Grayson Square Real Estate

Grayson Square Real Estate

Welcome to Grayson Square, a charming subdivision nestled in the heart of Winter Park, Seminole County, Florida. This idyllic community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place to call home.

Grayson Square is known for its well-designed homes, beautiful landscaping, and a strong sense of community. The neighborhood features a variety of architectural styles, including traditional and contemporary designs, ensuring there is something to suit every taste and preference.

Residents of Grayson Square enjoy a range of amenities within close proximity. The neighborhood boasts well-maintained parks, playgrounds, and walking trails, providing ample opportunities for outdoor recreation and relaxation. The community also benefits from easy access to top-rated schools, shopping centers, dining options, and entertainment venues, ensuring that all your needs are catered to.

Winter Park, the city in which Grayson Square is located, is renowned for its vibrant cultural scene, upscale boutiques, and art galleries. Residents can explore the charming cobblestone streets of Park Avenue, indulge in gourmet dining experiences, or take a leisurely boat ride on the picturesque Winter Park Chain of Lakes.

With its prime location in Seminole County, Grayson Square offers a peaceful suburban lifestyle while being just a short drive away from downtown Orlando and its world-famous attractions. Whether you're a young professional, a growing family, or a retiree looking for a serene retreat, Grayson Square has something for everyone.

Come and discover the beauty and convenience of Grayson Square. It's more than just a neighborhood; it's a place to create lasting memories and call home.

Newest Listings in Grayson Square

$409,900
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
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
$389,000
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

2033 Canny Cove, Winter Park
$405,000
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Welcome to Grayson Square at Winter Park by Pulte Homes. This Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathrooms, a powder room, single-car garage, a covered rear lanai, washer, dryer, refrigerator, and window blinds. The spacious first floor with over 9' ceilings is ideal for entertaining, featuring an open concept gathering room, cafe and kitchen equipped with bright white cabinetry, a white ceramic subway tile backsplash, Lyra quartz countertops, and durable ceramic tile flooring, a pantry, and powder room. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and ensuite bathroom with double sink, quartz-topped vanity, linen closet, a private water closet and walk-in glass framed shower. Offering privacy and space for everyone, two additional bedrooms, the secondary bathroom and laundry are also on the second floor. Professionally curated design selections for this popular Springdale II townhome include designer cabinets with crown molding, quartz countertops, oversized ceramic tile flooring covering the first floor living areas and bathrooms, a washer, dryer, refrigerator, and blinds, soft, stain-resistant Shaw carpet in the bedrooms and second floor living areas and so much more! Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off of Howell Branch Road! Grayson Square is a low-maintenance neighborhood with gated access, a pond, no rear neighbors, a resort-style community pool with cabana,1GM high-speed fiber optic internet, along with 75 streaming cable and music channels, ground maintenance - all with no CDD. Boasting an unbeatable location in coveted Winter Park, just one mile from 436, 434, and less than 3 miles from 417, your like-new home at Grayson Square offers all of your daily conveniences, such as Starbucks and Publix, just minutes away! Plus, you'll have access to quality County and private schools. When it's time for a change of pace, you'll love your proximity to the famous shopping and dining of Park Avenue. Make Grayson Square at Winter Park your new address today!

1995 Canny Cove, Winter Park
Start Your Search