Winter Park Market Report
Winter Park, FL Home Prices, August 2026, Median $624,900
Median Sale Price
$624,900
-3.12% vs prior month
Price / Sq Ft
$339
rank 1 of 10 markets
Months of Supply
3.90
Balanced Market
Active Listings
235
Single-family, 32789
Median Days on Market
16
rank 9 of 10 markets
List Price vs. Sold Price %
98.2%
Of final asking price, August 2026
3-Month Average
$633,300
up 10.91% vs same 3 months last year
Absorption Rate
~60
Sales per month, derived
Key takeaways
- The Winter Park median single-family sale price was $624,900 in August 2026, down 3.12% from the prior month.
- Winter Park is classified as a balanced market at 3.90 months of supply.
- Median price per square foot was $339, the number 1 of the ten markets we track.
- Median days on market was 16, against a ten-market median near 21.5, at 98.2% of last list price.
- The three month average median was $633,300, up 10.91% against the same three months a year earlier.
The median single-family sale price in Winter Park, Florida was $624,900 in August 2026, down 3.12% from the prior month. Homes carried a median of 16 days on market at $339 per square foot, with 235 active listings and 3.90 months of supply, placing Winter Park in balanced territory.
What is the median home price in Winter Park, FL?
The August 2026 median sale price for a single-family home in Winter Park was $624,900. Among the ten Central Florida markets we track, Winter Park ranks number 6 by median sale price, roughly 4% below Lake Mary at $650,000 and about 1% above Maitland at $620,000.
A single month of closings is a small sample in most of these markets, so we lead with a three month average rather than a month-over-month change. Across June, July and August the Winter Park median averaged $633,300, up 10.91% against the same three months a year earlier. That window smooths the mix of what happened to close and matches the season, which a comparison against last month cannot do.
Median price per square foot was $339. Taken against the median sale price, that implies a typical Winter Park transaction of roughly 1,843 square feet. That is a derived figure rather than a reported one, and it is useful mainly as a sanity check on what the inventory in the City of Winter Park actually consists of.
One caution on reading a single month. Medians move with the mix of what closed, not only with underlying value. A month in which a handful of higher-priced or lower-priced homes close can shift the median without anything changing for a specific property. Treat the direction across three months as the signal and any single month as noise.
Is Winter Park a buyer's or seller's market?
Winter Park is currently classified as a balanced market, on 3.90 months of supply. We classify on months of supply: under three months is a seller's market, three to six is balanced, and over six favors buyers. Those thresholds are ours, not the data source's, and we state them so you can judge the label rather than take it on faith.
Across the ten markets we track: 3 seller's markets, 7 balanced markets. Winter Park sits at 3.90 months, near the middle of the ten.
With 235 active listings against 3.90 months of supply, Winter Park is absorbing on the order of 60 sales per month. For a seller, that absorption number often matters more than the median, because it describes how much company a listing has rather than what the market did last month.
How Winter Park compares to the other nine markets
| Market | Median | MoM | $/Sq Ft | Days | Supply |
|---|---|---|---|---|---|
| Dr. Phillips | $962,000 | +60.33% | $312 | 56 | 3.80 |
| Windermere | $960,000 | -17.06% | $325 | 75 | 4.50 |
| Lake Nona | $832,250 | +2.75% | $287 | 69 | 5.10 |
| Winter Garden | $670,066 | -10.06% | $255 | 22 | 3.70 |
| Lake Mary | $650,000 | +2.77% | $270 | 20 | 3.00 |
| Winter Park | $624,900 | -3.12% | $339 | 16 | 3.90 |
| Maitland | $620,000 | -9.16% | $283 | 19 | 2.70 |
| Oviedo | $581,500 | -3.08% | $262 | 21 | 2.60 |
| Longwood | $569,250 | +9.47% | $256 | 12 | 2.50 |
| Orlando | $425,000 | -4.49% | $244 | 26 | 4.00 |
Price per square foot and median sale price do not always move together, and the gap between them is usually a lot-size and product story rather than a value story. A market with smaller, older homes on smaller lots can carry a higher per-square-foot figure than a market with a much higher median, simply because the homes are smaller. Read the two columns together rather than either alone.
How long homes are taking to sell
Median days on market for Winter Park was 16 in August 2026, against a ten-market median near 21.5. Sellers received a median of 98.2% of their last list price.
This is median cumulative days on market straight from Stellar MLS, so it counts the days a listing sat before going under contract rather than an estimate. Read it next to percent of last list price. A market that sells quickly and close to ask is tight; one that sells quickly only after reductions is not, and the two numbers together tell you which you are looking at.
What this means if you are selling
With 235 active listings and 3.90 months of supply, the pricing decision carries real weight. At roughly 60 absorptions a month against that inventory, a Winter Park listing is not scarce simply by virtue of its address.
The practical consequence is that the first two weeks of exposure do most of the work. An aspirationally priced listing rarely gets corrected by a competing offer; it accumulates days and invites a reduction. If you are weighing a number, our seller net proceeds calculator shows what a given sale price actually returns after commission and closing costs, and you can request an address-level valuation rather than working from a market-wide median.
What this means if you are buying
Supply sits near the middle of the region, which makes timing matter more than leverage. 235 active listings and 16 median days on market describe the market as a whole, not any particular street.
Submarkets inside Winter Park behave differently from the aggregate. Waterfront, gated, and golf-adjacent inventory can stay tight while a broader median softens, and the reverse happens too. A market-level supply figure will not tell you what is happening on a specific block. Browse current Winter Park listings for what is actually available, and if you are relocating for a clinical role, our physician relocation guide covers the financing and timing specific to that move.
Frequently asked questions
What is the median home price in Winter Park, FL?
The median single-family sale price in Winter Park was $624,900 in August 2026, down 3.12% from the prior month. This covers single-family residences within the City of Winter Park and comes from Stellar MLS.
Is Winter Park a buyer's or seller's market in 2026?
Winter Park is classified as a balanced market as of August 2026, with 3.90 months of supply and 235 active single-family listings. We classify on months of supply: under three months is a seller's market, three to six is balanced, and over six favors buyers. Those thresholds are ours, not the data source's, and we state them so you can judge the label rather than take it on faith.
How much does a home cost per square foot in Winter Park?
The median price per square foot in Winter Park was $339 in August 2026. That is the number 1 among the ten Central Florida markets we track.
How long does it take to sell a home in Winter Park?
Half of the homes that closed in August 2026 went under contract within 16 days of listing, against a ten-market median near 21.5 days. Sellers received a median of 98.2% of their last list price.
How many homes are for sale in Winter Park?
There were 235 active single-family listings in Winter Park as of August 2026, representing 3.90 months of supply at the current absorption rate of roughly 60 sales per month.
Source: Stellar MLS InfoSparks, Single Family Residence, City of Winter Park, data through August 2026. Compiled by Sean Spencer and Barbara Vance, Premier Sotheby's International Realty. Medians reflect all single-family price points within the geography. Based on information from the Stellar Multiple Listing Service for the period September 2025 through August 2026. This information may or may not include all listed expired, withdrawn, pending or sold properties of one or more members of the Stellar Multiple Listing Service. Market data changes monthly; contact us for a current address-level analysis.