What stands out worked out from the figures below

Pittsfield has the most expensive homes ($295k median).

Windsor has grown the fastest since 2010 (+0.2%).

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	Windsor
People
Population	4,105Highest	3,554Lowest
Growth since 20102010 → 2020 census	-0.8%Lowest U.S.: +7.4%	+0.2%Highest U.S.: +7.4%
Median age	41.5±5.1Lowest 7% above U.S.	44.8±6.5Highest 15% above U.S.
	Windsor and Pittsfield are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	20.8%±6Highest U.S.: 22%	19.5%±5.2Lowest U.S.: 22%
	Pittsfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.7%±4.6Lowest U.S.: 17.2%	29.7%±6.9Highest U.S.: 17.2%
	Windsor and Pittsfield are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	22.7%Lowest U.S.: 35.7%	39.7%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	4.5%±3.1Highest U.S.: 6.4%	0.7%±0.8Lowest U.S.: 6.4%
	Pittsfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$74,318±$14kHighest 8% below U.S.	$52,484±$11kLowest 35% below U.S.
	Pittsfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$294,800±$30kHighest 11% below U.S.	$207,500±$31kLowest 38% below U.S.
Rentmedian gross, monthly	$1,239±$182Highest 12% below U.S.	$1,026±$89Lowest 27% below U.S.
	Pittsfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$5,694Highest 83% above U.S.	$5,209Lowest 67% above U.S.
Renters paying 30%+of income on rent	67.5%±27.3Highest U.S.: 51.1%	31.5%±17Lowest U.S.: 51.1%
	Pittsfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	11.3%Highest U.S.: 12.5%	7.8%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	68.8%Highest U.S.: 65.2%	57.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1980Highest same as U.S.	1945Lowest 35 yrs older than U.S.
Getting to work
Average commuteone way	27 minHighest about the U.S. average	23 minLowest 14% below U.S.
Work from home	11.6%±5Highest U.S.: 15.1%	10.3%±5Lowest U.S.: 15.1%
	Pittsfield and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Schools
Public school scoresrank in state, math + reading	#93 of 120 in NH	#61 of 70 in VT
School district	Pittsfield School District	—
High school in town	Pittsfield High School	—
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.