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 only known for its serene atmosphere but also for its vibrant community spirit, making it an ideal place for families and individuals alike.

Windward Square Sec 2 boasts a unique blend of modern amenities and natural beauty, offering residents a tranquil retreat just moments away from the bustling city life. The community features beautifully designed homes, many of which come equipped with private tennis courts, perfect for both seasoned players and casual enthusiasts. Imagine stepping out of your back door onto your very own court, ready to enjoy a friendly match or perfect your serve under the warm Florida sun.

In addition to the tennis courts, Windward Square Sec 2 is surrounded by lush landscaping and well-maintained common areas, providing ample opportunities for outdoor activities and relaxation. The neighborhood is designed with walkability in mind, encouraging residents to explore the scenic surroundings and engage with their neighbors.

Winter Park is renowned for its rich cultural scene, including art galleries, boutique shops, and exquisite dining options. Residents of Windward Square Sec 2 enjoy easy access to these attractions while still relishing the peaceful ambiance of their community.

Whether you’re seeking an active lifestyle or a serene place to call home, Windward Square Sec 2 offers the perfect blend of both. Come discover the charm and amenities that await you in this delightful Winter Park neighborhood!

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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