What stands out worked out from the figures below

Winchester has the most kids (27.6% under 18).

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	Winchester	Chilmark
People
Population	23,406Highest	1,578Lowest
Growth since 20102010 → 2020 census	+7.5%Lowest MA: +7.4%	+40%Highest MA: +7.4%
Median age	42.5±1.9Lowest 6% above MA	53.6±8.1Highest 34% above MA
Kids under 18	27.6%±2.3Highest MA: 19.4%	16.7%±4.3Lowest MA: 19.4%
Age 65+	18%±2Lowest MA: 17.9%	36.2%±12.4Highest MA: 17.9%
Bachelor’s degree+adults 25+	79.5%Highest MA: 47.3%	68.1%Lowest MA: 47.3%
Enrolled in collegeshare of residents	4.9%±1.3Highest MA: 7.9%	2.7%±2.6Lowest MA: 7.9%
	Winchester and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$230,198±$21kHighest 121% above MA	$168,750±$28kLowest 62% above MA
Home valuemedian, owner-occupied	$1,215,200±$39kLowest 116% above MA	$1,895,300±$281kHighest 237% above MA
Rentmedian gross, monthly	$2,279±$481Lowest 29% above MA	$2,750±$2kHighest 56% 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	$10,000+Highest at least 67% above MA	$4,485Lowest 25% below MA
Renters paying 30%+of income on rent	39.3%±13.3Highest MA: 51.8%	30.8%±59.9Lowest MA: 51.8%
	Winchester and Chilmark are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.7%Highest MA: 10%	4.1%Lowest MA: 10%
Housing
Homeownersof occupied homes	81.7%Lowest MA: 62.5%	89.4%Highest MA: 62.5%
Typical home builtmedian year	1954Lowest 10 yrs older than MA	1984Highest 20 yrs newer than MA
Getting to work
Average commuteone way	31 minLowest 8% above MA	32 minHighest 8% above MA
Work from home	33.8%±3Highest MA: 18.6%	25.7%±11Lowest MA: 18.6%
	Winchester and Chilmark 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	#11 of 282 in MA	—
School district	Winchester	Up-Island Regional
High school in town	Winchester High School	None in town
Students per teacherat that high school	14.8	—
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.