What stands out worked out from the figures below

Windsor has the most people working from home (21.2%).

Chester has the most kids (24.1% 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.

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

Measure	Windsor	Chester
People
Population	1,065Lowest	1,240Highest
Growth since 20102010 → 2020 census	-7.6%Highest MA: +7.4%	-8.2%Lowest MA: +7.4%
Median age	44.8±6.4Lowest 12% above MA	45.9±3.7Highest 15% above MA
	Chester 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%	24.1%±8.5Highest MA: 19.4%
	Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.6%±4.9Highest MA: 17.9%	16.5%±1.9Lowest MA: 17.9%
	Windsor and Chester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	41.5%Highest MA: 47.3%	27.3%Lowest MA: 47.3%
Enrolled in collegeshare of residents	2.7%±1.7Highest MA: 7.9%	2.4%±1.2Lowest MA: 7.9%
	Windsor and Chester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$115,563±$10kHighest 11% above MA	$89,390±$6kLowest 14% below MA
Home valuemedian, owner-occupied	$389,700±$32kHighest 31% below MA	$281,900±$14kLowest 50% below MA
Rentmedian gross, monthly	—	$1,104±$71 37% below MA
Property taxmedian, yearly	$3,867Lowest 35% below MA	$4,522Highest 25% below MA
Renters paying 30%+of income on rent	0%±100Lowest MA: 51.8%	54.1%±22.6Highest MA: 51.8%
	Chester and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	3.8%Highest MA: 10%	1.8%Lowest MA: 10%
Housing
Homeownersof occupied homes	96.2%Highest MA: 62.5%	82.5%Lowest MA: 62.5%
Typical home builtmedian year	1970Highest 6 yrs newer than MA	1951Lowest 13 yrs older than MA
Getting to work
Average commuteone way	37 minHighest 27% above MA	32 minLowest 9% above MA
Work from home	21.2%±5.8Highest MA: 18.6%	7%±2.7Lowest MA: 18.6%
Schools
School district	—	Gateway
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.