Compare towns
Windsor vs Dover 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 youngest population (median age 44.8).
Dover has grown the fastest since 2010 (+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 | Dover | Cheshire |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 1,065Lowest |
5,930Highest |
3,216 |
| Growth since 20102010 → 2020 census | -7.6%Lowest MA: +7.4% |
+6%Highest MA: +7.4% |
+0.7% MA: +7.4% |
| Median age | 44.8±6.4Lowest 12% above MA |
44.9±2.3 12% above MA |
53.7±4.5Highest 34% above MA |
| Kids under 18 | 15.8%±5.1 MA: 19.4% |
26%±5.2Highest MA: 19.4% |
15.3%±4.2Lowest MA: 19.4% |
| Dover 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% |
16.7%±2.9Lowest 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% |
84.8%Highest MA: 47.3% |
26.9%Lowest MA: 47.3% |
| Enrolled in collegeshare of residents | 2.7%±1.7Lowest MA: 7.9% |
7.2%±2.7Highest MA: 7.9% |
5%±2.5 MA: 7.9% |
| Dover 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±$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 |
$1,340,300±$117kHighest 138% above MA |
$268,200±$48kLowest 52% below MA |
| Rentmedian gross, monthly | — | $2,917±$2k 66% 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% |
20%±100 MA: 51.8% |
21.2%±24Highest MA: 51.8% |
| Cheshire and Dover are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 3.8% MA: 10% |
2.7%Lowest MA: 10% |
8.6%Highest MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 96.2% MA: 62.5% |
97.9%Highest MA: 62.5% |
89%Lowest MA: 62.5% |
| Typical home builtmedian year | 1970Highest 6 yrs newer than MA |
1970Highest 6 yrs newer than MA |
1964Lowest same as MA |
| Getting to work | |||
| Average commuteone way | 37 minHighest 27% above MA |
35 min 19% above MA |
29 minLowest about the MA average |
| Work from home | 21.2%±5.8 MA: 18.6% |
34.2%±6.4Highest MA: 18.6% |
4.4%±2.7Lowest MA: 18.6% |
| Schools | |||
| Public school scoresrank in state, math + reading | — | #1 of 282 in MA | #274 of 282 in MA |
| School district | — | Dover · Dover-Sherborn | Hoosac Valley Regional |
| High school in town | — | Dover-Sherborn Regional High | Hoosac Valley High School |
| Students per teacherat that high school | — | 9.8Lowest |
10.5Highest |
| 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.