What stands out worked out from the figures below

Wilbraham has the most expensive homes ($416k 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	Wilbraham	Windsor
People
Population	14,572Lowest	29,468Highest
Growth since 20102010 → 2020 census	+2.8% U.S.: +7.4%	—
Median age	44.3±2.7Highest 14% above U.S.	43.7±1.9Lowest 12% above U.S.
	Wilbraham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	23.2%±3.7Highest U.S.: 22%	19.2%±2.1Lowest U.S.: 22%
	Wilbraham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	23%±3.4Highest U.S.: 17.2%	20%±2Lowest U.S.: 17.2%
	Wilbraham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	51.9%Highest U.S.: 35.7%	43.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.2%±1.8Lowest U.S.: 6.4%	5.9%±1.3Highest U.S.: 6.4%
	Windsor and Wilbraham are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$122,051±$14kHighest 51% above U.S.	$104,725±$8kLowest 30% above U.S.
	Wilbraham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$416,000±$25kHighest 25% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$1,175±$241Lowest 17% below U.S.	$1,681±$62Highest 19% above U.S.
Property taxmedian, yearly	$6,658Highest 113% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	53.1%±23.8Highest U.S.: 51.1%	44.9%±10.9Lowest U.S.: 51.1%
	Wilbraham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.6%Lowest U.S.: 12.5%	6.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	88.8%Highest U.S.: 65.2%	82.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1966Lowest 14 yrs older than U.S.	1970Highest 10 yrs older than U.S.
Getting to work
Average commuteone way	27 minHighest about the U.S. average	21 minLowest 19% below U.S.
Work from home	12.9%±3.1Lowest U.S.: 15.1%	16.1%±3.2Highest U.S.: 15.1%
	Windsor and Wilbraham 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	#88 of 282 in MA	#117 of 149 in CT
School district	Hampden-Wilbraham	Capitol Region Education Council · Windsor School District
High school in town	Minnechaug Regional High	Windsor High School
Students per teacherat that high school	14.2Highest	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.