What stands out worked out from the figures below

Windsor has the shortest commute (21 min average).

Sturbridge has the most expensive homes ($426k 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	Sturbridge
People
Population	29,468Highest	9,960Lowest
Growth since 20102010 → 2020 census	—	+6.5% U.S.: +7.4%
Median age	43.7±1.9Lowest 12% above U.S.	47.2±2.6Highest 21% 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	19.2%±2.1Lowest U.S.: 22%	20.7%±3Highest 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+	20%±2Highest U.S.: 17.2%	19.8%±3Lowest 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+	43.2%Lowest U.S.: 35.7%	49.3%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.9%±1.3Highest U.S.: 6.4%	4.6%±1.5Lowest 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	$104,725±$8kLowest 30% above U.S.	$136,759±$15kHighest 69% above U.S.
Home valuemedian, owner-occupied	$305,200±$11kLowest 8% below U.S.	$425,800±$18kHighest 28% above U.S.
Rentmedian gross, monthly	$1,681±$62Highest 19% above U.S.	$1,193±$398Lowest 16% below U.S.
Property taxmedian, yearly	$5,351Lowest 72% above U.S.	$6,520Highest 109% above U.S.
Renters paying 30%+of income on rent	44.9%±10.9Highest U.S.: 51.1%	42%±17.7Lowest 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	6.7%Highest U.S.: 12.5%	3.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	82.4%Lowest U.S.: 65.2%	86.3%Highest U.S.: 65.2%
Typical home builtmedian year	1970Lowest 10 yrs older than U.S.	1982Highest 2 yrs newer than U.S.
Getting to work
Average commuteone way	21 minLowest 19% below U.S.	38 minHighest 43% above U.S.
Work from home	16.1%±3.2Lowest U.S.: 15.1%	19.8%±4.8Highest 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	#117 of 149 in CT	#89 of 282 in MA
School district	Capitol Region Education Council · Windsor School District	Sturbridge · Tantasqua
High school in town	Windsor High School	Tantasqua Regional Sr High
Students per teacherat that high school	10.2Highest	7.7Lowest
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.