Grayson Square Homes with Gated Amenities

Welcome to Grayson Square, a picturesque subdivision nestled in the heart of Winter Park, Florida. Known for its lush landscapes and inviting community spirit, Grayson Square offers a serene escape while remaining conveniently close to the vibrant amenities of the city. This charming neighborhood is located in Seminole County, where the sun shines bright and the lifestyle is nothing short of idyllic.

Grayson Square is not just a place to live; it's a lifestyle choice that emphasizes comfort, security, and community. The homes here are designed with modern elegance in mind, boasting spacious layouts and high-end finishes that cater to today’s discerning homeowner. Each residence is a testament to quality craftsmanship, with thoughtful details that make every house feel like a home.

One of the standout features of Grayson Square is its gated amenities, providing residents with an added layer of security and peace of mind. The community is enclosed, ensuring a safe environment for families and individuals alike. Enjoy leisurely strolls through beautifully landscaped paths, or gather with neighbors at the community clubhouse, where friendships are forged and memories are made.

In addition to the luxurious homes and gated security, Grayson Square is ideally situated near Winter Park's renowned shopping, dining, and recreational options. With easy access to parks, lakes, and cultural attractions, residents can enjoy a perfect blend of tranquility and excitement.

Discover the charm of Grayson Square and experience a community that feels like home, all while enjoying the best that Winter Park has to offer. Your dream home awaits!

Newest Grayson Square Homes with Gated Amenities

$399,995

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Talk about VALUE! Almost brand new and move in ready CORNER townhome in Winter Park! This beautiful 3 bedroom 2.5 bathroom home with just under 1,800 sq. ft. offers a large 2 car garage, light and bright living spaces, clean and modern designer features, and comes equipped with a full kitchen appliance package and washer/dryer. The first floor offers expansive living spaces with enough room for a dining area and family room. All of which flow seamlessly into the open kitchen. With white cabinets and Quartz counter tops, the kitchen is a show stopper! The entire first level is adorned with tile and offers a half bathroom and access to the covered back porch. Just up the stairs, you will find all of your bedrooms and full bathrooms. The primary bedroom and en suite bathroom are ample in size and also offer a large walk in closet. Both secondary bedrooms are down the hall and share a large full bathroom. The small gated community of townhomes offers a community pool and serene pond. HOA includes cable! Make sure to put this on your must see list!

2857 Clever Lane, Winter Park

$389,900

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

BUYER INCENTIVE! Nearly-New 2023 Pulte Townhome • 3BD/2.5BA + Garage • Quartz Counters • Rate Buydown Available Imagine owning a beautifully maintained, nearly-new Pulte townhome in the heart of Winter Park. Built in 2023 and still covered by the transferable Pulte 10-year structural warranty, this home offers modern design, energy efficiency, and peace of mind. The seller is offering a rate buydown incentive toward allowable closing costs or prepaid expenses with an acceptable offer—making this one of the most affordable opportunities in the community. Located in the gated community of Grayson Square, this stylish two-story residence features an attached one-car garage and an open-concept main living area perfect for entertaining. The kitchen showcases elegant Quartz countertops, Whirlpool stainless steel appliances, ample cabinetry, and a large island overlooking the living and dining spaces. Washer and dryer are included for added convenience. Enjoy upgraded smart-home technology and fiber-optic high-speed internet and cable, already included in the low HOA—ideal for working from home or seamless streaming. Upstairs, the spacious primary suite offers a generous walk-in closet and a private en-suite bath designed for comfort and relaxation. Two additional bedrooms provide flexible space for family, guests, or a dedicated home office. With no direct rear neighbors, the covered back patio offers peaceful outdoor views. The community is beautifully maintained and features a resort-style pool, cabana, and sidewalks perfect for evening strolls. Grayson Square also maintains escrow reserves for future roof replacement and exterior painting, adding to the low-maintenance lifestyle. This prime Winter Park location places you minutes from shopping, dining, gyms, entertainment, parks, and three local colleges, as well as top commuter routes like 417—giving you easy access to everything Central Florida has to offer while coming home to a quiet, friendly neighborhood. If you’re looking for a modern, energy-efficient home with premium finishes and virtually maintenance-free living, this is the one you’ve been waiting for.

2017 Canny Cove, Winter Park

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