Windward Square Sec 2 Real Estate

Welcome to Windward Square Sec 2, a hidden gem nestled in the heart of Winter Park, Florida, within the vibrant Seminole County. This charming subdivision offers a unique blend of suburban tranquility and urban convenience, making it an ideal destination for families, professionals, and retirees alike.

Windward Square Sec 2 is characterized by its picturesque tree-lined streets, meticulously maintained lawns, and a warm sense of community. The neighborhood boasts a variety of beautifully designed single-family homes, each reflecting the unique tastes of its residents while maintaining a cohesive aesthetic that enhances the overall appeal of the area. Whether you’re looking for a cozy starter home or a spacious residence for a growing family, Windward Square Sec 2 has something to suit every lifestyle.

One of the standout features of this subdivision is its proximity to Winter Park’s vibrant downtown area, renowned for its eclectic mix of shops, restaurants, and cultural attractions. Enjoy leisurely strolls along Park Avenue, where you can indulge in gourmet dining or explore local boutiques. For outdoor enthusiasts, the nearby parks and lakes offer ample opportunities for recreation, from biking and hiking to picnicking and fishing.

Families will appreciate the top-rated schools within the Seminole County School District, ensuring that children receive an excellent education. Additionally, the community fosters a friendly atmosphere, with regular neighborhood events and gatherings that encourage connections among residents.

Discover the charm and convenience of Windward Square Sec 2, where every day feels like a retreat in this idyllic Winter Park neighborhood. Come and experience the perfect blend of comfort and community!

Newest Listings in Windward Square Sec 2

$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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