What stands out worked out from the figures below

Pittsfield has the most affordable homes ($257k median).

Windham has grown the fastest since 2010 (+8.4%).

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	Pittsfield	Windham
People
Population	43,457Highest	19,188Lowest
Growth since 20102010 → 2020 census	-1.8%Lowest U.S.: +7.4%	+8.4%Highest U.S.: +7.4%
Median age	42.4±2Highest 9% above U.S.	41.8±1.8Lowest 7% above U.S.
	Pittsfield and Windham are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	17.6%±1.4Lowest U.S.: 22%	19.2%±2.7Highest U.S.: 22%
	Windham and Pittsfield are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	19.4%±1.5Highest U.S.: 17.2%	15.9%±2.1Lowest U.S.: 17.2%
	Pittsfield and Windham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	34.2%Lowest U.S.: 35.7%	44.2%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	6.2%±1.1Highest U.S.: 6.4%	3.9%±1.1Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$70,582±$5kLowest 13% below U.S.	$107,934±$14kHighest 34% above U.S.
Home valuemedian, owner-occupied	$256,900±$8kLowest 23% below U.S.	$388,900±$22kHighest 17% above U.S.
Rentmedian gross, monthly	$1,134±$61Lowest 20% below U.S.	$1,232±$332Highest 13% below U.S.
	Windham and Pittsfield are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$4,148Highest 33% above U.S.	$3,938Lowest 26% above U.S.
Renters paying 30%+of income on rent	52.8%±5.7Highest U.S.: 51.1%	32.7%±14.7Lowest U.S.: 51.1%
	Pittsfield and Windham are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	14.9%Highest U.S.: 12.5%	3.4%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	62.8%Lowest U.S.: 65.2%	84.6%Highest U.S.: 65.2%
Typical home builtmedian year	1950Lowest 30 yrs older than U.S.	1985Highest 5 yrs newer than U.S.
Getting to work
Average commuteone way	19 minLowest 30% below U.S.	26 minHighest about the U.S. average
Work from home	10.2%±2.2Lowest U.S.: 15.1%	19%±4.1Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#251 of 282 in MA	#95 of 133 in ME
School district	Pittsfield	RSU 14
High school in town	Taconic High	Windham High School
Students per teacherat that high school	9.3Lowest	12.1Highest
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.