Revolutionizing · Modernizing · SimplifyingRevolutionizing · Modernizing · Simplifying57 homes for sale, median asking price $1,245,000 - Winter Park is a buyer's market today. Calculated live, right now.
Over six months of supply means there are more homes for sale than the current pace of sales absorbs. Buyers have choice and time, and sellers usually have to compete on price or condition.
There are 57 homes for sale and 63 sold in the last twelve complete months, which is 10.9 months of supply. Homes that sold went for a median of 98% of their asking price after a median 130 days on the market.
Asking prices in Winter Park currently run from $355,000 to $4,250,000, on a median home of about 1,566 square feet with 3 bedrooms.
| Month | Homes sold | Median sold price | |
|---|---|---|---|
| Sep 2025 | 8 | $661,750 | |
| Oct 2025 | 7 | $1,075,000 | |
| Nov 2025 | 9 | $1,090,000 | |
| Dec 2025 | 2 | $730,300 | |
| Jan 2026 | 1 | $1,400,000 | |
| Feb 2026 | 5 | $1,900,000 | |
| Mar 2026 | 8 | $846,000 | |
| Apr 2026 | 3 | $1,441,661 | |
| May 2026 | 4 | $1,047,000 | |
| Jun 2026 | 4 | $1,569,400 | |
| Jul 2026 | 10 | $1,918,150 | |
| Aug 2026 | 2 | $575,000 |
See the Winter Park sales one by one - the most recent closings with what each home asked, what it got, and how many sellers beat their asking price.
| Price | For sale | Share | |
|---|---|---|---|
| $300k to $500k | 7 | 12% | |
| $500k to $750k | 15 | 26% | |
| $750k to $1M | 3 | 5% | |
| $1M to $1.5M | 12 | 21% | |
| $1.5M and up | 20 | 35% |
| Bedrooms | For sale | Median asking price |
|---|---|---|
| 1 bedroom | 9 | $549,000 |
| 2 bedrooms | 11 | $699,000 |
| 3 bedrooms | 19 | $1,449,322 |
| 4 bedrooms | 8 | $1,674,000 |
| 5 or more | 5 | $3,250,000 |
Each of these has its own guide with the same live numbers, plus what the area is actually like to live in.
Each of these is its own page, with the live figures for that search rather than just a list.
Winter Park sits in Grand County. See the whole Grand County report, or compare one of its other markets:
Or read the two markets side by side on one page:
There are 57 residential homes for sale in Winter Park right now, 12 of which came on the market in the last 30 days. Asking prices run from $355,000 to $4,250,000.
The median asking price is $1,245,000, about $829 per square foot. Homes that actually closed in the last twelve complete months sold for a median of $1,090,000 - roughly $742 per square foot.
Winter Park is a buyer's market: 10.9 months of supply, worked out from 57 homes for sale against 63 sales over the last twelve complete months. Over six months of supply means there are more homes for sale than the current pace of sales absorbs. Buyers have choice and time, and sellers usually have to compete on price or condition.
Homes on the market today have been listed a median of 76 days, and the ones that sold in the last twelve complete months took a median of 130 days from listing to closing. They sold for a median of 98% of their asking price.
63 homes closed in Winter Park over the last twelve complete calendar months, 15 of them in the last 90 days and 3 in the last 30. The month-by-month table on this page shows how that was spread across the year.
They are computed the moment you open this page, straight from the live MLS feed - not published once a month and left to go stale. Residential listings only; rentals, land, commercial and fractional co-ownership shares are excluded so they cannot distort the medians.
Every number on this page is recalculated from the live MLS feed at the moment the page loads - it is not a monthly snapshot. Homes for sale, prices and days on market are residential listings only; rentals, land and commercial are excluded, as are fractional co-ownership shares, which are priced per share and would distort the medians. Sold figures cover the last twelve complete calendar months. Market data is deemed reliable but not guaranteed - talk to us before making a decision on it.
The listings these figures are drawn from were last changed at the MLS on September 22, 2026 at 5:11 PM Mountain time. The figures themselves are worked out again from scratch every time this page is opened.
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