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

Welcome to Windward Square Sec 2, a picturesque subdivision nestled in the heart of Winter Park, Florida, within the beautiful Seminole County. This charming community offers a harmonious blend of serene living and vibrant recreational opportunities, making it an ideal place for families, retirees, and everyone in between.

Windward Square Sec 2 is renowned for its stunning homes, many of which come equipped with private tennis courts, catering to both tennis enthusiasts and those who appreciate an active lifestyle. Imagine stepping out into your backyard for a quick match or enjoying leisurely afternoons with friends and family, all while surrounded by lush landscaping and the warm Florida sun.

The community boasts well-maintained streets and a friendly atmosphere, where neighbors become friends and community events foster a sense of belonging. With a variety of home styles to choose from, prospective buyers will find options that suit their tastes and needs, whether it's a cozy family home or a spacious property perfect for entertaining.

Beyond the tennis courts, Windward Square Sec 2 is conveniently located near Winter Park's vibrant downtown area, filled with charming boutiques, delicious dining options, and cultural attractions. Residents can enjoy easy access to parks, lakes, and nature trails, ensuring that outdoor enthusiasts have plenty of opportunities to explore and unwind.

In Windward Square Sec 2, you'll find not just a home, but a lifestyle that embraces both relaxation and recreation. Come discover the allure of this exceptional community and make it your own!

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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