Windward Square Sec 2 Real Estate

Welcome to Windward Square Sec 2, a hidden gem nestled in the heart of Winter Park, Florida. This charming subdivision offers a perfect blend of suburban tranquility and vibrant community life, making it an ideal choice for families, retirees, and young professionals alike.

Windward Square Sec 2 is characterized by its beautifully landscaped streets and well-maintained homes, each exuding a unique charm that reflects the warmth of the community. Residents enjoy a peaceful atmosphere, complemented by the lush greenery and scenic views that define this enchanting neighborhood. With a variety of architectural styles, from modern designs to classic Floridian aesthetics, there’s a home to suit every taste.

One of the standout features of Windward Square Sec 2 is its proximity to Winter Park’s renowned amenities. Just a short drive away, you’ll find a plethora of shopping, dining, and entertainment options, including the upscale boutiques along Park Avenue and the delightful cafes that line the streets. For outdoor enthusiasts, the area boasts numerous parks and recreational facilities, providing ample opportunities for hiking, biking, and enjoying Florida’s beautiful weather.

Families will appreciate the highly-rated schools nearby, ensuring that children receive an excellent education. Additionally, the sense of community is palpable, with neighborhood events and gatherings that foster connections among residents.

Whether you’re looking to settle down or invest in a property, Windward Square Sec 2 offers a lifestyle that embodies the best of Winter Park living. Discover your dream home in this delightful subdivision and experience the charm and convenience that Windward Square Sec 2 has to offer!

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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