What stands out worked out from the figures below

Wilbraham has the most people working from home (12.9%).

Winchester has the most affordable homes ($250k 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	Winchester
People
Population	14,572Highest	10,284Lowest
Growth since 20102010 → 2020 census	+2.8% U.S.: +7.4%	—
Median age	44.3±2.7Lowest 14% above U.S.	49.1±6.2Highest 26% above U.S.
	Winchester and Wilbraham 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%	15.4%±2.9Lowest U.S.: 22%
Age 65+	23%±3.4Lowest U.S.: 17.2%	27.4%±5.1Highest U.S.: 17.2%
	Winchester and Wilbraham 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%	27.8%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.2%±1.8Highest U.S.: 6.4%	4.2%±1.7Lowest U.S.: 6.4%
	Wilbraham and Winchester 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.	$66,519±$12kLowest 18% below U.S.
Home valuemedian, owner-occupied	$416,000±$25kHighest 25% above U.S.	$249,500±$17kLowest 25% below U.S.
Rentmedian gross, monthly	$1,175±$241Highest 17% below U.S.	$1,174±$116Lowest 17% below U.S.
	Wilbraham and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,658Highest 113% above U.S.	$4,780Lowest 53% above U.S.
Renters paying 30%+of income on rent	53.1%±23.8Highest U.S.: 51.1%	48.9%±15.8Lowest U.S.: 51.1%
	Wilbraham and Winchester 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%	12.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	88.8%Highest U.S.: 65.2%	65.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1966Highest 14 yrs older than U.S.	1955Lowest 25 yrs older than U.S.
Getting to work
Average commuteone way	27 minHighest about the U.S. average	26 minLowest about the U.S. average
Work from home	12.9%±3.1Highest U.S.: 15.1%	6.9%±2.7Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#88 of 282 in MA	#97 of 149 in CT
School district	Hampden-Wilbraham	Explorations District · Regional School District 07
High school in town	Minnechaug Regional High	Northwestern Regional High School
Students per teacherat that high school	14.2Highest	9.7Lowest
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.