Windward Cay Real Estate

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

Windward Cay features beautifully landscaped grounds and well-maintained homes that exude a sense of community and pride. The architectural styles vary, offering a delightful mix of contemporary and traditional designs, ensuring that there’s something for everyone. Residents here enjoy spacious living, with many properties boasting private backyards, perfect for family gatherings or quiet evenings under the stars.

One of the standout features of Windward Cay is its prime location. Just minutes away, you’ll find pristine beaches, world-class shopping, and an array of dining options that cater to every palate. The vibrant downtown Naples area is a short drive away, offering cultural attractions, art galleries, and lively events throughout the year.

For those who appreciate outdoor activities, Windward Cay is surrounded by lush parks and recreational facilities, making it easy to enjoy Florida's sunny weather. Whether you prefer golfing, biking, or simply taking a leisurely stroll, the options are endless.

In Windward Cay, you’re not just buying a home; you’re investing in a lifestyle. With its welcoming atmosphere, convenient amenities, and stunning natural surroundings, this subdivision truly embodies the best of Naples living. Come discover why Windward Cay is the perfect place to call 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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