Windward Cay Real Estate

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida, within Collier County. This picturesque subdivision is a perfect blend of serene living and vibrant community, making it an ideal choice for families, retirees, and everyone in between.

Windward Cay boasts a collection of charming single-family homes, each designed to harmonize with the lush, tropical surroundings. The architecture reflects the quintessential Florida style, with inviting outdoor spaces that encourage relaxation and connection with nature. Many homes feature private pools, spacious patios, and beautifully landscaped yards, providing the perfect backdrop for both entertaining and peaceful solitude.

Residents of Windward Cay enjoy a wealth of amenities that enhance the quality of life. The community is conveniently located near some of Naples' finest shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. Additionally, the stunning Gulf Coast beaches are within easy reach, offering endless opportunities for sun-soaked days and breathtaking sunsets.

Nature enthusiasts will appreciate the nearby parks and recreational areas, where you can explore scenic walking trails, engage in outdoor sports, or simply bask in the beauty of Florida's diverse wildlife. The community is also known for its friendly atmosphere, making it easy to forge lasting connections with neighbors.

Whether you’re seeking a peaceful retreat or an active lifestyle, Windward Cay offers the best of both worlds. Experience the allure of Naples living—where every day feels like a vacation. Discover your new home in Windward Cay 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

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