Compare towns
Windsor vs Webster vs Cheshire
Cost, people, housing, commute and schools, side by side, each benchmarked against Massachusetts.
What stands out worked out from the figures below
Windsor has the most people working from home (21.2%).
Webster has grown the fastest since 2010 (+6.9%).
Cheshire has the oldest population (median age 53.7).
What matters to you?
Pick a few. We’ll pull those rows to the top and mark which town comes out ahead on each. There’s no overall score: what matters is up to you.
| Measure | Windsor | Webster | Cheshire |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 1,065Lowest |
12,228Highest |
3,216 |
| Growth since 20102010 → 2020 census | -7.6%Lowest MA: +7.4% |
+6.9%Highest MA: +7.4% |
+0.7% MA: +7.4% |
| Median age | 44.8±6.4 12% above MA |
37.2±2.1Lowest 7% below MA |
53.7±4.5Highest 34% above MA |
| Cheshire and Windsor are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 15.8%±5.1 MA: 19.4% |
21.8%±3.6Highest MA: 19.4% |
15.3%±4.2Lowest MA: 19.4% |
| Webster and Windsor are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 18.6%±4.9 MA: 17.9% |
15.7%±2.5Lowest MA: 17.9% |
30.5%±7.1Highest MA: 17.9% |
| Cheshire and Windsor are within the Census margin of error here, so we can’t say which is really higher. | |||
| Bachelor’s degree+adults 25+ | 41.5%Highest MA: 47.3% |
18.8%Lowest MA: 47.3% |
26.9% MA: 47.3% |
| Enrolled in collegeshare of residents | 2.7%±1.7Lowest MA: 7.9% |
6%±1.8Highest MA: 7.9% |
5%±2.5 MA: 7.9% |
| Webster and Cheshire are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $115,563±$10kHighest 11% above MA |
$63,837±$8kLowest 39% below MA |
$69,803±$14k 33% below MA |
| Home valuemedian, owner-occupied | $389,700±$32kHighest 31% below MA |
$333,100±$14k 41% below MA |
$268,200±$48kLowest 52% below MA |
| Rentmedian gross, monthly | — | $1,198±$85 32% below MA |
— |
| Property taxmedian, yearly | $3,867Highest 35% below MA |
$3,234 46% below MA |
$3,005Lowest 50% below MA |
| Renters paying 30%+of income on rent | 0%±100Lowest MA: 51.8% |
46.1%±7.4Highest MA: 51.8% |
21.2%±24 MA: 51.8% |
| Webster and Cheshire are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 3.8%Lowest MA: 10% |
16%Highest MA: 10% |
8.6% MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 96.2%Highest MA: 62.5% |
45.5%Lowest MA: 62.5% |
89% MA: 62.5% |
| Typical home builtmedian year | 1970Highest 6 yrs newer than MA |
1954Lowest 10 yrs older than MA |
1964 same as MA |
| Getting to work | |||
| Average commuteone way | 37 minHighest 27% above MA |
28 minLowest 5% below MA |
29 min about the MA average |
| Work from home | 21.2%±5.8Highest MA: 18.6% |
7.1%±2.9 MA: 18.6% |
4.4%±2.7Lowest MA: 18.6% |
| Schools | |||
| Public school scoresrank in state, math + reading | — | #271 of 282 in MA | #274 of 282 in MA |
| School district | — | — | Hoosac Valley Regional |
| High school in town | — | — | Hoosac Valley High School |
| Students per teacherat that high school | — | — | 10.5 |
| On TownTapestry | |||
| Old photos in History | None yet | None yet | None yet |
MA average · Sources: U.S. Census Bureau, American Community Survey 5-year estimates 2020–2024; 2010 & 2020 decennial census; NCES Common Core of Data. “±” is the Census margin of error. Property tax is top-coded by the Census at $10,000+. School rank compares math and reading proficiency against the state average.