What stands out worked out from the figures below

Windsor has the most affordable homes ($338k median).

Chilmark has the most expensive homes ($1895k 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.

Raising kidsAffordabilityOwning a homeShort commuteWorking from homeYounger crowdSettled, older crowdGrowing town

Measure	Windsor	Chilmark
People
Population	254Lowest	1,578Highest
Growth since 20102010 → 2020 census	—	+40% U.S.: +7.4%
Median age	40.2±18.8Lowest 3% above U.S.	53.6±8.1Highest 38% above U.S.
	Chilmark and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	25.2%±14.7Highest U.S.: 22%	16.7%±4.3Lowest U.S.: 22%
	Windsor and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	15.7%±8Lowest U.S.: 17.2%	36.2%±12.4Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	12.6%Lowest U.S.: 35.7%	68.1%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	3.9%±4.2Highest U.S.: 6.4%	2.7%±2.6Lowest U.S.: 6.4%
	Windsor and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$103,750±$40kLowest 29% above U.S.	$168,750±$28kHighest 109% above U.S.
	Chilmark and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$337,500±$40kLowest about the U.S. average	$1,895,300±$281kHighest 470% above U.S.
Rentmedian gross, monthly	—	$2,750±$2k 95% above U.S.
Property taxmedian, yearly	$3,381Lowest 8% above U.S.	$4,485Highest 44% above U.S.
Renters paying 30%+of income on rent	66.7%±100Highest U.S.: 51.1%	30.8%±59.9Lowest U.S.: 51.1%
	Windsor and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	10.8%Highest U.S.: 12.5%	4.1%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	96.5%Highest U.S.: 65.2%	89.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1983Lowest 3 yrs newer than U.S.	1984Highest 4 yrs newer than U.S.
Getting to work
Average commuteone way	32 minHighest 22% above U.S.	32 minLowest 19% above U.S.
Work from home	15%±16.5Lowest U.S.: 15.1%	25.7%±11Highest U.S.: 15.1%
	Chilmark and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Schools
School district	—	Up-Island Regional
High school in town	—	None in town
On TownTapestry
Old photos in History	None yet	None yet

U.S. 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.