What stands out worked out from the figures below

Dedham has the most people working from home (20%).

Windham has the most affordable homes ($210k 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	Windham
People
Population	25,237Highest	23,961Lowest
Growth since 20102010 → 2020 census	+2.6% U.S.: +7.4%	—
Median age	44.6±1.6Highest 15% above U.S.	33.7±1.9Lowest 13% below U.S.
Kids under 18	18.6%±1.9Lowest U.S.: 22%	20.1%±2.4Highest U.S.: 22%
	Windham 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%	14.3%±1.9Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	55%Highest U.S.: 35.7%	22.7%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.6%±1Lowest U.S.: 6.4%	15.2%±1.8Highest U.S.: 6.4%
Cost of living
Household incomemedian	$128,955±$10kHighest 60% above U.S.	$55,736±$5kLowest 31% below U.S.
Home valuemedian, owner-occupied	$661,800±$16kHighest 99% above U.S.	$209,800±$9kLowest 37% below U.S.
Rentmedian gross, monthly	$2,042±$182Highest 45% above U.S.	$1,107±$69Lowest 22% below U.S.
Property taxmedian, yearly	$7,918Highest 154% above U.S.	$4,633Lowest 49% above U.S.
Renters paying 30%+of income on rent	56.4%±10Lowest U.S.: 51.1%	57.1%±8.1Highest U.S.: 51.1%
	Windham 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%	20.7%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	73.4%Highest U.S.: 65.2%	47.4%Lowest U.S.: 65.2%
Typical home builtmedian year	1956 24 yrs older than U.S.	1956 24 yrs older than U.S.
Getting to work
Average commuteone way	29 minHighest 11% above U.S.	24 minLowest 8% below U.S.
Work from home	20%±2.7Highest U.S.: 15.1%	6.1%±1.7Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#119 of 282 in MA	#143 of 149 in CT
School district	Dedham	Connecticut Technical Education and Career System · Eastern Connecticut Regional Educational Service Center (EAS
High school in town	Dedham High	Windham High School
Students per teacherat that high school	10.4Highest	9.8Lowest
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.