What stands out worked out from the figures below

Winchester has the most kids (18.9% under 18).

Chester has the most people working from home (14%).

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	Chester
People
Population	4,212Highest	2,992Lowest
Growth since 20102010 → 2020 census	-4.4%Highest U.S.: +7.4%	-4.7%Lowest U.S.: +7.4%
Median age	42.6±4.5Lowest 10% above U.S.	49.7±4.7Highest 28% above U.S.
	Chester and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	18.9%±4.7Highest U.S.: 22%	14.1%±4.7Lowest U.S.: 22%
	Winchester and Chester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	17.9%±3.9Lowest U.S.: 17.2%	29.8%±7.9Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	20.3%Lowest U.S.: 35.7%	33.1%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	2.4%±1.8Lowest U.S.: 6.4%	5.1%±4Highest U.S.: 6.4%
	Chester and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$67,723±$11kHighest 16% below U.S.	$62,125±$8kLowest 23% below U.S.
	Winchester and Chester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$242,900±$20kHighest 27% below U.S.	$232,900±$44kLowest 30% below U.S.
	Winchester and Chester are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly	$1,209±$143Highest 14% below U.S.	$960±$44Lowest 32% below U.S.
Property taxmedian, yearly	$5,314Highest 70% above U.S.	$4,262Lowest 37% above U.S.
Renters paying 30%+of income on rent	45%±17.7Highest U.S.: 51.1%	11.5%±12.3Lowest U.S.: 51.1%
Below poverty line	14.1%Highest U.S.: 12.5%	7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	72.7%Lowest U.S.: 65.2%	86.7%Highest U.S.: 65.2%
Typical home builtmedian year	1977Highest 3 yrs older than U.S.	1972Lowest 8 yrs older than U.S.
Getting to work
Average commuteone way	29 minHighest 9% above U.S.	28 minLowest 5% above U.S.
Work from home	4.3%±2.4Lowest U.S.: 15.1%	14%±6.9Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#120 of 120 in NH	#49 of 70 in VT
School district	Winchester School District	Green Mountain Unified School District #77
High school in town	None in town	Green Mountain Union High School
Students per teacherat that high school	—	8.7
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.