Windward Cay Real Estate

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

Windward Cay is renowned for its picturesque surroundings, featuring lush landscaping and serene water views that create a peaceful atmosphere. The community is thoughtfully designed with a variety of single-family homes, each exuding unique character and charm. Whether you’re looking for a cozy retreat or a spacious family abode, Windward Cay has something to suit every taste and lifestyle.

One of the standout features of this subdivision is its prime location. Residents enjoy easy access to Naples' stunning beaches, upscale shopping, and gourmet dining options, all just a short drive away. The nearby Delnor-Wiggins Pass State Park and Clam Pass Park offer endless opportunities for outdoor recreation, from sunbathing to kayaking, making it a haven for nature lovers.

Moreover, Windward Cay boasts a strong sense of community, where neighbors become friends and gatherings are common. With well-maintained common areas and walking paths, you’ll find plenty of opportunities to socialize and enjoy the beautiful Florida weather.

In Windward Cay, you’re not just buying a home; you’re investing in a lifestyle filled with warmth, community spirit, and endless sunshine. Experience the best of Naples living in this delightful subdivision—your dream home awaits!

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