What stands out worked out from the figures below

Windsor has the most affordable homes ($305k median).

Upton has the most expensive homes ($577k 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	Windsor	Upton
People
Population	29,468Highest	8,189Lowest
Growth since 20102010 → 2020 census	—	+6.1% U.S.: +7.4%
Median age	43.7±1.9Lowest 12% above U.S.	46.4±4.8Highest 19% above U.S.
	Upton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.2%±2.1Lowest U.S.: 22%	23.2%±4.5Highest U.S.: 22%
	Upton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	20%±2Lowest U.S.: 17.2%	20.7%±4.9Highest U.S.: 17.2%
	Upton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	43.2%Lowest U.S.: 35.7%	53.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.9%±1.3Highest U.S.: 6.4%	2.4%±1.3Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$104,725±$8kLowest 30% above U.S.	$155,508±$33kHighest 93% above U.S.
Home valuemedian, owner-occupied	$305,200±$11kLowest 8% below U.S.	$576,700±$41kHighest 73% above U.S.
Rentmedian gross, monthly	$1,681±$62Highest 19% above U.S.	$948±$599Lowest 33% below U.S.
Property taxmedian, yearly	$5,351Lowest 72% above U.S.	$8,376Highest 169% above U.S.
Renters paying 30%+of income on rent	44.9%±10.9Lowest U.S.: 51.1%	52.8%±31Highest U.S.: 51.1%
	Upton and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	6.7%Highest U.S.: 12.5%	3.2%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	82.4%Lowest U.S.: 65.2%	86.7%Highest U.S.: 65.2%
Typical home builtmedian year	1970Lowest 10 yrs older than U.S.	1981Highest 1 yr newer than U.S.
Getting to work
Average commuteone way	21 minLowest 19% below U.S.	35 minHighest 34% above U.S.
Work from home	16.1%±3.2Lowest U.S.: 15.1%	22.8%±5.3Highest U.S.: 15.1%
	Upton and Windsor 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	#117 of 149 in CT	#46 of 282 in MA
School district	Capitol Region Education Council · Windsor School District	Blackstone Valley Regional Vocational Technical · Mendon-Upton
High school in town	Windsor High School	Blackstone Valley
Students per teacherat that high school	10.2Lowest	11.2Highest
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.