Windward Cay Homes with Gated Community Type

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida, within the vibrant Collier County. This charming gated community offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle in one of Florida's most sought-after locales.

Windward Cay boasts beautifully designed homes that reflect the essence of coastal living. Each residence is thoughtfully crafted with spacious layouts, contemporary finishes, and lush landscaping, providing an inviting atmosphere for both relaxation and entertainment. Many homes feature private backyards, perfect for enjoying the warm Florida sun or hosting gatherings with friends and family.

As a gated community, Windward Cay offers an added layer of security and privacy, allowing residents to feel safe and at ease in their surroundings. The community is well-maintained and features amenities that cater to an active lifestyle, including walking paths, recreational areas, and nearby parks. Residents can take advantage of the stunning beaches, world-class shopping, and exquisite dining options that Naples is renowned for, all just a short drive away.

Windward Cay is not just a place to live; it’s a lifestyle choice that embraces the best of Florida living. Whether you're looking to enjoy the vibrant community spirit or seeking a peaceful retreat, Windward Cay is the perfect place to call home. Discover the charm and convenience of this exceptional gated community, where your dream home awaits!

Newest Windward Cay Homes with Gated Community Type

$1,375,000

3 Beds ⋅ 3 Baths ⋅ Windward Cay SubDv.

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 ⋅ Windward Cay SubDv.

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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