Grayson Square is a 2020s neighborhood in Winter Park, in the 32792 zip code. Homes are wood frame and hardiplank type. Most homes fall between about 1,800 and 1,900 square feet under air, the median lot is about 0.04 acres, and a one car garage is standard.
Homes here carry an HOA, billed monthly, typically around $275. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Essentially all built in the 2020s.
Construction Wood frame and hardiplank type. Shingle roofs are near universal.
Style Craftsman, Coastal, Florida. Predominantly two story.
Size Most homes fall between about 1,800 and 1,900 square feet under air.
Bedrooms Three bedrooms is the most common plan.
Garage A one car garage is standard.
Lot The median lot is about 0.04 acres.
HOA Billed monthly, typically around $275. Confirm on a specific parcel before relying on it.
Where Grayson Square is
Grayson Square, centered at 28.621434, -81.308159. Drag to explore.Street level, inside the neighborhood. Drag to look around.
Drive times below are measured on the road network from the center of Grayson Square, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
Nearest is not the same as zoned. The schools above are the closest ones to Grayson Square by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Seminole County Public Schools before it matters to a decision.
Places and drive times from Google, checked 9 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Grayson Square actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 2 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated October 2026.
Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.
What homes sold for in Grayson Square
$402,250Median sale price
$211Median per square foot
58 daysMedian days to contract
2Homes sold in 12 months
Sale prices ran from $399,000 to $405,500.
Price cuts and time to contract
Median days to go under contract. Shorter is better.
Never reduced 1 sale, closed at 100% of asking8 days
Reduced at least once 1 sale, closed at 101.6% of the reduced price108 days
Sellers who held their number went under contract in a median 8 days. Sellers who had to reduce took 108 days and closed at 101.6% of their already reduced price, after a typical cut of $37,000.
How buyers paid
FHA 1 sale50%
Cash 1 sale50%
Cash was 50% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.
Questions about a specific home in Grayson Square, or want to know what yours would sell for? Call or text Brenden Rendo at 407-616-9019 or send a message.
About this data. Source is the Stellar MLS feed for Grayson Square in Winter Park, Seminole County, covering closed sales from 13 October 2025 through 8 October 2026, refreshed monthly and current as of October 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.
