What stands out worked out from the figures below

Windham has the most affordable homes ($210k median).

Upton has the most people working from home (22.8%).

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	Windham	Upton
People
Population	23,961Highest	8,189Lowest
Growth since 20102010 → 2020 census	—	+6.1% U.S.: +7.4%
Median age	33.7±1.9Lowest 13% below U.S.	46.4±4.8Highest 19% above U.S.
Kids under 18	20.1%±2.4Lowest U.S.: 22%	23.2%±4.5Highest U.S.: 22%
	Upton and Windham are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	14.3%±1.9Lowest U.S.: 17.2%	20.7%±4.9Highest U.S.: 17.2%
	Upton and Windham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	22.7%Lowest U.S.: 35.7%	53.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	15.2%±1.8Highest U.S.: 6.4%	2.4%±1.3Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$55,736±$5kLowest 31% below U.S.	$155,508±$33kHighest 93% above U.S.
Home valuemedian, owner-occupied	$209,800±$9kLowest 37% below U.S.	$576,700±$41kHighest 73% above U.S.
Rentmedian gross, monthly	$1,107±$69Highest 22% below U.S.	$948±$599Lowest 33% below U.S.
	Windham and Upton are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$4,633Lowest 49% above U.S.	$8,376Highest 169% above U.S.
Renters paying 30%+of income on rent	57.1%±8.1Highest U.S.: 51.1%	52.8%±31Lowest U.S.: 51.1%
	Windham and Upton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	20.7%Highest U.S.: 12.5%	3.2%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	47.4%Lowest U.S.: 65.2%	86.7%Highest U.S.: 65.2%
Typical home builtmedian year	1956Lowest 24 yrs older than U.S.	1981Highest 1 yr newer than U.S.
Getting to work
Average commuteone way	24 minLowest 8% below U.S.	35 minHighest 34% above U.S.
Work from home	6.1%±1.7Lowest U.S.: 15.1%	22.8%±5.3Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#143 of 149 in CT	#46 of 282 in MA
School district	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS	Blackstone Valley Regional Vocational Technical · Mendon-Upton
High school in town	Windham High School	Blackstone Valley
Students per teacherat that high school	9.8Lowest	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.