What stands out worked out from the figures below

Dover has the most expensive homes ($1340k median).

Windsor has the most affordable homes ($305k 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	Dover	Windsor
People
Population	5,930Lowest	29,468Highest
Growth since 20102010 → 2020 census	+6% U.S.: +7.4%	—
Median age	44.9±2.3Highest 15% above U.S.	43.7±1.9Lowest 12% above U.S.
	Dover and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	26%±5.2Highest U.S.: 22%	19.2%±2.1Lowest U.S.: 22%
	Dover and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	16.7%±2.9Lowest U.S.: 17.2%	20%±2Highest U.S.: 17.2%
	Windsor and Dover are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	84.8%Highest U.S.: 35.7%	43.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	7.2%±2.7Highest U.S.: 6.4%	5.9%±1.3Lowest U.S.: 6.4%
	Dover and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$250,001Highest 210% above U.S.	$104,725±$8kLowest 30% above U.S.
Home valuemedian, owner-occupied	$1,340,300±$117kHighest 303% above U.S.	$305,200±$11kLowest 8% below U.S.
Rentmedian gross, monthly	$2,917±$2kHighest 106% above U.S.	$1,681±$62Lowest 19% above U.S.
	Dover and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$10,000+Highest at least 221% above U.S.	$5,351Lowest 72% above U.S.
Renters paying 30%+of income on rent	20%±100Lowest U.S.: 51.1%	44.9%±10.9Highest U.S.: 51.1%
	Windsor and Dover are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	2.7%Lowest U.S.: 12.5%	6.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	97.9%Highest U.S.: 65.2%	82.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1970 10 yrs older than U.S.	1970 10 yrs older than U.S.
Getting to work
Average commuteone way	35 minHighest 31% above U.S.	21 minLowest 19% below U.S.
Work from home	34.2%±6.4Highest U.S.: 15.1%	16.1%±3.2Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#1 of 282 in MA	#117 of 149 in CT
School district	Dover · Dover-Sherborn	Capitol Region Education Council · Windsor School District
High school in town	Dover-Sherborn Regional High	Windsor High School
Students per teacherat that high school	9.8Lowest	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.