+11.5%
Closed-sale count · year over year
Redfin reported 151 June sales versus 135 a year earlier. Transactions are happening. Liquidity has not disappeared.
The executive read
Liquidity is healthy. Pricing forgiveness is not.
Redfin recorded more closings and a higher recent median price, while Zillow found most homes still sold below their final asking price. That combination signals an active market with selective buyers—not a market where every listing has equal leverage.
0.980
Median sale-to-list ratio
Zillow's June measure implies a typical two-percent negotiation from the final asking price. The initial list price can still be farther from the close.
25–26 days
Independent velocity consensus
Zillow's days-to-pending and Redfin's median days-on-market measures nearly agree. Correctly positioned homes are finding decisions in roughly four weeks.
107
New listings · July 2026
Against 374 active listings, new supply continues to enter. Sellers compete not only with recent closings, but with the next property a buyer can choose.
The market is rewarding specificity: the right product, on the right site, at a price the next buyer can defend.
Why the numbers look contradictory
$469K and $800K can both be true.
Zillow's $469,253 figure is a modeled typical home value across Winter Park. Redfin's $799,565 figure is the median price of homes that actually sold during a recent three-month window. One estimates the level of the housing stock; the other describes the mix of recent transactions.
| Measure | Latest reading | What it answers | What it cannot answer |
|---|---|---|---|
| Zillow Home Value Index | $469,253 · +0.6% YoY | How the modeled typical home value is changing. | What a specific luxury home or buildable lot will sell for. |
| Redfin median sale price | $799,565 · +10.3% YoY | What the middle transaction in the recent sales mix looked like. | Whether every property gained 10.3% in value. |
| Zillow sale-to-list ratio | 0.980 | How closings compared with final asking prices. | How far the original list price was reduced before contract. |
| Burks luxury/new-build audit | $642–$726/sf clearing band | Where completed new-construction luxury sales clustered in the August 2026 Stellar MLS review. | A valuation of a site without its plans, location, costs and buyer profile. |
Never combine these into one “Winter Park price.” Each measure has a different population, period and methodology. That distinction is the analysis.
The luxury and development layer
Citywide data is context. The parcel is the deal.
Luxury value in Winter Park is discontinuous. Lake position, street, tree constraints, lot width, architectural quality and finished program can move value faster than a citywide index.
For sellers
Do not use a rising median as permission to overprice. Sixty-five percent of Zillow-tracked June sales finished below asking. Launch position and competitive replacement matter.
For buyers
A fast median market time does not eliminate negotiation. Separate scarce, correctly priced product from listings whose ask is unsupported by site, condition or replacement cost.
For builders
Underwrite backward from a defensible finished exit. The lot residual must absorb hard cost, soft cost, carry, selling expense, contingency and profit—not just match a nearby land ask.
For landowners
Your highest buyer may value the property as a future home, not as today's structure. Confirm zoning, lot-of-record status, trees, setbacks and buildable envelope before pricing the dirt.
Sources and method
Traceable numbers. Separated correctly.
This report uses the latest available observation from each source as of September 3, 2026. Publication date and measurement period are not assumed to be the same.
- Zillow Winter Park Housing Market — values and inventory through July 31, 2026; sale-to-list measures through June 30, 2026.
- Redfin Winter Park Housing Market — three-month sales measures through June 2026.
- City of Winter Park Building & Permitting Services — current permit resources and regulatory notices.
- Burks Holdings August 2026 audit — active and closed Stellar MLS records used for the luxury new-construction and teardown analysis. Figures are labeled separately from public citywide series.
Real estate statistics are historical and property-specific advice requires current comparable sales, physical due diligence and professional review. This is market analysis, not an appraisal, engineering opinion or guarantee of future value.
Make the number property-specific
Bring Matthew the address, lot or plan.
The useful question is not “What did Winter Park do?” It is “What does this property compete with, and what decision does that support?”
Call Matthew · (407) 257-5347