What stands out worked out from the figures below

Winchester has the most expensive homes ($1215k median).

Windham has the most affordable homes ($389k 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	Winchester	Windham
People
Population	23,406Highest	19,188Lowest
Growth since 20102010 → 2020 census	+7.5%Lowest U.S.: +7.4%	+8.4%Highest U.S.: +7.4%
Median age	42.5±1.9Highest 9% above U.S.	41.8±1.8Lowest 7% above U.S.
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	27.6%±2.3Highest U.S.: 22%	19.2%±2.7Lowest U.S.: 22%
Age 65+	18%±2Highest U.S.: 17.2%	15.9%±2.1Lowest U.S.: 17.2%
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	79.5%Highest U.S.: 35.7%	44.2%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.9%±1.3Highest U.S.: 6.4%	3.9%±1.1Lowest U.S.: 6.4%
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$230,198±$21kHighest 185% above U.S.	$107,934±$14kLowest 34% above U.S.
Home valuemedian, owner-occupied	$1,215,200±$39kHighest 265% above U.S.	$388,900±$22kLowest 17% above U.S.
Rentmedian gross, monthly	$2,279±$481Highest 61% above U.S.	$1,232±$332Lowest 13% below U.S.
Property taxmedian, yearly	$10,000+Highest at least 221% above U.S.	$3,938Lowest 26% above U.S.
Renters paying 30%+of income on rent	39.3%±13.3Highest U.S.: 51.1%	32.7%±14.7Lowest U.S.: 51.1%
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.7%Highest U.S.: 12.5%	3.4%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	81.7%Lowest U.S.: 65.2%	84.6%Highest U.S.: 65.2%
Typical home builtmedian year	1954Lowest 26 yrs older than U.S.	1985Highest 5 yrs newer than U.S.
Getting to work
Average commuteone way	31 minHighest 19% above U.S.	26 minLowest about the U.S. average
Work from home	33.8%±3Highest U.S.: 15.1%	19%±4.1Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#11 of 282 in MA	#95 of 133 in ME
School district	Winchester	RSU 14
High school in town	Winchester High School	Windham High School
Students per teacherat that high school	14.8Highest	12.1Lowest
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.