Burks Market Intelligence · October 2026
Winter Park real estate market report, October 2026
Prices are up, sales are up, and most homes still close below their asking price. Here are the latest readings for Winter Park, Florida, each with its source and its date, and what they mean for a seller, a buyer and a builder.
Key takeaways
Prices rose. Redfin's median sale price for the three months ending August 2026 was $865,000, up 11.6% from a year earlier.
More homes sold. 161 homes sold in August 2026, against 143 in August 2025.
Buyers still negotiate. Zillow found 67.3% of July sales closed below their final list price, and Redfin found 36.4% of listings took a price drop.
Good homes move fast. Zillow's median time to a pending contract was 22 days in August, down from 26 in June.
New construction sets the top. Completed new construction luxury sales cleared at $642 to $726 per square foot in our August 2026 review of Stellar MLS records.
Prices
Are Winter Park home prices going up?
Yes, on closed sales. Redfin reports a median sale price of $865,000 for the three months ending August 2026, up 11.6% from the same period a year earlier. The median sale price per square foot was $425, up 4.4%.
Zillow's typical home value for Winter Park was $464,563 as of August 31, 2026, up 1.5% over the year. That number looks like it disagrees with Redfin. It does not. Zillow models the value of every home in the area, sold or not. Redfin reports the middle price of the homes that actually sold. When more expensive homes make up more of the sales, the Redfin median rises faster than the typical value.
| Measure | Latest reading | What it tells you |
|---|---|---|
| Redfin median sale price | $865,000, up 11.6% | The middle price of homes that sold in the three months ending August 2026. |
| Redfin median price per square foot | $425, up 4.4% | A better guide than the median when the mix of homes changes. |
| Zillow typical home value | $464,563, up 1.5% | The modeled value of the typical home across the area, as of August 31, 2026. |
| Zillow median list price | $502,833 | What sellers were asking at the end of August 2026. |
Never blend these into one Winter Park price. Each measure covers a different set of homes, a different period and a different method.
Speed
How fast are homes selling in Winter Park?
It depends on which clock you read. Zillow's median time from listing to a pending contract was 22 days in August 2026, down from 25 in July and 26 in June. Redfin's median days on market was 46 in August, up from 35 a year earlier. Redfin also notes that the hottest homes go pending in about 23 days, while the average home takes about 54.
Read together: correctly priced homes find a buyer in three to four weeks. Homes that miss their price sit, and they pull the average up.
Negotiation
How much room is there to negotiate?
Some, on most homes. Redfin's sale to list ratio for August 2026 was 96.4%, and it describes the average home as selling about 4% below list. Only 11.2% of homes sold above their list price. Zillow's median sale to list ratio for July 2026 was 0.981, with 67.3% of sales closing below list and 14.9% closing above.
One more number matters to sellers. Redfin found 36.4% of listings took a price drop. That is 4.8 points lower than a year earlier, so sellers are pricing closer to the market than they were, but more than a third still start too high.
Supply
How many homes are for sale in Winter Park?
Zillow counted 377 homes for sale at the end of August 2026, with about 105 new listings that month. Redfin counted 161 closed sales in August, up 12.6% from 143 a year earlier. Supply is steady and demand is absorbing it. A seller competes with recent closings and with the next listing a buyer can choose.
Luxury and new construction
What is happening at the top of the Winter Park market?
Citywide medians say little about a $2 million home. For that, we read closed luxury sales directly.
- New construction clears at $642 to $726 per square foot. That was the band for completed new construction luxury sales in our August 2026 review of Stellar MLS records. Trophy homes printed $875 to $1,150 or more.
- About 4 in 10 active $1M+ listings in core Winter Park were new construction in the same August 2026 pull.
- Buildable lots in core 32789 were asked at roughly $1.4M to $1.5M as of August 2026.
- The Enclave has six residences listed from $1,550,000 to $2,300,000 as of October 10, 2026. See Winter Park new construction.
- A resale example. 151 Oakwood Way, built in 2023, closed on June 18, 2026 for $2,750,000, or $666 per square foot, after a documented path from a $3,180,000 list price. Read the case study.
What to do with it
What does this mean for you?
Launch at the right price
A rising median is not permission to overprice. Two in three sales closed below list. Homes priced right went pending in about three weeks.
Separate the two kinds of listing
Scarce, correctly priced homes move in weeks and leave little room. Listings that have sat or cut their price are where negotiation lives.
Underwrite from the exit
Start with a finished price you can defend from closed sales, then work back through cost, carry and profit to what the lot is worth.
Month over month
What changed since the September report?
| Measure | September edition | October edition |
|---|---|---|
| Redfin median sale price, three months | $799,565, through June | $865,000, through August |
| Redfin homes sold in the month | 151, June | 161, August |
| Zillow typical home value | $469,253 | $464,563 |
| Zillow homes for sale | 374, July | 377, August |
| Zillow new listings | 107, July | 105, August |
| Zillow median sale to list ratio | 0.980, June | 0.981, July |
| Zillow share of sales below list | 65.2%, June | 67.3%, July |
| Zillow median days to pending | 26, June | 22, August |
The September 2026 edition stays online for reference.
Questions
Winter Park market, answered.
Is Winter Park a buyer's or a seller's market in October 2026?
Neither extreme. Redfin rates Winter Park somewhat competitive, with a Compete Score of 44 out of 100. Prices and sales are up from a year ago, but about two in three sales still close below their list price.
What is the median home price in Winter Park, Florida?
$865,000 for the three months ending August 2026, according to Redfin, up 11.6% from a year earlier. Zillow's typical home value, which models all homes rather than only those that sold, was $464,563 as of August 31, 2026.
How long does it take to sell a home in Winter Park?
Zillow's median time to a pending contract was 22 days in August 2026. Redfin's median days on market was 46. Correctly priced homes go under contract in about three weeks.
Are homes in Winter Park selling over asking price?
Few are. Redfin found 11.2% of homes sold above list price in August 2026, and Zillow found 14.9% in July. Most sell slightly below, with a median sale to list ratio near 98%.
What does new construction cost in Winter Park?
Completed new construction luxury sales cleared at $642 to $726 per square foot in an August 2026 review of Stellar MLS records. At The Enclave, six residences were listed from $1,550,000 to $2,300,000 as of October 10, 2026.
How often is this Winter Park market report updated?
Monthly. This edition was reviewed on October 10, 2026. The next edition is November 2026.
Sources and method
Traceable numbers.
- Redfin, Winter Park housing market: sale price, sales count, days on market, sale to list and price drop measures through August 2026.
- Zillow, Winter Park home values: typical value, inventory, new listings and days to pending through August 31, 2026; sale measures through July 31, 2026.
- Burks Holdings review of active and closed Stellar MLS records, August 2026, for the new construction and lot figures. These are labeled separately from the public citywide series.
Each source was read on October 10, 2026. The publication date and the measurement period are not the same thing, so each number carries its own period. Real estate statistics are historical. This is market analysis, not an appraisal or a guarantee of future value. Next edition: November 2026.
Make the number specific to your property.
The useful question is not what Winter Park did. It is what your home, lot or plan competes with. Bring Matthew the address.