What stands out worked out from the figures below

Canton has the most expensive homes ($711k median).

Windsor has the most affordable homes ($305k 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	Canton	Windsor
People
Population	24,748Lowest	29,468Highest
Growth since 20102010 → 2020 census	+13% U.S.: +7.4%	—
Median age	42.6±2.3Lowest 10% above U.S.	43.7±1.9Highest 12% above U.S.
	Windsor and Canton are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	22.9%±2.3Highest U.S.: 22%	19.2%±2.1Lowest U.S.: 22%
	Canton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.8%±2Lowest U.S.: 17.2%	20%±2Highest U.S.: 17.2%
	Windsor and Canton are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	67.5%Highest U.S.: 35.7%	43.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.5%±1Lowest U.S.: 6.4%	5.9%±1.3Highest U.S.: 6.4%
	Windsor and Canton are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$143,381±$9kHighest 78% above U.S.	$104,725±$8kLowest 30% above U.S.
Home valuemedian, owner-occupied	$710,600±$27kHighest 114% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$2,315±$178Highest 64% above U.S.	$1,681±$62Lowest 19% above U.S.
Property taxmedian, yearly	$6,560Highest 110% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	52.4%±9.1Highest U.S.: 51.1%	44.9%±10.9Lowest U.S.: 51.1%
	Canton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	5.2%Lowest U.S.: 12.5%	6.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	73.6%Lowest U.S.: 65.2%	82.4%Highest U.S.: 65.2%
Typical home builtmedian year	1980Highest same as U.S.	1970Lowest 10 yrs older than U.S.
Getting to work
Average commuteone way	36 minHighest 36% above U.S.	21 minLowest 19% below U.S.
Work from home	25.7%±3.3Highest U.S.: 15.1%	16.1%±3.2Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#81 of 282 in MA	#117 of 149 in CT
School district	Blue Hills Regional Vocational Technical · Canton	Capitol Region Education Council · Windsor School District
High school in town	Canton High	Windsor High School
Students per teacherat that high school	13.1Highest	10.2Lowest
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.