Compare towns
Chilmark vs Dover vs Winchester
Cost, people, housing, commute and schools, side by side, each benchmarked against Massachusetts.
What stands out worked out from the figures below
Chilmark has grown the fastest since 2010 (+40%).
Dover has the most people working from home (37.4%).
Winchester has the most kids (27.6% under 18).
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 | Chilmark | Dover | Winchester |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 1,578Lowest |
2,308 |
23,406Highest |
| Growth since 20102010 → 2020 census | +40%Highest MA: +7.4% |
+8.3% MA: +7.4% |
+7.5%Lowest MA: +7.4% |
| Median age | 53.6±8.1Highest 34% above MA |
47.5±4 19% above MA |
42.5±1.9Lowest 6% above MA |
| Chilmark and Dover are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 16.7%±4.3Lowest MA: 19.4% |
20.9%±4.8 MA: 19.4% |
27.6%±2.3Highest MA: 19.4% |
| Winchester and Dover are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 36.2%±12.4Highest MA: 17.9% |
15.5%±3.5Lowest MA: 17.9% |
18%±2 MA: 17.9% |
| Bachelor’s degree+adults 25+ | 68.1%Lowest MA: 47.3% |
83.4%Highest MA: 47.3% |
79.5% MA: 47.3% |
| Enrolled in collegeshare of residents | 2.7%±2.6Lowest MA: 7.9% |
9.4%±4.8Highest MA: 7.9% |
4.9%±1.3 MA: 7.9% |
| Dover and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $168,750±$28kLowest 62% above MA |
$250,001Highest 140% above MA |
$230,198±$21k 121% above MA |
| Home valuemedian, owner-occupied | $1,895,300±$281kHighest 237% above MA |
$1,308,300±$149k 133% above MA |
$1,215,200±$39kLowest 116% above MA |
| Rentmedian gross, monthly | $2,750±$2kHighest 56% above MA |
— | $2,279±$481Lowest 29% above MA |
| Chilmark and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Property taxmedian, yearly | $4,485Lowest 25% below MA |
$10,000+Highest at least 67% above MA |
$10,000+Highest at least 67% above MA |
| Renters paying 30%+of income on rent | 30.8%±59.9Lowest MA: 51.8% |
100%±100Highest MA: 51.8% |
39.3%±13.3 MA: 51.8% |
| Dover and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 4.1% MA: 10% |
3.3%Lowest MA: 10% |
4.7%Highest MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 89.4% MA: 62.5% |
97.9%Highest MA: 62.5% |
81.7%Lowest MA: 62.5% |
| Typical home builtmedian year | 1984Highest 20 yrs newer than MA |
1967 3 yrs newer than MA |
1954Lowest 10 yrs older than MA |
| Getting to work | |||
| Average commuteone way | 32 min 8% above MA |
37 minHighest 26% above MA |
31 minLowest 8% above MA |
| Work from home | 25.7%±11Lowest MA: 18.6% |
37.4%±8.8Highest MA: 18.6% |
33.8%±3 MA: 18.6% |
| Dover and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Schools | |||
| Public school scoresrank in state, math + reading | — | #1 of 282 in MA | #11 of 282 in MA |
| School district | Up-Island Regional | — | Winchester |
| High school in town | None in town | — | Winchester High School |
| Students per teacherat that high school | — | — | 14.8 |
| 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.