What stands out worked out from the figures below

Dedham has the most expensive homes ($662k median).

Windsor has the most affordable homes ($338k 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	Dedham	Windsor
People
Population	25,237Highest	254Lowest
Growth since 20102010 → 2020 census	+2.6% U.S.: +7.4%	—
Median age	44.6±1.6Highest 15% above U.S.	40.2±18.8Lowest 3% 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	18.6%±1.9Lowest U.S.: 22%	25.2%±14.7Highest 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+	21.9%±2Highest U.S.: 17.2%	15.7%±8Lowest 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+	55%Highest U.S.: 35.7%	12.6%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.6%±1Highest U.S.: 6.4%	3.9%±4.2Lowest U.S.: 6.4%
	Dedham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$128,955±$10kHighest 60% above U.S.	$103,750±$40kLowest 29% above U.S.
	Dedham and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$661,800±$16kHighest 99% above U.S.	$337,500±$40kLowest about the U.S. average
Rentmedian gross, monthly	$2,042±$182 45% above U.S.	—
Property taxmedian, yearly	$7,918Highest 154% above U.S.	$3,381Lowest 8% above U.S.
Renters paying 30%+of income on rent	56.4%±10Lowest U.S.: 51.1%	66.7%±100Highest U.S.: 51.1%
	Windsor and Dedham are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	5.6%Lowest U.S.: 12.5%	10.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	73.4%Lowest U.S.: 65.2%	96.5%Highest U.S.: 65.2%
Typical home builtmedian year	1956Lowest 24 yrs older than U.S.	1983Highest 3 yrs newer than U.S.
Getting to work
Average commuteone way	29 minLowest 11% above U.S.	32 minHighest 22% above U.S.
Work from home	20%±2.7Highest U.S.: 15.1%	15%±16.5Lowest 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	#119 of 282 in MA	—
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.