Grayson Square
Homes for Sale in Winter Park, FL
All 364 homes for sale in Winter Park, FL · median $684,500 · 121 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 $449,000, 33 median days on market, with 128 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).
| Location | Winter Park, Seminole County, FL · ZIP 32792 |
|---|---|
| Homes in the community | 141 (FL DOR 2025 assessment roll) |
| Years built | 2023–2024 (median 2023.0) |
| Typical living area | 1,907 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 30% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2023 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “grayson square key facts,” movewithmomentum.com/neighborhoods/grayson-square-winter-park, data as of September 20, 2026.
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, 151 homes are on the market and 19% are under contract — a steady corner of Winter Park.
Across Seminole County, 1,676 homes are active and 570 pending (25% under contract).
ZIP and county figures describe the wider market, not Grayson Square specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in grayson square, Winter Park
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
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.
A closer look at the Grayson Square market
The housing stock is 141 homes built between 2023 and 2024, and 30% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
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.
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Frequently Asked Questions
How many homes are in Grayson Square?
What share of Grayson Square is owner-occupied?
When were the homes in Grayson Square built?
Who is the best real estate agent for Grayson Square?
How do I find a top Winter Park real estate agent who knows Grayson Square?
Can Momentum Realty connect me with an agent for Grayson Square?
Where is Grayson Square, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 26, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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.
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Nearby Communities
Explore more neighborhoods near Grayson Square with Momentum Realty’s local guides.