What stands out worked out from the figures below

Windsor has the most affordable homes ($390k median).

Chilmark has grown the fastest since 2010 (+40%).

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	1,065Lowest	1,578Highest
Growth since 20102010 → 2020 census	-7.6%Lowest MA: +7.4%	+40%Highest MA: +7.4%
Median age	44.8±6.4Lowest 12% above MA	53.6±8.1Highest 34% above MA
	Chilmark and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	15.8%±5.1Lowest MA: 19.4%	16.7%±4.3Highest MA: 19.4%
	Chilmark and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.6%±4.9Lowest MA: 17.9%	36.2%±12.4Highest MA: 17.9%
Bachelor’s degree+adults 25+	41.5%Lowest MA: 47.3%	68.1%Highest MA: 47.3%
Enrolled in collegeshare of residents	2.7%±1.7 MA: 7.9%	2.7%±2.6 MA: 7.9%
Cost of living
Household incomemedian	$115,563±$10kLowest 11% above MA	$168,750±$28kHighest 62% above MA
Home valuemedian, owner-occupied	$389,700±$32kLowest 31% below MA	$1,895,300±$281kHighest 237% above MA
Rentmedian gross, monthly	—	$2,750±$2k 56% above MA
Property taxmedian, yearly	$3,867Lowest 35% below MA	$4,485Highest 25% below MA
Renters paying 30%+of income on rent	0%±100Lowest MA: 51.8%	30.8%±59.9Highest MA: 51.8%
	Chilmark and Windsor 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%	4.1%Highest MA: 10%
Housing
Homeownersof occupied homes	96.2%Highest MA: 62.5%	89.4%Lowest MA: 62.5%
Typical home builtmedian year	1970Lowest 6 yrs newer than MA	1984Highest 20 yrs newer than MA
Getting to work
Average commuteone way	37 minHighest 27% above MA	32 minLowest 8% above MA
Work from home	21.2%±5.8Lowest MA: 18.6%	25.7%±11Highest MA: 18.6%
	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

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.