Windward Square Sec 2 Homes with Tennis Court(s) Community Features

Welcome to Windward Square Sec 2, a hidden gem nestled in the heart of Winter Park, Florida, within the picturesque Seminole County. This charming subdivision is not just a collection of homes; it’s a vibrant community where neighbors become friends and families thrive.

Windward Square Sec 2 boasts a delightful array of homes, each thoughtfully designed to provide comfort and style. With lush landscaping and meticulously maintained properties, the neighborhood exudes an inviting atmosphere that is perfect for both relaxation and recreation. One of the standout features of this community is its access to tennis courts, catering to both seasoned players and those looking to pick up a racket for the first time. Whether you're practicing your serve or enjoying a friendly match with neighbors, the tennis courts are a fantastic way to stay active and socialize.

Beyond the courts, residents of Windward Square Sec 2 enjoy a plethora of community amenities, including scenic walking paths, playgrounds, and picnic areas—perfect for family gatherings or quiet evenings under the stars. The location is unbeatable, with Winter Park’s charming shops, exquisite dining options, and lush parks just a stone's throw away.

Discover the perfect blend of community spirit and modern living in Windward Square Sec 2. Whether you’re looking to buy your first home or seeking a serene retreat, this subdivision promises a lifestyle that is as enriching as it is enjoyable. Come and experience the warmth and camaraderie that make Windward Square Sec 2 truly special!

Newest Windward Square Sec 2 Homes with Tennis Court(s) Community Features

$255,000

2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 2 SubDv. ⋅ 32792 Zip Code

Virtually Staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and dining area, while sliding glass doors lead to a private, fenced backyard with a large concrete patio?perfect for morning coffee, weekend barbecues, or unwinding after a long day. With no rear neighbors and views of the community green space, you?ll enjoy added privacy and tranquility. The kitchen is designed for everyday ease, featuring ample cabinetry, a breakfast bar, and all appliances included, making move-in simple. Retreat to the oversized primary suite with a walk-in closet and direct patio access, creating a true indoor-outdoor flow. The second bedroom offers flexibility for guests, a home office, or creative space. Step outside your front door and enjoy resort-style amenities, including three swimming pools, tennis courts, a clubhouse, and a playground—all with low HOA fees. With parking for three vehicles, convenience is built right in. Located close to shopping, dining, major roadways, and just minutes from Winter Park’s Park Avenue, this home delivers both comfort and connection. Owner-occupant only community—ideal for those looking to put down roots and enjoy a true neighborhood feel. Live more. Maintain less. Welcome home.

2651 Cayman Way, Winter Park

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