Grayson Square
Homes for Sale in Winter Park, FL
All 337 homes for sale in Winter Park, FL · median $664,900 · 70 homes for sale in 32792 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
Nearby homes for sale
No active listings inside grayson square right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
As of September 2026, the MLS records 64 closed sales in grayson square in Winter Park, FL since 2023, the most recent in June 2026. Recorded prices since 2024 ran from $399,000 to $479,000 (median $451,090), on homes of 1,782 to 1,907 sq ft. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $459,450, 34 median days on market, with 124 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $6,850 ($6,250 with the full homestead exemption).
The market around Grayson Square
Grayson Square is too small for its own price trend, so here is the market around it.
In ZIP 32792, 137 homes are on the market and 21% are under contract — a steady corner of Winter Park.
Across Seminole County, 1,646 homes are active and 585 pending (26% under contract).
ZIP and county figures describe the wider market, not Grayson Square specifically. Momentum Research analysis of MLS records.
The Grayson Square buying strategy.
If we were buying in Grayson Square today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Grayson Square.
The location and the amenities are priced into every listing in Grayson Square. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Grayson Square buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Grayson Square sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Grayson Square, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Grayson Square home worth?
Get a no-obligation home value based on real comparable sales in Grayson Square, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Park →
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2023 (64 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how grayson square fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Grayson Square
Where is Grayson Square?
Grayson Square is a community in Winter Park, Seminole County, Florida, ZIP 32792.
Are there homes for sale in Grayson Square right now?
No active listings inside Grayson Square at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Grayson Square have an HOA or CDD?
No HOA is on record for Grayson Square in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Grayson Square with Momentum Realty’s local guides.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Grayson Square Market Scorecard
Grayson Square is currently a thin data market. Limited supply, a median asking price of n/a.
Go deeper: true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.