What stands out worked out from the figures below

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

Windham has grown the fastest since 2010 (+16.4%).

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	16,038Lowest
Growth since 20102010 → 2020 census	+7.5%Lowest U.S.: +7.4%	+16.4%Highest U.S.: +7.4%
Median age	42.5±1.9Highest 9% above U.S.	41.1±2.9Lowest 6% 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%	27.4%±3.3Lowest U.S.: 22%
	Winchester and Windham are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18%±2Highest U.S.: 17.2%	15.5%±2.6Lowest 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%	62.7%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.9%±1.3Highest U.S.: 6.4%	3.8%±1.8Lowest 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.	$189,583±$19kLowest 135% above U.S.
Home valuemedian, owner-occupied	$1,215,200±$39kHighest 265% above U.S.	$723,300±$50kLowest 117% above U.S.
Rentmedian gross, monthly	$2,279±$481Lowest 61% above U.S.	$3,218±$350Highest 128% above U.S.
Property taxmedian, yearly	$10,000+ at least 221% above U.S.	$10,000+ at least 221% above U.S.
Renters paying 30%+of income on rent	39.3%±13.3Lowest U.S.: 51.1%	52.2%±50.9Highest U.S.: 51.1%
	Windham and Winchester 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%	2%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	81.7%Lowest U.S.: 65.2%	93.9%Highest U.S.: 65.2%
Typical home builtmedian year	1954Lowest 26 yrs older than U.S.	1996Highest 16 yrs newer than U.S.
Getting to work
Average commuteone way	31 minHighest 19% above U.S.	31 minLowest 17% above U.S.
Work from home	33.8%±3Highest U.S.: 15.1%	21.9%±4.4Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#11 of 282 in MA	#13 of 120 in NH
School district	Winchester	Windham School District
High school in town	Winchester High School	Windham High School
Students per teacherat that high school	14.8Highest	12.8Lowest
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.