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 vibrant community living, making it an ideal choice for families, retirees, and everyone in between.

Windward Cay is renowned for its picturesque surroundings, boasting lush landscapes and serene waterways that create a peaceful atmosphere. With well-maintained homes and manicured lawns, the neighborhood exudes an inviting charm that welcomes residents and visitors alike. Whether you're enjoying a morning stroll or relaxing on your porch, the beauty of nature is always at your fingertips.

Conveniently located in Collier County, Windward Cay places you just minutes away from Naples' stunning beaches, upscale shopping, and gourmet dining. Explore the nearby Fifth Avenue South, where boutique shops and delightful eateries await. For outdoor enthusiasts, the area offers an abundance of recreational activities, including golf courses, parks, and nature preserves, ensuring that there's something for everyone to enjoy.

Families will appreciate the highly-rated schools in the area, providing excellent educational opportunities for children of all ages. The sense of community in Windward Cay is palpable, with friendly neighbors and organized events that foster connections and create lasting memories.

Whether you're seeking a permanent residence or a vacation home, Windward Cay is a delightful choice that promises a relaxed lifestyle in one of Florida's most desirable cities. Discover the charm and beauty of Windward Cay today, and make your dream of living in Naples a reality!

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.