Grayson Square Real Estate

Welcome to Grayson Square, an enchanting subdivision nestled in the heart of Winter Park, Florida, within the serene Seminole County. This charming community offers a perfect blend of modern living and natural beauty, making it an ideal choice for families, professionals, and retirees alike.

Grayson Square is characterized by its meticulously designed homes that showcase contemporary architecture, spacious layouts, and lush landscaping. Each property reflects a commitment to quality and style, providing residents with comfortable living spaces that are perfect for both relaxation and entertaining. With an array of floor plans available, there’s a perfect fit for everyone, whether you’re seeking a cozy retreat or a larger family home.

The community boasts an array of amenities designed to enhance your lifestyle. Residents can enjoy scenic walking trails, well-maintained parks, and inviting green spaces that encourage outdoor activities and foster a sense of community. Additionally, the proximity to Winter Park’s vibrant downtown area means you’re just minutes away from an array of dining, shopping, and cultural experiences, including art galleries and local festivals.

Families will appreciate the highly-rated schools located nearby, ensuring that children receive a top-notch education within a supportive environment. With easy access to major highways, commuting to nearby cities and attractions is a breeze, making Grayson Square an ideal location for those who work in the greater Orlando area.

Discover the charm and convenience of Grayson Square, where community spirit meets modern living in the picturesque setting of Winter Park, Florida. Your dream home awaits!

Newest Listings in Grayson Square

$399,000

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv.

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

$425,000

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv.

Welcome to Grayson Square at Winter Park by Pulte Homes. This interior 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 a pantry, bright white cabinetry, white subway ceramic tile backsplash, Lyra quartz countertops, and durable ceramic tile flooring, and a 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 Seminole County 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