Winchester, MA housing market
The typical Winchester home is worth about $1,549,000, up 2.4% in a year, 134% above the Massachusetts typical home. Homes typically sell in 16 days, a little above asking.
Home values, sales, trends and how Winchester compares with the towns next door — updated as new data is published.
Winchester at a glance
A strong seller's market
Homes are selling faster than new ones are listed: less than two months of supply. Well-priced homes can draw several offers.
Typical home value, 2016–2026
Show as a table
| January | Winchester | Massachusetts |
|---|---|---|
| 2017 | $970,000 | $382,000 |
| 2018 | $1,009,000 | $407,000 |
| 2019 | $1,050,000 | $426,000 |
| 2020 | $1,050,000 | $438,000 |
| 2021 | $1,129,000 | $485,000 |
| 2022 | $1,244,000 | $536,000 |
| 2023 | $1,318,000 | $572,000 |
| 2024 | $1,444,000 | $616,000 |
| 2025 | $1,507,000 | $648,000 |
| 2026 | $1,542,000 | $658,000 |
| August 2026 | $1,549,000 | $662,000 |
Winchester and its neighbors
6.7 years of income
The typical Winchester home costs about 6.7 years of the town's median household income, more than across Massachusetts (6.4 years).
How Winchester ranks on affordability →
Home value ÷ ACS median household income.
Owners, rent & taxes
U.S. Census Bureau, ACS 2020-2024.
Recent listings in Winchester
Home values: Zillow Home Value Index (ZHVI), Zillow Research, August 2026. Sales, days on market and supply: Redfin Data Center, May 2026. Income, ownership, taxes and rent: U.S. Census Bureau, American Community Survey. Listings link to their publishers.