What stands out worked out from the figures below

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

Cheshire has grown the fastest since 2010 (+0.7%).

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	Cheshire
People
Population	1,065Lowest	3,216Highest
Growth since 20102010 → 2020 census	-7.6%Lowest MA: +7.4%	+0.7%Highest MA: +7.4%
Median age	44.8±6.4Lowest 12% above MA	53.7±4.5Highest 34% above MA
	Cheshire and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	15.8%±5.1Highest MA: 19.4%	15.3%±4.2Lowest MA: 19.4%
	Windsor and Cheshire 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%	30.5%±7.1Highest MA: 17.9%
	Cheshire and Windsor 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%	26.9%Lowest MA: 47.3%
Enrolled in collegeshare of residents	2.7%±1.7Lowest MA: 7.9%	5%±2.5Highest MA: 7.9%
	Cheshire and Windsor 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	$69,803±$14kLowest 33% below MA
Home valuemedian, owner-occupied	$389,700±$32kHighest 31% below MA	$268,200±$48kLowest 52% below MA
Property taxmedian, yearly	$3,867Highest 35% below MA	$3,005Lowest 50% below MA
Renters paying 30%+of income on rent	0%±100Lowest MA: 51.8%	21.2%±24Highest MA: 51.8%
	Cheshire 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%	8.6%Highest MA: 10%
Housing
Homeownersof occupied homes	96.2%Highest MA: 62.5%	89%Lowest MA: 62.5%
Typical home builtmedian year	1970Highest 6 yrs newer than MA	1964Lowest same as MA
Getting to work
Average commuteone way	37 minHighest 27% above MA	29 minLowest about the MA average
Work from home	21.2%±5.8Highest MA: 18.6%	4.4%±2.7Lowest MA: 18.6%
Schools
Public school scoresrank in state, math + reading	—	#274 of 282 in MA
School district	—	Hoosac Valley Regional
High school in town	—	Hoosac Valley High School
Students per teacherat that high school	—	10.5
On TownTapestry
Old photos in Our Story	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.