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 an idyllic blend of tranquility and convenience, making it the perfect place to call home. Windward Cay is renowned for its lush landscapes, serene lakes, and beautifully designed homes that cater to a variety of lifestyles.

As you stroll through the tree-lined streets of Windward Cay, you’ll be captivated by the stunning architecture and well-maintained properties that reflect the vibrant spirit of Southwest Florida. The community is thoughtfully planned, offering a mix of single-family homes and villas, each with unique features and finishes. Whether you’re seeking a cozy retreat or a spacious family residence, Windward Cay has something to suit every taste.

One of the standout features of this subdivision is its proximity to Naples' world-class amenities. Residents enjoy easy access to pristine beaches, upscale shopping, and gourmet dining options, all just a short drive away. For outdoor enthusiasts, the nearby parks and golf courses provide ample opportunities for recreation and relaxation. Plus, the community’s close-knit atmosphere fosters a sense of belonging, making it easy to connect with neighbors and create lasting friendships.

In Windward Cay, you’re not just buying a home; you’re investing in a lifestyle filled with sunshine, beauty, and community spirit. Experience the charm of Naples living in this delightful subdivision, where every day feels like a vacation. Come discover your dream home in Windward Cay today!

Newest Listings in Windward Cay

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windward Cay BLDG.

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 DR Unit 622, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS ⋅ Windward Cay BLDG.

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 DR Unit 612, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.