Housing · Windsor
Windsor, MA housing market
The typical Windsor home is worth about $362,000, up 1.4% in a year, 45% below the Massachusetts typical home.
Home values, sales, trends and how Windsor compares with the towns next door — updated as new data is published.
The market right now
Windsor at a glance
Typical home value
$362K
▲ 1.4% in a year · Zillow
Ten-year trend
Typical home value, 2016–2026
WindsorMassachusetts
Show as a table
| January | Windsor | Massachusetts |
|---|---|---|
| 2017 | $189,000 | $382,000 |
| 2018 | $201,000 | $407,000 |
| 2019 | $207,000 | $426,000 |
| 2020 | $220,000 | $438,000 |
| 2021 | $249,000 | $485,000 |
| 2022 | $282,000 | $536,000 |
| 2023 | $317,000 | $572,000 |
| 2024 | $343,000 | $616,000 |
| 2025 | $350,000 | $648,000 |
| 2026 | $355,000 | $658,000 |
| August 2026 | $362,000 | $662,000 |
Next door
Windsor and its neighbors
The towns that share a border. Tap one to see its housing page.
| Town | Typical value | 1-yr change | Days on market | Median income |
|---|---|---|---|---|
| Windsor | $362K | +1.4% | — | $115,563 |
| Cheshire | $363K | +2.4% | — | $69,803 |
| Dalton | $348K | +2.1% | — | $79,438 |
| Plainfield | $326K | +4.2% | — | $63,500 |
| Cummington | $393K | +2.3% | — | $104,167 |
Affordability
3.1 years of income
The typical Windsor home costs about 3.1 years of the town's median household income, less than across Massachusetts (6.4 years).
Home value ÷ ACS median household income.
The homes
Owners, rent & taxes
Homeownership
96.2%
Massachusetts: 62.5%
Median tax bill
$3,867
Massachusetts: $5,992
Typical home built
1970
Massachusetts: 1964
U.S. Census Bureau, ACS 2020-2024.
Home values: Zillow Home Value Index (ZHVI), Zillow Research, August 2026. Sales, days on market and supply: Redfin Data Center. Income, ownership, taxes and rent: U.S. Census Bureau, American Community Survey. Listings link to their publishers.