Windward Cay Homes with Gated Community Type

Welcome to Windward Cay, a serene gated community nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming neighborhood is a hidden gem that perfectly balances luxury living with a warm, welcoming atmosphere.

Windward Cay features an array of beautifully designed homes that cater to a variety of lifestyles, from families seeking a spacious haven to retirees looking for a peaceful retreat. Each residence boasts modern amenities, stylish interiors, and lush landscaping, providing an idyllic backdrop for your Florida dream home. The community is designed with your comfort in mind, offering a blend of privacy and camaraderie among neighbors.

One of the standout features of Windward Cay is its secure gated access, ensuring peace of mind for residents. As you enter the community, you’ll be greeted by beautifully manicured grounds and a sense of tranquility that sets this neighborhood apart. The community is also conveniently located near Naples' renowned beaches, upscale shopping, and fine dining, allowing residents to enjoy the best of Florida living just moments from their doorstep.

For those who love outdoor activities, Windward Cay is ideally situated near lush parks, scenic golf courses, and pristine nature trails, providing endless opportunities for exploration and recreation. Whether you’re strolling through the neighborhood or enjoying a sunset at the nearby beach, Windward Cay offers a lifestyle that is both vibrant and relaxed.

Discover the charm of Windward Cay, where your dream home awaits amidst the natural beauty and luxurious amenities of Naples, Florida. Welcome home!

Newest Windward Cay Homes with Gated Community Type

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS

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 Drive Unit 622, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS

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 Drive Unit 612, Naples

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