Windward Cay Condos for Sale

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida. This charming subdivision offers an idyllic blend of tranquility and convenience, making it the perfect place to call home. Surrounded by lush landscapes and serene waterways, Windward Cay is designed for those who appreciate both the beauty of nature and the vibrancy of city life.

Located in Collier County, Windward Cay is just a short drive away from the stunning beaches of Naples, renowned for their powdery white sands and azure waters. Residents enjoy easy access to a variety of shopping, dining, and entertainment options, ensuring that everything you need is right at your fingertips. The community is also conveniently situated near top-rated schools and healthcare facilities, making it an ideal location for families and retirees alike.

Windward Cay features a selection of beautifully designed condos for sale, perfect for those seeking a low-maintenance lifestyle without compromising on comfort or style. These spacious units boast modern amenities, open floor plans, and inviting outdoor spaces, allowing residents to fully embrace the Florida lifestyle. Whether you’re sipping coffee on your private balcony or hosting friends for a sunset barbecue, these condos provide the perfect backdrop for making lasting memories.

With its prime location, friendly atmosphere, and stunning natural surroundings, Windward Cay is more than just a place to live—it’s a community where you can truly thrive. Explore the available condos for sale today and discover the exceptional lifestyle that awaits you in this enchanting Naples neighborhood!

Newest Windward Cay Condos for Sale

$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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