings, and an open-concept layout ideal for everyday living and entertaining. The spacious kitchen opens seamlessly to the main living and dining areas and features abundant cabinetry, a pantry, double ovens and a wine cooler. Significant upgrades include impact-resistant windows and doors for added peace of mind, along with an A/C system replaced in 2023. The expansive primary suite is a true private retreat, featuring generous proportions, two custom closets and a spacious primary bath with dual sinks, a soaking tub and oversized separate shower. Two additional bedrooms offer flexibility for guests, family or a home office. One of the home's standout features is the expansive oversized screened lanai, extending the living space outdoors and showcasing peaceful views across Windstar's beautifully maintained golf course. It's an exceptional setting for morning coffee, alfresco dining, entertaining or simply enjoying the Florida lifestyle. Residents of Regatta Landing enjoy a stunning private community pool and spa, along with a social grill area beautifully positioned along the waterway, creating an inviting setting to gather, entertain and enjoy Southwest Florida living. Windstar on Naples Bay offers one of Naples' most distinctive lifestyles, bringing golf, boating and beach living together within one gated community. Residents enjoy access to Windstar's private Keewaydin Island beach with boat transportation aboard the Keewaydin Queen. Optional Club membership opportunities provide access to additional amenities and experiences. Ideally located just minutes from downtown Naples, Fifth Avenue South, Third Street South, exceptional dining, shopping and Naples' renowned Gulf beaches, this residence presents an outstanding opportunity to enjoy the highly sought-after Windstar on Naples Bay lifestyle. Membership is optional, subject to Club approval, and requires a separate purchase.

2534 Windward CT Unit 15-101, Naples

$899,000

3 Beds ⋅ 2 Baths ⋅ 226033247 MLS

EXPANSIVE WATER AND GOLF COURSE VIEWS set the stage for this beautifully updated Somerset villa in highly sought-after Windstar on Naples Bay. Offering 1,833 square feet under air and 2,464 total square feet, this 3-bedroom, 2-bath residence combines the ease of villa living with the privacy and feel of a single-family home. An exceptional floor plan blends comfort and functionality, while the updated kitchen features custom wood cabinetry, Bosch stainless steel appliances and granite countertops. Freshly painted in a neutral color palette, additional features include wood flooring, plantation shutters, hurricane impact-resistant windows and doors, and a 2025 HVAC system. The large screened lanai showcases peaceful lake views extending across Windstar’s 13th hole, creating a beautiful backdrop for relaxing and entertaining. Lush tropical landscaping surrounds the brick-paver driveway and side walkway, while an attached 2-car garage with epoxy floor provides additional convenience. Ideally located just across from Somerset’s heated community pool and spa, this pet-friendly neighborhood also offers low HOA fees. Windstar residents enjoy access to a private beach on Keewaydin Island with boat shuttle service, while membership opportunities provide access to championship golf, tennis, fitness, dining, social amenities and Windstar’s private deep-water marina with direct Gulf access. All just minutes from downtown Naples, Fifth Avenue South, beaches and the Bayshore Arts District. Some photos have been virtually staged for visualization purposes only.

2153 Paget CIR Unit 1, Naples

$649,900

3 Beds ⋅ 2 Baths ⋅ 226030259 MLS ⋅ 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 ⋅ 226032840 MLS ⋅ 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

$749,000

2 Beds ⋅ 2 Baths ⋅ 226032827 MLS ⋅ Marina Cove BLDG.

Welcome to Marina Cove at Windstar on Naples Bay. This 2-bedroom plus den, 2-bath coveted end unit offers the spacious feel and privacy of a single-family home. The open-concept living area features a chef-inspired eat-in kitchen with stainless steel appliances, white cabinetry, contemporary countertops and island, flowing seamlessly into the spacious living and dining areas. Expansive glass doors open to a large screened lanai, creating effortless indoor-outdoor living while showcasing beautiful views of lush green space, lakes, the golf course, mature trees and spectacular sunsets. The primary suite is a private retreat featuring a spacious bedroom, walk-in closet with custom built-ins and spa-like bath with a walk-in shower, double vanity and private water closet. A guest bedroom, versatile den, full guest bath and convenient laundry complete the interior, while an attached 2-car garage provides exceptional storage and convenience. Windstar on Naples Bay offers a lifestyle unlike any other gated golf community in Naples, featuring a Tom Fazio-designed 18-hole golf course, direct access to Naples Bay, a private 6-acre beach on Keewaydin Island with boat shuttle service from the Windstar dock and a full-service 73-slip deep-water marina. The newly renovated clubhouse, available with separate club membership, features multiple dining venues overlooking Naples Bay and Port Royal, a billiards room, six Har-Tru tennis courts, bocce courts and a state-of-the-art fitness center. Ideally located less than 10 minutes from downtown Naples and renowned Fifth Avenue South with its exceptional dining, shopping and nearby Gulf beaches. Naples Botanical Garden and the East Naples pickleball complex are also nearby, with convenient access to I-75 and both Naples and Southwest Florida International airports.

5015 MARINA COVE DR Unit 203, Naples

$1,295,000

2 Beds ⋅ 2.5 Baths ⋅ 226031090 MLS ⋅ Regatta Landing BLDG.

Welcome to 2439 Breakwater Way, Unit 9102 — a beautifully upgraded coach home in Regatta Landing, the newest enclave within the prestigious Windstar on Naples Bay community. This isn't just a home, it's a front-row seat to the boating, golf, and coastal lifestyle Naples is known for. Spanning over 2,600 square feet, this first-floor residence lives large with 2 bedrooms plus a den, 2.5 baths, and a 2-car attached garage. From the moment you walk in, quality is evident: beautiful French Oak hardwood floors run throughout, complemented by crown molding, plantation shutters, and frameless shower doors that elevate every room. The kitchen is a showpiece — stainless KitchenAid appliances, double wall ovens, quartz counters, and under-cabinet lighting come together for a space built for both everyday living and serious entertaining. Step out onto the spacious, fully enclosed lanai and take in tranquil canal and mangrove views — a private, peaceful backdrop that's hard to find this close to the water. Upgraded with glass doors, the lanai stays cool and comfortable year-round while offering the feel of an outdoor living space. Boat dock with lift options are available for purchase just steps behind the home, offering a short ride straight out to Naples Bay and the Gulf of Mexico. Beyond your door, Windstar delivers a resort-caliber lifestyle: a gated, boating and golf community with tennis courts, and a community pool, spa, and grill room just a short walk away. Built in 2017 and offered with quality upgrades throughout, this is a rare opportunity to own in one of Naples' most sought-after waterfront communities — where boating, golf, and bay views come standard.

2439 Breakwater WAY Unit 9102, Naples

$1,700,000

3 Beds ⋅ 2.5 Baths ⋅ 226031232 MLS

Welcome to 3852 Clipper Cove Drive, a beautifully designed 3-bedroom, 3-bathroom residence offering spacious living, exceptional entertaining areas, and a private pool facing south and overlooking the 10th hole of the golf course. Complete with an oversized 2-car garage, this home combines everyday functionality with the relaxed lifestyle Naples is known for. The main-floor owner’s suite creates a private retreat with a generous walk-in closet and large en-suite bathroom, providing the convenience and comfort of main-level living. Throughout the home, expansive gathering and entertaining spaces provide plenty of room to host family and friends while still offering comfortable separation for guests. The living areas flow naturally toward the outdoor space, where the pool and golf course setting become an extension of the home. Spend afternoons poolside, entertain guests in the Florida sunshine, or unwind in the evening while overlooking the 10th hole. With 3 bedrooms, 3 bathrooms, an oversized 2-car garage, a main-floor owner’s suite, generous entertaining spaces, and a private pool overlooking the golf course, 3852 Clipper Cove Drive offers an exceptional opportunity to enjoy the Naples lifestyle both inside and out.

3852 Clipper Cove DR, Naples

$2,795,000

3 Beds ⋅ 3.5 Baths ⋅ 226028395 MLS ⋅ Admirals Watch BLDG.

Welcome to 1600 Star Point Lane in the highly coveted enclave of Admirals Watch of Windstar on Naples Bay. Enter the elegant lobby of this 4-unit boutique building to the elevator which opens directly into your 3 Bedroom, 3.5 Bathroom tastefully updated home in nearly 2800 square feet of living space. Open-concept living area with walls of glass affording stunningly gorgeous western views of golf course, Naples Bay, Port Royal, Royal Harbor and sunsets. A true chef's eat-in kitchen replete with contemporary white quartz countertops, stainless steel appliances, breakfast bar, dining area plus a sitting room with lovely fireplace. Master Suite oasis featuring large bedroom with wall of glass overlooking the bay, dual walk-in closets with custom built-ins plus an updated en-suite bathroom with walk-in shower, soaking tub, dual vanities and separate water closet. Split floor plan with 2 additional guest suites (1 is set up as home office) each with en-suite bathrooms and views of the preserve. Full size laundry room plus a convenient updated powder room. Lovely terrace provides additional outdoor living space. Oversized 2-car garage. Gorgeous resort-style 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. 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!

1600 STAR POINT LN Unit 2-201, Naples

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windward Cay BLDG.

Skip Windstar's 7-year golf waitlist — full golf membership transfers at closing. Windstar on Naples Bay caps golf membership at 350. The waitlist currently runs approximately seven years. This sale is the shortcut: seller relinquishes their full golf membership at closing, giving the buyer immediate access to the Tom Fazio championship course, clubhouse, and practice facility — no waitlist (initiation fee and dues apply). The home: fully furnished 3BR/3BA two-story townhouse with den and 1-car garage, directly on the golf course inside Windstar's private gates — Naples' only gated golf community with direct bay access, a private marina, and its own beach on Keewaydin Island. The water: deeded Boat Slip #13 at Southpointe Yacht Club — deep-water marina fully rebuilt in 2023 with new pilings and composite docks. Direct Naples Bay and Gulf access, no bridges. Slip ownership includes private marina pool/spa and common area. Golf in the morning. Gulf by afternoon. Home on the course. One closing delivers all three. Furnished. Move-in ready.

4700 Yacht Harbor DR Unit 622, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS ⋅ Windward Cay BLDG.

Discover exceptional value and an unbeatable lifestyle in this beautifully maintained first-floor residence located in the prestigious gated community of Windstar on Naples Bay. Offering nearly 1,800 square feet of thoughtfully designed living space, this 2-bedroom, 2-bathroom condo with a den features soaring vaulted ceilings, crown molding, plantation shutters, and an attached one-car garage. Perfectly positioned just steps from the community pool, the screened lanai overlooks lush tropical landscaping and the picturesque 7th tee, creating a peaceful backdrop that perfectly complements the community's renowned golf lifestyle. A fully paid reverse osmosis water treatment system provides an added level of comfort and value. Windstar is one of Naples' most exclusive communities, offering a rare combination of championship golf and direct Gulf access. Residents enjoy a private boat shuttle to Keewaydin Island, a 72-slip deep-water marina, and a beautifully redesigned clubhouse with waterfront dining overlooking Naples Bay. The community also features tennis, bocce, a state-of-the-art fitness center, and a vibrant social calendar, with residents receiving priority on the waitlist for Social and Social Summer Golf Memberships. Ideally located just minutes from the vibrant Bayshore Arts District, Naples Botanical Garden, and less than four miles from the world-class dining, shopping, and white sand beaches of 5th Avenue South, this home offers the perfect opportunity for full-time living, a seasonal retreat, or an exceptional investment in one of Naples' most desirable waterfront communities.

4700 Yacht Harbor DR Unit 612, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.