Windward Cay Homes with Gated Community Type

Welcome to Windward Cay, a stunning gated community nestled in the heart of Naples, Florida, within the picturesque Collier County. This exclusive neighborhood offers a perfect blend of luxury, tranquility, and convenience, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle in one of the most sought-after areas of Southwest Florida.

Windward Cay boasts a collection of beautifully designed homes that reflect the charm and elegance of coastal living. Each residence is thoughtfully crafted, featuring spacious floor plans, modern amenities, and lush landscaping that enhances the natural beauty of the surroundings. Whether you’re looking for a cozy single-family home or a more expansive property, Windward Cay has something to suit every taste and lifestyle.

As a gated community, Windward Cay provides an added layer of security and privacy, allowing residents to enjoy peace of mind while they unwind in their own personal oasis. The community is also conveniently located near Naples’ world-class shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away.

Outdoor enthusiasts will appreciate the proximity to pristine beaches, scenic parks, and vibrant golf courses that Naples is known for. With year-round sunshine, residents can indulge in a variety of recreational activities, from boating and fishing to biking and hiking.

Discover the charm of Windward Cay, where luxury living meets a relaxed Florida lifestyle. Come home to a community that embodies the essence of Naples, and experience the perfect blend of comfort, style, and security. Your dream home awaits!

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

Start Your Search