Winter Park
Housing Market
Median sale price $447,000, down 3.3% year over year, with homes going under contract in about 32 days, 92 homes on the market.
Momentum
Your exact situation run against today's numbers: true comps, negotiation targets, and the off-market homes portals never show.
Selling instead? See what your home is worth today →
Housing Market Analyst
Inventory sits at 4.2 months of supply — balanced by the 3-to-6-month balanced benchmark, and 36% of listed homes are already under contract. Prices are down 3.3% versus the prior year, but sellers are still collecting 95.4% 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 — sellers hold the leverage while 36% of inventory sits under contract.
- Mortgage sensitivity — at 5.3× 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 (130 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 $447,000, down 3.3% from a year ago. Buyers are paying a median of $270 per square foot. The typical home goes under contract in about 32 days. Sellers are capturing 95.4% of their original asking price on average.
There are 92 active listings on the market, with 27 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. 357 homes closed here over the trailing 12 months.
Zillow's home value index for Orange County stands at $404,958. About 26% 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 62 of 100 — balanced market territory. This page recalculates every day as new MLS data lands, so the numbers above reflect the market as of August 6, 2026.
Winter Park since 2012 — and where it’s heading
A median home here sold for $247,917 in 2012 and $596,865 over the last recorded year — 141% appreciation across 14 years of recorded sales. Cash buyers took 41% of recent sales, down from a 42% peak.
Median sale price · 2012–2026 (8,745 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)
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.
Sellers: price to the last 60 days of comps, not the peak — well-prepared listings are still commanding strong terms. Buyers: get underwritten now so you can move when the right house hits.
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 | $447K | 92 | 62 | |
| Orlando | $408K | 1,352 | 58 | Open → |
| Winter Garden | $595K | 299 | 62 | Open → |
| Apopka | $395K | 236 | 70 | Open → |
| Windermere | $640K | 123 | 58 | Open → |
| Ocoee | $475K | 52 | 73 | Open → |
Neighborhoods on the move
| COMSTOCK PARKWinter Park | $1.30M | ▲ 12% |
| WINTER PARK PINESWinter Park | $587K | ▲ 11% |
| GARDEN GROVEWinter Park | $261K | ▲ 9% |
| CASA ALOMAWinter Park | $448K | ▲ 5% |
| GARDEN LAKE ESTATES UNIT 1Winter Park | $447K | ▲ 5% |
| CHARMONTWinter Park | $1.00M | ▼ 38% |
| VILLAS OF CASSELBERRY PH 2Winter Park | $282K | ▼ 19% |
| Villas Of Casselberry Phase 3Winter Park | $282K | ▼ 19% |
| ORWIN MANOR WESTMINSTER SECWinter Park | $610K | ▼ 17% |
| KENILWORTH SHORES SEC 06Winter Park | $627K | ▼ 16% |
| WINTER PARK PINESWinter Park | $587K | 9 |
| COLONIESWinter Park | $90K | 4 |
| LAWNDALEWinter Park | $735K | 4 |
| WINTER PARK WOODS CONDOWinter Park | $78K | 4 |
| CHARMONTWinter Park | $1.00M | 3 |
| KENILWORTH SHORES SEC 06Winter Park | $627K | 5 days |
| Kenilworth Shores Sec 1Winter Park | $627K | 5 days |
| TANGLEWOOD SEC 3 REPWinter Park | $382K | 6 days |
| COUNTRY LANEWinter Park | $388K | 10 days |
| WINTER PARK WOODS CONDOWinter Park | $78K | 10 days |
Winter Park ZIP codes
Most active communities
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 62/100 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?
Yes, modestly — the median sale price in Winter Park is $447,000, down 3.3% versus the prior year, while sellers still capture 95.4% of asking price. Softening prices plus normal-length marketing times mean affordability is improving at the margin, though financing costs matter more than list prices for most monthly payments.
Where are prices falling fastest in Winter Park?
Among tracked communities with enough sales to measure, the sharpest 1-year median declines are CHARMONT (-38%); VILLAS OF CASSELBERRY PH 2 (-19%); Villas Of Casselberry Phase 3 (-19%). 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 KENILWORTH SHORES SEC 06 (5 days); Kenilworth Shores Sec 1 (5 days); TANGLEWOOD SEC 3 REP (6 days) — homes there go under contract well ahead of the market-wide pace of 32 days.
How does Winter Park compare to the rest of Orange County?
Winter Park's median of $447,000 runs 3% below the county-wide median of $458,500, and homes here take 32 days to go under contract versus 42 county-wide.
Winter Park housing market FAQ
What is the median home price in Winter Park?
The median sale price in Winter Park is currently $447,000, down 3.3% from a year ago, based on MLS sales data updated August 6, 2026.
Is Winter Park a buyer's or seller's market right now?
The data currently favors sellers. Winter Park scores 62 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 32 days, per current MLS data.
How many homes are for sale in Winter Park?
There are approximately 92 active listings in Winter Park as of August 6, 2026.
Are home prices in Winter Park rising or falling?
Median sale prices are down 3.3% 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: August 6, 2026 at 7:18 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.