Windward Cay Real Estate

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida. This charming community offers an idyllic blend of tranquility and convenience, making it the perfect place to call home. With its lush landscaping and picturesque surroundings, Windward Cay embodies the essence of Florida living.

Located in Collier County, Windward Cay is just minutes away from Naples’ stunning beaches, vibrant shopping districts, and gourmet dining options. Residents can enjoy easy access to the renowned Fifth Avenue South, where boutique shops and art galleries await. The community is also in close proximity to the natural beauty of the Everglades, offering endless opportunities for outdoor adventures and exploration.

Windward Cay features a variety of well-appointed homes, each designed with comfort and style in mind. Whether you’re looking for a cozy villa or a spacious family home, you’ll find the perfect fit within this welcoming neighborhood. Many properties boast private outdoor spaces, ideal for entertaining or simply soaking up the Florida sunshine.

For those seeking an active lifestyle, Windward Cay offers a range of amenities, including swimming pools, tennis courts, and walking paths that encourage a sense of community and well-being. The friendly atmosphere makes it easy to connect with neighbors and create lasting friendships.

With its prime location, beautiful homes, and community-oriented spirit, Windward Cay is more than just a place to live; it’s a lifestyle. Come experience the magic of Naples and discover why Windward Cay is the perfect choice for your next home.

Newest Listings in Windward Cay

$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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