Grayson Square Homes with Gated Amenities

Welcome to Grayson Square, a hidden gem nestled in the heart of Winter Park, Florida. This exquisite subdivision offers a unique blend of luxury, comfort, and community living, making it the perfect place to call home. Located in Seminole County, Grayson Square boasts a prime location that combines the tranquility of suburban life with the vibrant culture of Winter Park.

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 entrance welcomes you into a beautifully landscaped community where safety and privacy are prioritized. As you stroll through the neighborhood, you’ll be captivated by the stunning architecture of the homes, each designed with modern elegance and thoughtful details.

The homes in Grayson Square are perfect for families and professionals alike, offering spacious floor plans, gourmet kitchens, and luxurious finishes. Many residences feature private backyards, ideal for entertaining or enjoying a quiet evening under the stars. The community is also designed with connectivity in mind, featuring walking trails and green spaces that encourage outdoor activities and foster neighborly interactions.

Living in Grayson Square means you are just moments away from Winter Park’s charming boutiques, gourmet dining, and cultural attractions. Whether you’re exploring the scenic lakes, enjoying local art festivals, or indulging in a day of shopping, everything you need is right at your fingertips.

Discover the allure of Grayson Square, where a vibrant community meets the serenity of gated living in one of Florida's most desirable cities. 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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