Winter Park
Housing Market
Median sale price $459,450, up 1.8% year over year, with homes going under contract in about 34 days, 124 homes on the market.
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Housing Market Analyst
Inventory sits at 4.2 months of supply — balanced by the 3-to-6-month balanced benchmark, and 20% of listed homes are already under contract. Prices are up 1.8% versus the prior year and sellers are still collecting 95.5% of asking. Taken together, the data points to a broadly balanced market where preparation decides who wins.
Who has leverage right now
Leverage scores are derived from the Momentum Score (supply, demand, speed, pricing power, and trend). Right now the data favors sellers.
- Prices — balanced supply argues for a sideways market; condition and pricing decide individual outcomes.
- Inventory — building over the tracked window; watch whether that holds through the season.
- Negotiating power — buyers gain ground as 20% of inventory sits under contract.
- Mortgage sensitivity — at 5.2× income, this market is highly sensitive to rate moves; rate relief tends to show up in demand here quickly.
Derived from current Winter Park data, not a prediction or guarantee. Markets move; talk to an agent before acting on any single reading.
One inventory number hides four different markets
Months of supply = active listings ÷ monthly sales pace, bucketing communities by their recent median. 3–6 months is the balanced band.
Where Winter Park is hot — and where it isn't
Each dot is a community (127 shown, sized by sales volume rank). Click any dot to open its full neighborhood guide.
The read on Winter Park
The median sale price across Winter Park currently stands at $459,450, up 1.8% from a year ago. Buyers are paying a median of $272 per square foot. The typical home goes under contract in about 34 days. Sellers are capturing 95.5% of their original asking price on average.
There are 124 active listings on the market, with 28 more already under contract. At the current sales pace that works out to 4.2 months of supply — roughly balanced conditions by the standard six-month benchmark. 494 homes closed here over the trailing 12 months.
Zillow's home value index for Orange County stands at $403,786. About 27% of listings county-wide have taken a price cut — a useful gauge of seller flexibility.
Weighing supply, demand, speed, pricing power, and trend together, the Momentum Score for Winter Park is 58 of 100 — balanced market territory. This page recalculates every day as new MLS data lands, so the numbers above reflect the market as of September 15, 2026.
Winter Park since 2012 — and where it’s heading
A median home here sold for $237,928 in 2012 and $644,104 over the last recorded year — 171% appreciation across 14 years of recorded sales. Cash buyers took 31% of recent sales, down from a 46% peak.
Median sale price · 2012–2026 (8,585 recorded sales)
Days on market by year
Cash buyers · share of sales
Home value trend · Orange County (Zillow ZHVI)
For-sale inventory · county (Zillow)
Daily active vs pending · Orange County (MLS)
Median price · daily recalculation
What’s driving Winter Park
Top inbound states: NY, CA, NJ, TX. Movers arriving report ~$66,457 average income. Source: IRS SOI county-to-county migration, 2022-2023
4,204 Citizens policies in force in Orange County — the state-backed insurer of last resort. Budget insurance into any Orange purchase before you fall in love with a house. Source: Citizens Property Insurance, Detail by County, April 2026
4,221 single-family · 8,919 multi-family · 9.1 per 1,000 residents. Future supply pressure starts here. Source: U.S. Census Bureau, Building Permits Survey, 2025
The calls we’re making from today’s data
The sharpest 1-yr median swing among tracked communities. Thin samples can exaggerate swings — verify with a comp analysis before treating it as trend.
The most crowded shelf in the market. Sellers here are competing hardest — which means overpaying in this band is the most avoidable mistake in Winter Park right now.
The tightest band — sellers in this range hold the most leverage, and buyers should walk in with financing done and terms clean.
Both sides have a case: buyers should negotiate on days-on-market, sellers should lean on the under-contract rate. Preparation, not the market, decides who wins a balanced tape.
Generated from today’s data by Momentum’s analysis engine and reviewed on a rolling basis by our broker team.
How it stacks up across Orange County
| Market | Median | Active | Score | |
|---|---|---|---|---|
| Winter Park ← this page | $459K | 124 | 58 | |
| Orlando | $412K | 1,608 | 58 | Open → |
| Winter Garden | $595K | 348 | 62 | Open → |
| Apopka | $406K | 229 | 70 | Open → |
| Windermere | $640K | 100 | 60 | Open → |
| Ocoee | $475K | 53 | 77 | Open → |
Neighborhoods on the move
| winter park pinesWinter Park | $600K | ▲ 14% |
| Garden Lake Estates Unit 3Winter Park | $459K | ▲ 8% |
| Greenview At Winter PinesWinter Park | $700K | ▲ 6% |
| GARDEN LAKE ESTATES UNIT 1Winter Park | $447K | ▲ 5% |
| Winter Park Gardens CondoWinter Park | $265K | ▲ 4% |
| Karolina On KillarneyWinter Park | $483K | ▼ 49% |
| VILLAS OF CASSELBERRY PH 2Winter Park | $282K | ▼ 19% |
| KENILWORTH SHORES SEC 06Winter Park | $627K | ▼ 16% |
| Orwin Manor Westminster SecWinter Park | $618K | ▼ 16% |
| Parkview VillageWinter Park | $155K | ▼ 16% |
| winter park pinesWinter Park | $600K | 9 |
| CharmontWinter Park | $1.48M | 5 |
| Golfside Villas CondoWinter Park | $119K | 5 |
| LawndaleWinter Park | $968K | 5 |
| ColoniesWinter Park | $90K | 4 |
| Winter Park Estates Sec 2Winter Park | $399K | 4 days |
| KENILWORTH SHORES SEC 06Winter Park | $627K | 5 days |
| Kenilworth Shores Sec 1Winter Park | $635K | 5 days |
| Tanglewood Sec 3 RepWinter Park | $382K | 6 days |
| country laneWinter Park | $386K | 10 days |
Winter Park ZIP codes
Most active communities
More on Winter Park
Put this data to work
The questions people actually ask
Should I buy a house in Winter Park right now?
The data says conditions currently favor neither side decisively in Winter Park — the Momentum Score reads 58/100 with 4.2 months of supply. For buyers that means preparation over hesitation: well-priced homes still move fast, but there is more room to negotiate than a year ago. The right timing always depends on your rate, your equity, and how long you plan to stay — not just the market.
Is Winter Park becoming more affordable?
No — the median sale price in Winter Park is $459,450, up 1.8% versus the prior year, while sellers still capture 95.5% of asking price. Rising prices mean waiting has a cost; affordability hinges mostly on your rate.
Where are prices falling fastest in Winter Park?
Among tracked communities with enough sales to measure, the sharpest 1-year median declines are Karolina On Killarney (-49%); VILLAS OF CASSELBERRY PH 2 (-19%); KENILWORTH SHORES SEC 06 (-16%). Note that community-level medians move on small sale counts — a few high- or low-end closings can swing them — so treat these as leads for a comp analysis, not verdicts.
Which Winter Park neighborhoods are most competitive?
Measured by speed of sale, the fastest-moving tracked communities right now are Winter Park Estates Sec 2 (4 days); KENILWORTH SHORES SEC 06 (5 days); Kenilworth Shores Sec 1 (5 days) — homes there go under contract well ahead of the market-wide pace of 34 days.
How does Winter Park compare to the rest of Orange County?
Winter Park's median of $459,450 runs 1% below the county-wide median of $462,500, and homes here take 34 days to go under contract versus 40 county-wide.
Winter Park housing market FAQ
How is the housing market in Winter Park right now?
As of September 15, 2026, the Winter Park housing market favors sellers: the median sale price is $459,450 (up 1.8% year over year), 124 homes are for sale against 494 sales in the last 12 months, which is 4.2 months of supply, and the typical home goes under contract in about 34 days.
How much is a house in Winter Park?
The median home sold for $459,450 in Winter Park over the last 12 months, about $272 per square foot; asking prices on the 124 current listings run from well below to well above that, and the community pages linked below show what each neighborhood actually sells for.
Is it a good time to sell a house in Winter Park?
By the numbers, sellers in Winter Park are getting 95.5% of asking price and going under contract in about 34 days with 4.2 months of supply. Under four months of supply generally favors sellers; over six favors buyers. Whether it is a good time for you depends on what you paid and where you are going next, which is a conversation with an agent, not a chart.
What is the Winter Park housing market forecast?
Momentum Realty publishes the recorded trend, not a prediction: Winter Park median sale prices are up 1.8% year over year, inventory stands at 4.2 months of supply, and 20% of listings are under contract. The charts on this page update with every MLS refresh, so the direction shows up here before any forecast catches it.
What is the median home price in Winter Park?
The median sale price in Winter Park is currently $459,450, up 1.8% from a year ago, based on MLS sales data updated September 15, 2026.
Is Winter Park a buyer's or seller's market right now?
The data currently favors sellers. Winter Park scores 58 of 100 on the Momentum Score, with 4.2 months of housing supply. Conditions change; this page updates daily.
How long do homes take to sell in Winter Park?
The typical home in Winter Park goes under contract in about 34 days, per current MLS data.
How many homes are for sale in Winter Park?
There are approximately 124 active listings in Winter Park as of September 15, 2026.
Are home prices in Winter Park rising or falling?
Median sale prices are up 1.8% year over year based on a rolling comparison of MLS sales.
Momentum agents use this intelligence every day to price listings and write winning offers across Winter Park. Talk through what the numbers mean for your move.
Every number on this page is computed directly from licensed Florida MLS feeds, recorded public sales, Zillow Research, and U.S. Census data — nothing is manually adjusted or estimated by hand. Medians use recorded closed sales; supply figures use live listing counts refreshed twice daily; the Momentum Score methodology is summarized .
Analyst oversight: Jon Brooks — Co-Founder, Momentum Realty · CEO, Momentum Research · Housing Market Analyst · methodology reviewed quarterly · Last data refresh: September 15, 2026 at 7:33 PM ET
Statistics on this page are computed automatically from licensed MLS feeds and public data sources (Zillow Research, U.S. Census Bureau) and summarized without manual review. Figures are estimates based on recent recorded activity, are deemed reliable but not guaranteed, and should be verified with a licensed agent before making decisions. This page does not constitute an appraisal or an automated valuation of any specific property. Momentum Realty is licensed in Florida and Georgia. Equal Housing Opportunity.