grayson square
Homes for Sale in Winter Park, FL
True comps, carrying-cost math, and listings before the portals.
grayson square right now
🔴 Off the recent peak. The trailing-12-month median ($408K) is down 10.8% from the prior 12 months ($457K). With about a dozen sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending July 13. Confidence: Low (4 and 9 sales in the two windows).
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Updated July 13, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
grayson square market snapshot (as of July 13, 2026): the median sale price is about $408K ($214 per sq ft over the trailing 12 months of closed sales), and a median 87 days on market for closed sales. The trailing-12-month median is down 11% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
grayson square is a community of 129 homes in Winter Park, Seminole County, built between 2023 and 2024 (median 2023), with a median living area of about 1,907 square feet. 30% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of grayson square. Swipe to explore the community.
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grayson squarePrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 13 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($408K) IS the median in the snapshot above, and the move from 2025 ($457K) IS the -10.8% one-year change.
Windows contain 0 to 51 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Deemed reliable but not guaranteed.
Grayson Square Market Scorecard
Grayson Square is currently a thin data. 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.
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.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in grayson square buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (3.8). Basis: Recent Direction -10.8% year-over-year; Owner Commitment 30% owner-occupied; Pricing Power 92.7% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA - confirm current dues
- 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 homes for sale in grayson square on the map →
Frequently Asked Questions
What is the median home price in grayson square?
How long do homes in grayson square take to sell?
How many homes are in grayson square?
What share of grayson square is owner-occupied?
When were the homes in grayson square built?
Do cash buyers compete in grayson square?
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?
Nearby Communities
Explore more neighborhoods near grayson square with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: July 11, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| 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 your area comps.
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