MARKET INTELLIGENCE
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Monthly data through · Month to date
The average asking price for Winchester was $1,631,111 in October 2026, down 15.7% from October 2025. There were 100 active listings in Winchester during October 2026, down 1.0% from October 2025.
October 2025–November 2026 · November 2026 is month to date
Oct 2026
The average asking price for Winchester was $1,631,111 in October 2026, down 15.7% from October 2025.
| Date | Value |
|---|---|
| 2025-10 | $1,933,927 |
| 2025-11 | $1,896,837 |
| 2025-12 | $1,810,859 |
| 2026-01 | $1,752,338 |
| 2026-02 | $1,651,858 |
| 2026-03 | $1,895,685 |
| 2026-04 | $1,905,093 |
| 2026-05 | $1,903,840 |
| 2026-06 | $1,837,439 |
| 2026-07 | $1,688,209 |
| 2026-08 | $1,707,176 |
| 2026-09 | $1,656,990 |
| 2026-10 | $1,631,111 |
| 2026-11 | $1,613,689 |
Oct 2026
There were 100 active listings in Winchester during October 2026, down 1.0% from October 2025.
| Date | Value |
|---|---|
| 2025-10 | 101 |
| 2025-11 | 99 |
| 2025-12 | 84 |
| 2026-01 | 66 |
| 2026-02 | 60 |
| 2026-03 | 66 |
| 2026-04 | 86 |
| 2026-05 | 107 |
| 2026-06 | 113 |
| 2026-07 | 108 |
| 2026-08 | 84 |
| 2026-09 | 96 |
| 2026-10 | 100 |
| 2026-11 | 96 |
October 2025–November 2026 · November 2026 is month to date
Oct 2026
The average time on market for Winchester was 56.6 days in October 2026, up 42.2% from October 2025.
| Date | Value |
|---|---|
| 2025-10 | 39.8 days |
| 2025-11 | 45 days |
| 2025-12 | 47.4 days |
| 2026-01 | 44.8 days |
| 2026-02 | 37.5 days |
| 2026-03 | 35.9 days |
| 2026-04 | 31.5 days |
| 2026-05 | 28.7 days |
| 2026-06 | 36.3 days |
| 2026-07 | 41.2 days |
| 2026-08 | 57.3 days |
| 2026-09 | 52.8 days |
| 2026-10 | 56.6 days |
| 2026-11 | 60.8 days |
Oct 2026
The average asking price per square foot for Winchester was $550 in October 2026, up 0.5% from October 2025.
| Date | Value |
|---|---|
| 2025-10 | $548 / sq ft |
| 2025-11 | $553 / sq ft |
| 2025-12 | $557 / sq ft |
| 2026-01 | $533 / sq ft |
| 2026-02 | $546 / sq ft |
| 2026-03 | $544 / sq ft |
| 2026-04 | $554 / sq ft |
| 2026-05 | $544 / sq ft |
| 2026-06 | $545 / sq ft |
| 2026-07 | $549 / sq ft |
| 2026-08 | $548 / sq ft |
| 2026-09 | $557 / sq ft |
| 2026-10 | $550 / sq ft |
| 2026-11 | $548 / sq ft |
Observed November 9, 2026
As of Nov 9, 2026
On Nov 9, 2026, 54.4% of active listings with a known listing age in Winchester had been listed for at least 60 days.
Based on 57 observed active listings with a known listing age.
October 2025–November 2026 · November 2026 is month to date
Choose one or more bedroom counts to compare. Each series shows how many ZIPs report that figure.
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | $962,560 |
| Nov 2025 | $898,780 |
| Dec 2025 | $802,816 |
| Jan 2026 | $663,233 |
| Feb 2026 | $645,880 |
| Mar 2026 | Unavailable |
| Apr 2026 | $851,000 |
| May 2026 | $766,127 |
| Jun 2026 | $786,340 |
| Jul 2026 | $666,267 |
| Aug 2026 | $655,300 |
| Sep 2026 | $757,073 |
| Oct 2026 | $723,067 |
| Nov 2026 | $721,400 |
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | 5 |
| Nov 2025 | 5 |
| Dec 2025 | 6 |
| Jan 2026 | 6 |
| Feb 2026 | 5 |
| Mar 2026 | Unavailable |
| Apr 2026 | 8 |
| May 2026 | 11 |
| Jun 2026 | 10 |
| Jul 2026 | 9 |
| Aug 2026 | 8 |
| Sep 2026 | 11 |
| Oct 2026 | 12 |
| Nov 2026 | 12 |
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | 22.4 days |
| Nov 2025 | 29.4 days |
| Dec 2025 | 38 days |
| Jan 2026 | 47.3 days |
| Feb 2026 | 49.6 days |
| Mar 2026 | Unavailable |
| Apr 2026 | 18 days |
| May 2026 | 25 days |
| Jun 2026 | 40.7 days |
| Jul 2026 | 48.1 days |
| Aug 2026 | 73.4 days |
| Sep 2026 | 61.1 days |
| Oct 2026 | 78.6 days |
| Nov 2026 | 86 days |
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | $632 / sq ft |
| Nov 2025 | $623 / sq ft |
| Dec 2025 | $629 / sq ft |
| Jan 2026 | $542 / sq ft |
| Feb 2026 | $530 / sq ft |
| Mar 2026 | Unavailable |
| Apr 2026 | $566 / sq ft |
| May 2026 | $550 / sq ft |
| Jun 2026 | $583 / sq ft |
| Jul 2026 | $598 / sq ft |
| Aug 2026 | $609 / sq ft |
| Sep 2026 | $652 / sq ft |
| Oct 2026 | $611 / sq ft |
| Nov 2026 | $610 / sq ft |
INDEPENDENT LISTING-ACTIVITY RANKING
Winchester · published edition · cutoff Oct 27, 2026
Each figure retains its observation period. Monthly listing counts describe activity during the month; asking prices are not completed sale prices.
City historical prices are listing-count-weighted averages across associated ZIPs.
Cribber. Winchester, MA real estate market. Retrieved November 9, 2026. https://cribber.ai/market-intelligence/winchester