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 3 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 August 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
$405,500Median sale price
$212.64Median per square foot
86 daysMedian days to contract
3Homes sold in 12 months
Sale prices ran from $399,000 to $410,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
By size
| Home size | Sales | Median price | Median $/sq ft | Median days |
|---|
| Under 2,000 sq ft | 3 | $405,500 | $212.64 | 86 days |
Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Never reduced 1 sales, closed at 100.0% of asking8 days
Reduced at least once 2 sales, closed at 98.5% of the reduced price98 days
Sellers who priced correctly and held their number went under contract in a median 8 days. Sellers who had to reduce took 98 days and still closed at 98.5% of their already reduced price, after a typical cut of $46,000. Opening high costs time and money, in that order.
How buyers paid
Cash 2 sales67%
FHA 1 sales33%
Cash was 67% 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.
What is around Grayson Square
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.
| Driving to | Time | Miles |
|---|
| Downtown Orlando | 25 min | 11.3 |
| Orlando International Airport | 29 min | 22.9 |
| Winter Park | 14 min | 5.2 |
| Heathrow and Lake Mary offices | 31 min | 15.7 |
Schools nearby- The Lyman School 0.4 mi
- Chesterton Academy of Orlando 0.7 mi
- Highlands Latin School 0.7 mi
- Eastbrook Elementary School 0.9 mi
Parks and recreation- Branch Tree Park 1.0 mi
- Winter Park Estates Park 1.4 mi
- Phelps Park 1.6 mi
- Goldenrod Park 1.7 mi
Groceries and errands- In-N-Out Market 0.3 mi
- SuperFresh Market 0.5 mi
- Lacomka Bakery & Russian Store, Orlando FL 0.7 mi
- Publix Super Market at Casselberry Commons 0.8 mi
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 31 August 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
Homes for sale in Grayson Square right now
Current listings appear below and update automatically as homes come on and off the market. If nothing is showing, there is nothing available in Grayson Square today, which happens in a neighborhood this size.
About this data. Source is the Stellar MLS feed for Grayson Square in Winter Park, Seminole County, covering closed sales from 5 September 2025 through 31 August 2026, refreshed monthly and current as of August 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. 0 records were excluded as off-market transfers rather than open market sales. Condition is inferred from listing descriptions. Data believed accurate but not guaranteed; listings and closings change daily.
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.
