Grayson Square Homes with Pool Amenities

Welcome to Grayson Square, a charming subdivision nestled in the heart of Winter Park, Florida, within Seminole County. This picturesque community is renowned for its serene atmosphere, friendly neighbors, and an ideal blend of modern living and natural beauty. Grayson Square is perfectly positioned to offer residents easy access to the vibrant culture and amenities of Winter Park, making it a sought-after destination for families and professionals alike.

One of the standout features of Grayson Square is its stunning homes, many of which come complete with inviting pool amenities. Imagine stepping out into your backyard oasis, where you can unwind in your private pool, host summer barbecues, or simply soak up the Florida sun. These homes are designed with both comfort and style in mind, boasting spacious layouts, contemporary finishes, and lush landscaping that enhances the overall appeal of the neighborhood.

Living in Grayson Square means enjoying the best of both worlds: a peaceful retreat just moments away from the bustling downtown area of Winter Park. Residents can explore an array of boutique shops, delightful dining options, and cultural attractions, including the renowned Rollins College and the beautiful lakes that dot the landscape.

Whether you’re a first-time homebuyer or looking to upgrade your living situation, Grayson Square offers a unique blend of luxury and convenience. With its inviting community atmosphere and homes equipped with pool amenities, it’s the perfect place to create lasting memories. Discover your dream home in Grayson Square and experience the enchanting lifestyle that awaits you in Winter Park!

Newest Grayson Square Homes with Pool 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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