Photo: Ebyabe · CC BY-SA 3.0522 homes sold in Winter Park in the last year, at a typical $780K
About one sale in 4 is a condo. Below: what each kind of home sells for, what your budget buys, 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.
A quarter of Winter Park’s sales are condos, at $687K less than a house
372 houses and 111 condos sold in the year to May 2026. Houses sell faster and draw more bidding wars.
typical sale · 372 sold in 12 months
- Per square foot
- $452FL $245
- Days to sell
- 40
- Sold over asking
- 14%
- Listings with a price cut
- 33%
typical sale · 111 sold in 12 months
- Per square foot
- $302FL $262
- Days to sell
- 78
- Sold over asking
- 4%
- Listings with a price cut
- 36%
Multi-family (2–4 units): 2 sold, typical $1M
Townhouses: 37 sold, typical $690K
Too few sales in 12 months for reliable figures.
Fewer homes sell than before 2022, at 2.2 times the 2016 price
522 sales in the last year, against 925 in 2021 and a low of 538 in 2024. The typical sale went from $361K in 2016 to $780K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $800K buys in Winter Park
Check a listing against what Winter Park homes sold for
Against the town’s median price per square foot over the last 12 months. A rough check: condition, lot and location within town move a price more than this can see.
Bidding wars in Winter Park are back to pre-pandemic levels, but a third fewer homes come up 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 May 2026, 522 sales.
If you’re buying in Winter Park
- Shop in January. It brings about 76 new listings a month, close to the busiest month, with fewer bidding wars (9% over asking).
- Some room to negotiate. 33% of listings cut their price, about as many as before the pandemic.
- Offer under asking. Buyers paid 96.5% of the list price on average; 11% paid over.
- You’ll usually have time. Only 33% of homes go under contract within two weeks; the typical one takes 46 days.
Summer brings the homes; spring brings the bidding wars
June has the most new listings (about 89 a month), but April is the most competitive: 17% of April sales close over asking. January and February offer nearly as much choice with fewer homes bid up (9%). January has the least competition (9%).
Averages for each calendar month, 2015 on.
Nearly as heated as 2021, and about like Florida as a whole
| Winter Park now | 2017–19 | 2021 peak | FL now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 11% | 8% | 21% | 10% |
| Gone within two weeksShare of homes under contract within 14 days | 33% | 31% | 46% | 20% |
| Listings with a price cutShare of homes for sale that cut their price | 33% | 31% | 30% | 28% |
| Price paid vs. askingAverage sale price ÷ list price | 96.5% | 96.3% | 98.3% | 96.3% |
| Days to sellMedian days from listing to contract | 46 | 55 | 27 | 76 |
170 homes for sale on a typical day
That’s 1.6 times the 2023 low (105), 37% fewer than in 2017–19 and well under 2012’s 322.
1 in 3 listings has cut its price
33% in the last year, against 31% in 2017–19 and 28% across Florida.
Since 2019, houses are up 75%, condos 72%
A house typically sold for $994K in the last year (372 sales), a condo for $307K (111).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Winter Park ranks 201st of 534 busy Florida 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 market tracker, January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Winter Park home costs about $4,550 a month
Price: Winter Park’s typical sale, last 12 months. Property tax at Winter Park’s 0.7% (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 June
The month with the most choice. December has the fewest, about 43.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $780K home, about $5,760 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.
Maitland, Fairview Shores, Goldenrod, Fern Park, Azalea Park and Casselberry sell for less a square foot
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 | |
|---|---|---|---|---|---|
| Winter Park | 522 | $780K | $408 | 11% | 46 |
| Casselberry | 280 | $336K | $220 | 15% | 39 |
| Maitland | 232 | $551K | $293 | 10% | 49 |
| Fairview Shores | 145 | $354K | $276 | 12% | 64 |
| Goldenrod | 125 | $394K | $239 | 21% | 40 |
| Fern Park | 122 | $410K | $238 | 17% | 53 |
| Azalea Park | 88 | $329K | $249 | 30% | 53 |
Redfin Data Center, June 2025 to May 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, FL?
522 homes sold in the year to May 2026 at a typical $780K, $408 a square foot. Houses sold for about $994K, condos for about $307K.
Is Winter Park a buyer’s or seller’s market?
A seller’s market: 172 homes were for sale in May 2026 and 44 sold, about 3.9 months of supply. Buyers paid 96.5% of asking on average, and 33% of listings cut their price.
When is the best time to buy in Winter Park?
June brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Winter Park?
About 0.7% of a home’s value a year. On a $780K home that’s near $5,760.
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). 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).