Compare towns
Windsor vs Wellesley 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 homeowners (96.2%).
Wellesley has grown the fastest since 2010 (+5.6%).
Cheshire has the most affordable homes ($268k median).
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 | Wellesley | Cheshire |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 1,065Lowest |
30,347Highest |
3,216 |
| Growth since 20102010 → 2020 census | -7.6%Lowest MA: +7.4% |
+5.6%Highest MA: +7.4% |
+0.7% MA: +7.4% |
| Median age | 44.8±6.4 12% above MA |
37.1±2.2Lowest 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% |
24.1%±2Highest MA: 19.4% |
15.3%±4.2Lowest MA: 19.4% |
| Age 65+ | 18.6%±4.9 MA: 17.9% |
15.5%±1.3Lowest 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% MA: 47.3% |
89%Highest MA: 47.3% |
26.9%Lowest MA: 47.3% |
| Enrolled in collegeshare of residents | 2.7%±1.7Lowest MA: 7.9% |
18.3%±0.7Highest MA: 7.9% |
5%±2.5 MA: 7.9% |
| Cost of living | |||
| Household incomemedian | $115,563±$10k 11% above MA |
$250,001Highest 140% above MA |
$69,803±$14kLowest 33% below MA |
| Home valuemedian, owner-occupied | $389,700±$32k 31% below MA |
$1,582,700±$49kHighest 182% above MA |
$268,200±$48kLowest 52% below MA |
| Rentmedian gross, monthly | — | $2,886±$360 64% above MA |
— |
| Property taxmedian, yearly | $3,867 35% below MA |
$10,000+Highest at least 67% above MA |
$3,005Lowest 50% below MA |
| Renters paying 30%+of income on rent | 0%±100Lowest MA: 51.8% |
44.1%±8.2Highest MA: 51.8% |
21.2%±24 MA: 51.8% |
| Wellesley 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% |
4% MA: 10% |
8.6%Highest MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 96.2%Highest MA: 62.5% |
84.4%Lowest MA: 62.5% |
89% MA: 62.5% |
| Typical home builtmedian year | 1970Highest 6 yrs newer than MA |
1955Lowest 9 yrs older than MA |
1964 same as MA |
| Getting to work | |||
| Average commuteone way | 37 minHighest 27% above MA |
27 minLowest 7% below MA |
29 min about the MA average |
| Work from home | 21.2%±5.8 MA: 18.6% |
32%±2.9Highest MA: 18.6% |
4.4%±2.7Lowest MA: 18.6% |
| Schools | |||
| Public school scoresrank in state, math + reading | — | #6 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.