Windward Cay Real Estate

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida. This picturesque subdivision, located in Collier County, offers a serene blend of natural beauty and modern conveniences, making it an ideal destination for families, retirees, and anyone seeking a tranquil lifestyle.

Windward Cay is characterized by its charming, well-maintained homes that reflect a variety of architectural styles, providing a unique character to the community. Lush landscaping, palm trees swaying in the gentle Florida breeze, and scenic waterways create a picturesque backdrop for everyday living. Residents can enjoy leisurely strolls through the neighborhood or take advantage of the nearby parks and recreational areas.

One of the standout features of Windward Cay is its proximity to Naples’ pristine beaches. Just a short drive away, you can sink your toes into the soft, white sands of the Gulf Coast, where breathtaking sunsets and vibrant sunsets await. The area is also known for its world-class dining, shopping, and cultural attractions, including art galleries and theaters that showcase the local talent.

For outdoor enthusiasts, Windward Cay offers easy access to numerous golf courses, nature trails, and water activities, ensuring there’s always something to do. Families will appreciate the highly-rated schools and community events that foster a sense of belonging.

Whether you’re looking for a peaceful retreat or an active lifestyle, Windward Cay in Naples, FL, offers the perfect blend of comfort, community, and coastal charm. Discover your dream home in this idyllic subdivision today!

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

Start Your Search