Grayson Square Homes with Gated Amenities

Welcome to Grayson Square, an exquisite subdivision nestled in the heart of Winter Park, Florida, within the scenic Seminole County. This charming community offers a perfect blend of luxury, comfort, and security, making it an ideal choice for families and individuals seeking a serene lifestyle.

Grayson Square is renowned for its beautifully designed homes, each thoughtfully crafted to cater to modern living. With a variety of floor plans and architectural styles, prospective homeowners can find the perfect fit for their needs. The homes boast spacious interiors, high-end finishes, and ample outdoor spaces, ideal for entertaining or simply enjoying the Florida sunshine.

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 gated community ensures a safe environment for families, allowing children to play freely and neighbors to forge lasting friendships. In addition to the security, residents can enjoy a range of community amenities, including beautifully landscaped common areas, walking trails, and recreational facilities that foster a sense of community and well-being.

Located just minutes from Winter Park’s vibrant downtown, Grayson Square offers easy access to a variety of shopping, dining, and entertainment options. The area is also known for its top-rated schools, making it a perfect choice for families.

Discover the charm and elegance of Grayson Square, where a luxurious lifestyle awaits you in one of Florida’s most desirable communities. Embrace the opportunity to call this enchanting neighborhood your home!

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

$379,999

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

Huge Price Improvement!!Nearly-New 2023 Pulte Townhome • 3BD/2.5BA + Garage • Quartz Counters • 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. 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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