What stands out worked out from the figures below

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

Windsor has the most affordable homes ($170k 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	2,060Lowest
Growth since 20102010 → 2020 census	+2.6%Lowest U.S.: +7.4%	+3.5%Highest U.S.: +7.4%
Median age	44.6±1.6 15% above U.S.	44.6±12.3 15% above U.S.
Kids under 18	18.6%±1.9Lowest U.S.: 22%	21.1%±8.8Highest 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%±2Lowest U.S.: 17.2%	29.2%±8Highest U.S.: 17.2%
	Windsor and Dedham 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%	40%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.6%±1Highest U.S.: 6.4%	1.2%±1.4Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$128,955±$10kHighest 60% above U.S.	$51,197±$4kLowest 37% below U.S.
Home valuemedian, owner-occupied	$661,800±$16kHighest 99% above U.S.	$170,300±$22kLowest 49% below U.S.
Rentmedian gross, monthly	$2,042±$182Highest 45% above U.S.	$1,002±$107Lowest 29% below U.S.
Property taxmedian, yearly	$7,918Highest 154% above U.S.	$4,878Lowest 56% above U.S.
Renters paying 30%+of income on rent	56.4%±10Highest U.S.: 51.1%	31.4%±20Lowest 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	5.6%Lowest U.S.: 12.5%	7.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	73.4%Highest U.S.: 65.2%	51.6%Lowest U.S.: 65.2%
Typical home builtmedian year	1956Highest 24 yrs older than U.S.	1938Lowest 42 yrs older than U.S.
Getting to work
Average commuteone way	29 minHighest 11% above U.S.	22 minLowest 16% below U.S.
Work from home	20%±2.7Highest U.S.: 15.1%	6.6%±4.7Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#119 of 282 in MA	#61 of 70 in VT
School district	Dedham	—
High school in town	Dedham High	—
Students per teacherat that high school	10.4	—
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.