What stands out worked out from the figures below

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

Dedham has the most expensive homes ($662k 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	Dedham
People
Population	29,468Highest	25,237Lowest
Growth since 20102010 → 2020 census	—	+2.6% U.S.: +7.4%
Median age	43.7±1.9Lowest 12% above U.S.	44.6±1.6Highest 15% above U.S.
	Dedham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.2%±2.1Highest U.S.: 22%	18.6%±1.9Lowest U.S.: 22%
	Windsor and Dedham 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%	21.9%±2Highest U.S.: 17.2%
	Dedham 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%	55%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.9%±1.3Highest U.S.: 6.4%	5.6%±1Lowest U.S.: 6.4%
	Windsor and Dedham 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.	$128,955±$10kHighest 60% above U.S.
Home valuemedian, owner-occupied	$305,200±$11kLowest 8% below U.S.	$661,800±$16kHighest 99% above U.S.
Rentmedian gross, monthly	$1,681±$62Lowest 19% above U.S.	$2,042±$182Highest 45% above U.S.
Property taxmedian, yearly	$5,351Lowest 72% above U.S.	$7,918Highest 154% above U.S.
Renters paying 30%+of income on rent	44.9%±10.9Lowest U.S.: 51.1%	56.4%±10Highest U.S.: 51.1%
	Dedham 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%	5.6%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	82.4%Highest U.S.: 65.2%	73.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1970Highest 10 yrs older than U.S.	1956Lowest 24 yrs older than U.S.
Getting to work
Average commuteone way	21 minLowest 19% below U.S.	29 minHighest 11% above U.S.
Work from home	16.1%±3.2Lowest U.S.: 15.1%	20%±2.7Highest U.S.: 15.1%
	Dedham 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	#119 of 282 in MA
School district	Capitol Region Education Council · Windsor School District	Dedham
High school in town	Windsor High School	Dedham High
Students per teacherat that high school	10.2Lowest	10.4Highest
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.