Windward Cay Real Estate

Welcome to Windward Cay, a picturesque subdivision nestled in the heart of Naples, Florida, within the serene Collier County. This charming community offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone seeking a slice of paradise.

Windward Cay is renowned for its lush landscaping, vibrant tropical flora, and well-maintained properties that create a warm and inviting atmosphere. Residents enjoy the peaceful ambiance, with many homes featuring stunning views of serene lakes and nature preserves, providing a perfect backdrop for your daily life. The neighborhood is designed with a focus on community, where friendly neighbors often gather for social events or simply to enjoy the beautiful Florida weather.

One of the standout features of Windward Cay is its prime location. Just a short drive away, you’ll find Naples’ world-famous beaches, upscale shopping at the Waterside Shops, and an array of gourmet dining options. Outdoor enthusiasts will appreciate the proximity to beautiful parks, golf courses, and nature trails that encourage an active lifestyle.

Families will also find top-rated schools nearby, ensuring a quality education for their children. With its close-knit community feel and convenient access to Naples’ vibrant cultural scene, Windward Cay truly offers the best of both worlds.

Whether you're looking to invest in a vacation home or seeking a permanent residence, Windward Cay is a community that promises not just a home, but a lifestyle filled with sunshine, warmth, and endless opportunities for relaxation and recreation. Come discover your dream home in this enchanting Naples neighborhood!

Newest Listings in Windward Cay

$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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