What stands out worked out from the figures below

Sturbridge has the most expensive homes ($426k median).

Windsor has the shortest commute (21 min average).

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	Sturbridge	Windsor
People
Population	9,960Lowest	29,468Highest
Growth since 20102010 → 2020 census	+6.5% U.S.: +7.4%	—
Median age	47.2±2.6Highest 21% above U.S.	43.7±1.9Lowest 12% above U.S.
	Sturbridge and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	20.7%±3Highest U.S.: 22%	19.2%±2.1Lowest U.S.: 22%
	Sturbridge and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	19.8%±3Lowest U.S.: 17.2%	20%±2Highest U.S.: 17.2%
	Windsor and Sturbridge are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	49.3%Highest U.S.: 35.7%	43.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.6%±1.5Lowest U.S.: 6.4%	5.9%±1.3Highest U.S.: 6.4%
	Windsor and Sturbridge are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$136,759±$15kHighest 69% above U.S.	$104,725±$8kLowest 30% above U.S.
Home valuemedian, owner-occupied	$425,800±$18kHighest 28% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$1,193±$398Lowest 16% below U.S.	$1,681±$62Highest 19% above U.S.
Property taxmedian, yearly	$6,520Highest 109% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	42%±17.7Lowest U.S.: 51.1%	44.9%±10.9Highest U.S.: 51.1%
	Windsor and Sturbridge are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	3.7%Lowest U.S.: 12.5%	6.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	86.3%Highest U.S.: 65.2%	82.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1982Highest 2 yrs newer than U.S.	1970Lowest 10 yrs older than U.S.
Getting to work
Average commuteone way	38 minHighest 43% above U.S.	21 minLowest 19% below U.S.
Work from home	19.8%±4.8Highest U.S.: 15.1%	16.1%±3.2Lowest U.S.: 15.1%
	Sturbridge 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	#89 of 282 in MA	#117 of 149 in CT
School district	Sturbridge · Tantasqua	Capitol Region Education Council · Windsor School District
High school in town	Tantasqua Regional Sr High	Windsor High School
Students per teacherat that high school	7.7Lowest	10.2Highest
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.