Winter Park Home Values (2026): What Houses Are Actually Selling For
Winter Park, Orange County, Florida · Momentum Research · updated 2026-09-25
Homes in Winter Park sold for a median of $449,000 over the last 12 months (850 recorded sales), $270 per square foot, and prices are up 1.6% year over year. The typical sale took 33 days to go under contract and closed at 95.6% of the original asking price. Long run: 4.7% a year since 2012 (median $238K then). No algorithm can price your specific house from that; a records-based valuation can. The data first, then how to get one.
Winter Park home values year by year
Median recorded sale price, price per square foot, days to contract and sale-to-ask for every year we hold Winter Park sales. The compound growth rate works out to 4.7% a year since 2012 (median $238K then).
| Year | Median sale | $/sq ft | Days to contract | Sale-to-ask | Sales |
|---|---|---|---|---|---|
| 2012 | $237,555 | $111 | 46 | 90.4% | 138 |
| 2013 | $225,327 | $122 | 25 | 95.1% | 177 |
| 2014 | $282,055 | $135 | 41 | 94.3% | 464 |
| 2015 | $259,379 | $143 | 42 | 95.1% | 868 |
| 2016 | $301,699 | $155 | 37 | 95.6% | 1,171 |
| 2017 | $332,902 | $174 | 38 | 95.3% | 1,008 |
| 2018 | $451,748 | $198 | 57 | 95.0% | 212 |
| 2019 | $457,423 | $225 | 98 | 92.0% | 63 |
| 2021 | $490,389 | $235 | 7 | 99.5% | 193 |
| 2022 | $462,543 | $258 | 9 | 99.2% | 1,182 |
| 2023 | $497,761 | $279 | 20 | 96.1% | 368 |
| 2024 | $607,862 | $308 | 21 | 95.9% | 928 |
| 2025 | $619,722 | $317 | 33 | 94.3% | 959 |
| 2026 | $647,825 | $327 | 34 | 95.6% | 850 |
Where the Winter Park market is tight, by price band
Months of supply is active inventory divided by the monthly sales pace; under about four months favors sellers, over six favors buyers. Find your band before you price.
| Price band | Active now | Sold (12 mo) | Months of supply | Days to contract |
|---|---|---|---|---|
| Under $300K | 38 | 131 | 3.5 | 68 |
| $300K–$500K | 15 | 86 | 2.1 | 23 |
| $500K–$750K | 21 | 97 | 2.6 | 25 |
| $750K+ | 54 | 180 | 3.6 | 46 |
Winter Park home values by ZIP code
Active listings and list medians from our feeds today; the typical value and one-year change are Zillow’s ZHVI for the ZIP, which tracks the whole housing stock rather than only what sold.
| ZIP | Active listings | Median list | Typical value (ZHVI) | 1-yr change | Listings with a price cut |
|---|---|---|---|---|---|
| 32789 | 219 | $1,250,000 | $811,947 | +5.6% | 30% |
| 32792 | 145 | $429,900 | $394,154 | -0.2% | 28% |
Home values by community in Winter Park
The communities with the most recorded sales in the last 12 months. Each links to its own home-value page with the full price history.
| Community | Median sale | Year over year | Days to contract | Sales (12 mo) | Active |
|---|---|---|---|---|---|
| Kenilworth Shores Sec 1 | $635,000 | -2.3% | 5 | 31 | 0 |
| Eastbrook Sub Unit 8 | $373,000 | -2.4% | 28 | 28 | 0 |
| EASTBROOK SUB UNIT 05 | $370,000 | -2.6% | 30 | 23 | 0 |
| KENILWORTH SHORES SEC 06 | $627,000 | -16.4% | 5 | 23 | 0 |
| winter park pines | $600,000 | +13.2% | 19 | 23 | 8 |
| Four Seasons Condo | $180,000 | -1.4% | 35 | 21 | 0 |
| country lane | $386,000 | n/a | 10 | 14 | 0 |
| Comstock Park | $1,700,000 | +100.0% | 25 | 13 | 2 |
| Garden Lake Estates Unit 3 | $449,000 | +5.0% | 15 | 13 | 0 |
| Winter Park Woods Condo | $78,000 | -22.0% | 12 | 13 | 1 |
| Windward Square Sec 3 | $273,625 | +0.4% | 10 | 12 | 0 |
| Charmont | $1,000,500 | -42.0% | 35 | 11 | 5 |
Communities moving fastest in Winter Park
Rising: winter park pines (+13%). Year-over-year change in median recorded sale; small communities swing on a handful of sales, so read these as leads, not verdicts.
What moves the sale price in Winter Park beyond the medians
Cash paid for about 31% of recent Winter Park closings. New construction was 3% of sales, which sets the ceiling on what resale buyers will pay for a comparable resale. Sellers have been closing at 95.6% of original asking, so the list price is a negotiation opener, not the number. Zillow’s ZIP metrics put the city’s price-to-income ratio near 5.2 and five-year appreciation near +4.3%. Property mix: Single Family Residence 81%, Townhouse 10%, Condominium 7%. Condition, lot, roof age, insurance quote and the specific street’s last three closings move an individual house well outside these ranges.
What is my house worth in Winter Park?
Not a number this page can give you, and not one an automated model can either: every value above is a median of many Winter Park sales, and the spread inside it is wide. A records-based valuation pulls the recorded closings on your street and in your community, adjusts for size, condition, lot and what your home has that the comps do not, and comes back as a written range with a net sheet showing what you would clear at each price after commissions, Florida doc stamps, title and payoff. Momentum Realty does that for Winter Park owners at no cost through the form below; the Messtimate gives a square-footage range in the meantime, and the seller net proceeds calculator runs the arithmetic on any price you are considering.
Selling in Winter Park: next steps
- Best time of year to sell in Orange County
- Seller net proceeds calculator
- Orange County property tax rate and calculator (what a buyer will pay after your sale)
- Homes for sale in Winter Park right now (your competition)
- Winter Park housing market: live data and trends
- How to choose a listing agent in Winter Park
- How Momentum sells homes
Frequently asked questions
What is the median home price in Winter Park, FL?
How long does it take to sell a house in Winter Park?
Are home prices in Winter Park going up or down?
What is my house worth in Winter Park?
Which Winter Park communities hold value best?
Figures are recorded closed sales and active listings from the MLS feeds behind our Winter Park pages, aggregated by Momentum Research as of 2026-09-25; ZIP typical values from Zillow (ZHVI). Community-level aggregates only; nothing on this page is a valuation of any specific property, an appraisal, or an offer. Deemed reliable but not guaranteed. EAB RE Investments LLC dba Momentum Realty, a licensed Florida real estate brokerage. Equal Housing Opportunity.