Winter Park Single-Family Market Report
In Winter Park, closed-buyer activity increased 25.7% in the latest six months while median sale price increased 18.2% and aggregate median days to contract lengthened from 27 to 35 days.
What is changing
Real Buyers by Month
View monthly data
| Month | Real Buyers |
|---|---|
| Aug 2025 | 37 |
| Sep 2025 | 24 |
| Oct 2025 | 31 |
| Nov 2025 | 25 |
| Dec 2025 | 32 |
| Jan 2026 | 19 |
| Feb 2026 | 21 |
| Mar 2026 | 29 |
| Apr 2026 | 20 |
| May 2026 | 27 |
| Jun 2026 | 50 |
| Jul 2026 | 34 |
| Aug 2026 | 31 |
Median Sale Price by Month
View monthly data
| Month | Median Sale Price |
|---|---|
| Aug 2025 | $1,110,000 |
| Sep 2025 | $1,275,000 |
| Oct 2025 | $1,318,000 |
| Nov 2025 | $1,300,000 |
| Dec 2025 | $978,655 |
| Jan 2026 | $622,500 |
| Feb 2026 | $975,000 |
| Mar 2026 | $1,130,000 |
| Apr 2026 | $1,002,500 |
| May 2026 | $1,500,000 |
| Jun 2026 | $1,162,000 |
| Jul 2026 | $1,895,000 |
| Aug 2026 | $1,100,000 |
Median Days to Contract by Month
View monthly data
| Month | Median Days to Contract |
|---|---|
| Aug 2025 | 43 |
| Sep 2025 | 27 |
| Oct 2025 | 24 |
| Nov 2025 | 37 |
| Dec 2025 | 24 |
| Jan 2026 | 18.5 |
| Feb 2026 | 57.5 |
| Mar 2026 | 60 |
| Apr 2026 | 41 |
| May 2026 | 11.5 |
| Jun 2026 | 35 |
| Jul 2026 | 46 |
| Aug 2026 | 25 |
| 6-month comparison | Previous 6 mos. | Latest 6 mos. | Change |
|---|---|---|---|
| Cash Share | 50.7% | 47.1% | ↓ −3.5 pt |
| Real Buyers | 152 | 191 | ↑ +25.7% |
| Median Sold $/SF | $486.76 | $486.49 | ↓ −0.1% |
| Median Sale Price | $1,100,000 | $1,300,000 | ↑ +18.2% |
| Median Sale Price / Last List Price | 98.0% | 97.0% | ↓ −1.0 pt |
| Median Days to Contract | 27 | 35 | ↑ 8 days |
Where the buyers are
| Price Band | Current Listings | Pending Listings | Real Buyers 13 mos. | Avg. Monthly | Months of Supply |
|---|---|---|---|---|---|
| $0 - $499,999 | 12 | 6 | 63 | 4.8 | 2.5 |
| $500,000 - $749,999 | 13 | 14 | 53 | 4.0 | 3.3 |
| $750,000 - $999,999 | 14 | 3 | 48 | 3.4 | 4.1 |
| $1,000,000 - $1,999,999 | 55 | 8 | 124 | 9.3 | 5.9 |
| $2,000,000 - $3,999,999 | 26 | 8 | 65 | 4.9 | 5.3 |
| $4,000,000 - $5,999,999 | 10 | 3 | 20 | 1.5 | 6.7 |
| $6,000,000 - $7,999,999 | 3 | 0 | 6 | 0.5 | 6.0 |
| $8,000,000 - $9,999,999 | 0 | 0 | 0 | 0.0 | — |
| $10,000,000+ | 0 | 0 | 1 | 0.1 | 0.0 |
Market Activity & Supply by Price Band
View price-band data
| Price Band | Avg. Monthly Real Buyers | Current Listings | Pending Listings |
|---|---|---|---|
| $0 - $499,999 | 4.8 | 12 | 6 |
| $500,000 - $749,999 | 4.0 | 13 | 14 |
| $750,000 - $999,999 | 3.4 | 14 | 3 |
| $1,000,000 - $1,999,999 | 9.3 | 55 | 8 |
| $2,000,000 - $3,999,999 | 4.9 | 26 | 8 |
| $4,000,000 - $5,999,999 | 1.5 | 10 | 3 |
| $6,000,000 - $7,999,999 | 0.5 | 3 | 0 |
| $8,000,000 - $9,999,999 | 0.0 | 0 | 0 |
| $10,000,000+ | 0.1 | 0 | 0 |
Months of Supply by Price Band
View price-band data
| Price Band | Months of Supply |
|---|---|
| $0 - $499,999 | 2.5 |
| $500,000 - $749,999 | 3.3 |
| $750,000 - $999,999 | 4.1 |
| $1,000,000 - $1,999,999 | 5.9 |
| $2,000,000 - $3,999,999 | 5.3 |
| $4,000,000 - $5,999,999 | 6.7 |
| $6,000,000 - $7,999,999 | 6.0 |
| $8,000,000 - $9,999,999 | — |
| $10,000,000+ | 0.0 |
How transactions are clearing
| Price Band | Real Buyers | Median Sale Price | Median Sold $/SF | Median DTC | Sale / Last List | Cash | Cash Share |
|---|---|---|---|---|---|---|---|
| $0 - $499,999 | 63 | $406,000 | $298.66 | 32 | 98.0% | 24 | 38.1% |
| $500,000 - $749,999 | 53 | $615,000 | $390.57 | 39 | 97.0% | 28 | 52.8% |
| $750,000 - $999,999 | 48 | $843,250 | $443.74 | 25 | 98.5% | 23 | 47.9% |
| $1,000,000 - $1,999,999 | 124 | $1,450,000 | $499.08 | 37 | 98.0% | 57 | 46.0% |
| $2,000,000 - $3,999,999 | 65 | $2,650,000 | $655.37 | 51 | 96.0% | 32 | 49.2% |
| $4,000,000 - $5,999,999 | 20 | $4,635,000 | $872.22 | 11.5 | 97.0% | 16 | 80.0% |
| $6,000,000 - $7,999,999 | 6 | $6,400,000 | $1,130.40 | 6.5 | 98.5% | 5 | 83.3% |
| $8,000,000 - $9,999,999 | 0 | — | — | — | — | 0 | — |
| $10,000,000+ | 1 | $13,000,000 | $1,066.45 | 4 | 101.0% | 1 | 100.0% |
Market Time by Price Band
View price-band data
| Price Band | Median DTC (Real Buyers) | Median Active CDOM |
|---|---|---|
| $0 - $499,999 | 32 | 72 |
| $500,000 - $749,999 | 39 | 119 |
| $750,000 - $999,999 | 25 | 60 |
| $1,000,000 - $1,999,999 | 37 | 71 |
| $2,000,000 - $3,999,999 | 51 | 67 |
| $4,000,000 - $5,999,999 | 11.5 | 49 |
| $6,000,000 - $7,999,999 | 6.5 | 117 |
| $8,000,000 - $9,999,999 | — | — |
| $10,000,000+ | 4 | — |
Median Sale Price / Last List Price by Price Band
View price-band data
| Price Band | Median Sale / Last List |
|---|---|
| $0 - $499,999 | 98.0% |
| $500,000 - $749,999 | 97.0% |
| $750,000 - $999,999 | 98.5% |
| $1,000,000 - $1,999,999 | 98.0% |
| $2,000,000 - $3,999,999 | 96.0% |
| $4,000,000 - $5,999,999 | 97.0% |
| $6,000,000 - $7,999,999 | 98.5% |
| $8,000,000 - $9,999,999 | — |
| $10,000,000+ | 101.0% |
MLS Listing Outcomes
MLS Listing Outcomes by Price Band
View price-band data
| Price Band | Closed Share | Expired Share | Cancelled Share |
|---|---|---|---|
| $0 - $499,999 | 82% | 4% | 14% |
| $500,000 - $749,999 | 76% | 3% | 21% |
| $750,000 - $999,999 | 71% | 3% | 26% |
| $1,000,000 - $1,999,999 | 69% | 9% | 22% |
| $2,000,000 - $3,999,999 | 58% | 12% | 31% |
| $4,000,000 - $5,999,999 | 56% | 11% | 33% |
| $6,000,000 - $7,999,999 | 75% | 0% | 25% |
| $8,000,000 - $9,999,999 | 0% | 0% | 100% |
| $10,000,000+ | 33% | 0% | 67% |
What the outcomes show
Observed MLS listing outcomes are not probabilities and may include more than one record for the same property. Among bands with normal sample depth, the highest closed shares were recorded from $0 - $499,999 (82%), from $500,000 - $749,999 (76%) and from $750,000 - $999,999 (71%). At $10M+, of 3 observed outcome records, 1 closed and 2 were canceled. With only 3 records, that result should be treated as a factual observation, not a failure rate or a prediction of future listing outcomes.
What the Numbers Mean
Cash share decreased from 50.7% to 47.1%. Closed-buyer activity increased from 152 in the previous six months to 191 in the latest six months, an increase of 25.7%. Median sold price per square foot decreased 0.1% to $486.49. Median sale price increased 18.2% to $1,300,000. Aggregate median days to contract lengthened from 27 to 35 days. Current inventory stands at 133 active listings, equal to 4.7 months of supply using the latest 12-month closing pace. Months of supply is lower in $0 - $499,999 than in $4,000,000 - $5,999,999. $10,000,000+ has 1 observed closed transaction. That sample is too small to support a stable conclusion about buyer or seller leverage.
For Sellers
Market conditions change materially by price band. Months of supply is lower in $0 - $499,999 than in $4,000,000 - $5,999,999. $10,000,000+ has 1 observed closed transaction. That sample is too small to support a stable conclusion about buyer or seller leverage. As values rise and samples thin, a property's immediate competitive set and the most relevant comparable sales should carry more weight than broader market medians.
For Buyers
Negotiating position depends on band-level supply and recent closed pace. Months of supply is lower in $0 - $499,999 than in $4,000,000 - $5,999,999. $10,000,000+ has 1 observed closed transaction. That sample is too small to support a stable conclusion about buyer or seller leverage. Compare each property with its active competitive set and the most relevant recent sales rather than relying on broader market medians alone.
Data notes
Real Buyers are closed MLS listings with a valid Close Date inside the inclusive report period.
Current Listings count strict ACT status only; pending statuses are reported separately.
The report uses 13 months of closed-sale data for full-period statistics and monthly trend context. Months of Supply uses the monthly pace of closed buyers in the latest 12 complete calendar months within that 13-month window.
Months of Supply equals ACT listings divided by that monthly pace (ACT / monthly pace).
Price bands use lower-inclusive and upper-exclusive boundaries; the final $10,000,000+ band is open-ended.
Contiguous empty price bands below the lowest occupied band and above the highest occupied band are omitted from presentation; internal zero bands remain visible.
Medians ignore missing or invalid values and average the two middle observations for even samples.
MLS Listing Outcomes summarize observed SLD, EXP, and CAN records; they are not probabilities and may include more than one record for the same property.
A Market Report Is Context.
Your Property Requires Its Own Analysis.
Winter Park is a segmented market. Location within the community, architecture, condition, improvements, lot characteristics, amenities, and competitive position can materially affect how an individual property should be priced and positioned.
If you would like my opinion on where your property fits within the current market, text or call me directly.