Photo: Darkshark0159 at English Wikipedia · Public domain245 homes sold in Winter Park in the last year, at a typical $973K
Almost every sale is a house. Below: what each kind of home sells for, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Winter Park homes are listed.
Every place Winter Park homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Winter Park.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
Houses are 0% of Winter Park’s sales, at a typical — (year to May 2026)
245 homes sold in the year to September 2026.
About as many homes sell as usual, at 4 times the 2016 price
245 sales in the last year, against 330 in 2020 and a low of 43 in 2012. The typical sale went from $241K in 2016 to $973K.
Source: Redfin Data Center, MLS sales; from June 2026 each month is a 3-month rolling window, its counts divided by 3. Typical price and $/sq ft are the monthly medians, weighted by sales. Redfin stopped publishing towns’ figures by property type after May 2026, so houses and condos are shown for the year to then.
Bidding wars in Winter Park are rarer than before the pandemic, and more homes are for sale
We read every month of Winter Park’s home sales since 2012 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to September 2026, 245 sales.
If you’re buying in Winter Park
- Shop in September. It brings about 28 new listings a month, close to the busiest month, with fewer bidding wars (18% over asking).
- Bid near asking. Buyers paid 98% of the list price on average; 14% paid over.
- You’ll usually have time. Only 19% of homes go under contract within two weeks; the typical one takes 90 days.
Summer brings the homes; winter brings the bidding wars
July has the most new listings (about 33 a month), but December is the most competitive: 27% of December sales close over asking. August and September offer nearly as much choice with fewer homes bid up (20%). February has the least competition (17%) but only about 17 new listings.
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and about like Colorado as a whole
| Winter Park now | 2017–19 | 2021 peak | CO now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 14% | 23% | 41% | 18% |
| Gone within two weeksShare of homes under contract within 14 days | 19% | 3% | 4% | 31% |
| Price paid vs. askingAverage sale price ÷ list price | 98% | 99% | 101.9% | 98.3% |
| Days to sellMedian days from listing to contract | 90 | 64 | 47 | 52 |
109 homes for sale on a typical day
That’s twice the 2023 low (51), 24% more than in 2017–19 and well under 2014’s 158.
Winter Park ranks 73rd of 124 busy Colorado markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Winter Park is in the middle of the pack.
Source: Redfin Data Center, city figures, January 2012 to September 2026 (MLS sales, not seasonally adjusted; from June 2026 each month is a 3-month rolling window, its counts divided by 3). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Winter Park home costs about $5,362 a month
Price: Winter Park’s typical sale, last 12 months. Property tax at Winter Park’s 0.4% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Winter Park is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in July
The month with the most choice. January has the fewest, about 16.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $973K home, about $3,420 a year.
Taxes vs. neighborsSchools
The schools grade for Winter Park, from test results, graduation and how much students grow.
Schools in Winter ParkTypical commute
The average one-way trip to work for people who live in Winter Park.
Work & commuteCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
Fraser, St. Mary's, Georgetown, Granby and Nederland sell for less a square foot; Keystone for far more
The busier markets within 25 miles of Winter Park, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Keystone | 281 | $1.2M | $1,007 | 8% | 198 |
| Winter Park | 245 | $973K | $753 | 14% | 90 |
| Granby | 142 | $684K | $448 | 5% | 105 |
| Fraser | 90 | $1M | $606 | 14% | 86 |
| Georgetown | 31 | $523K | $388 | 9% | 71 |
| Nederland | 23 | $802K | $384 | 12% | 62 |
| St. Mary's | 21 | $731K | $371 | 2% | 81 |
Redfin Data Center, October 2025 to September 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Winter Park, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Winter Park. People who follow the town see it, and so do people comparing Winter Park with their own town. No commission, no listing fee.
Questions about buying a home in Winter Park
What do homes sell for in Winter Park, CO?
245 homes sold in the year to September 2026 at a typical $973K, $753 a square foot.
Is Winter Park a buyer’s or seller’s market?
A buyer’s market: 131 homes were for sale in September 2026 and 20 sold, about 6.6 months of supply. Buyers paid 98% of asking on average.
When is the best time to buy in Winter Park?
July brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Winter Park?
About 0.4% of a home’s value a year. On a $973K home that’s near $3,420.
Where can I see homes for sale in Winter Park?
Zillow, Redfin, Realtor.com and Homes.com all carry Winter Park’s MLS listings; the search links above open each one filtered to Winter Park.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted; from June 2026 each month is a 3-month rolling window, its counts divided by 3). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).