Winchester, MA Housing Market Report — August 2026
Bean Group · Published
Market update
Market at a glance
August 2026 · Single-family residences
$1,750,000
Median sale price
Year to date
−7.2%
121
Homes sold
Year to date
+6.1%
119
Under contract
Year to date
−8.5%
34
Homes for sale
August 2026
+9.7%
Changes compare with the same period one year earlier.
In August 2026, Winchester recorded 12 single-family closings, compared with 17 in August 2025. The median sale price was $1,950,000, compared with $1,775,000 a year earlier.
Through August 2026, Winchester recorded 121 closings and a $1,750,000 median sale price, compared with 114 closings and $1,885,950 through August 2025.
At the end of August, Winchester had 34 single-family homes for sale, compared with 31 a year earlier, and 2.3 months of inventory.
August 2026 compared with August 2025
| Metric | August 2026 | August 2025 | Change |
|---|---|---|---|
| Pending sales | 10 | 16 | −37.5% |
| Closed sales | 12 | 17 | −29.4% |
| Median sales price | $1,950,000 | $1,775,000 | +9.9% |
| Inventory of homes for sale | 34 | 31 | +9.7% |
| Months supply of inventory | 2.3 | 2.0 | +15.0% |
| Cumulative days on market until sale | 42 | 36 | +16.7% |
| Percent of original list price received | 95.6% | 99.3% | −3.7% |
| New listings | 13 | 14 | −7.1% |
Year to date through August 2026 compared with Year to date through August 2025
| Metric | Year to date through August 2026 | Year to date through August 2025 | Change |
|---|---|---|---|
| Pending sales | 119 | 130 | −8.5% |
| Closed sales | 121 | 114 | +6.1% |
| Median sales price | $1,750,000 | $1,885,950 | −7.2% |
| Cumulative days on market until sale | 35 | 33 | +6.1% |
| Percent of original list price received | 99.1% | 100.4% | −1.3% |
| New listings | 161 | 184 | −12.5% |
Source: Massachusetts Association of REALTORS® Local Market Update — August 2026, Winchester, Single Family Residence. Data from Berkshire County MLS and Cape Cod & Islands Association of REALTORS®, Inc. and MLS Property Information Network, Inc.. View the Winchester report or browse the Massachusetts Association of REALTORS® report library.
Median sales price and percent of original list price received do not account for seller concessions.
Activity for one month can look extreme because of small sample sizes. Changes in the mix of homes sold can affect the median; it is not a measure of any individual home’s change in value.
These are published August 2026 single-family statistics, not live listing counts. Unreported percentage changes are shown as a dash.
Data provided by the Massachusetts Association of REALTORS®. Report copyright ShowingTime Plus, LLC.