What stands out worked out from the figures below

Winchester has the most kids (27.6% under 18).

Dover has the most homeowners (97.9%).

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	Dover
People
Population	23,406Highest	2,308Lowest
Growth since 20102010 → 2020 census	+7.5%Lowest MA: +7.4%	+8.3%Highest MA: +7.4%
Median age	42.5±1.9Lowest 6% above MA	47.5±4Highest 19% above MA
	Dover and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	27.6%±2.3Highest MA: 19.4%	20.9%±4.8Lowest MA: 19.4%
	Winchester and Dover are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18%±2Highest MA: 17.9%	15.5%±3.5Lowest MA: 17.9%
	Winchester and Dover are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	79.5%Lowest MA: 47.3%	83.4%Highest MA: 47.3%
Enrolled in collegeshare of residents	4.9%±1.3Lowest MA: 7.9%	9.4%±4.8Highest MA: 7.9%
	Dover and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$230,198±$21kLowest 121% above MA	$250,001Highest 140% above MA
Home valuemedian, owner-occupied	$1,215,200±$39kLowest 116% above MA	$1,308,300±$149kHighest 133% above MA
	Dover and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly	$2,279±$481 29% above MA	—
Property taxmedian, yearly	$10,000+ at least 67% above MA	$10,000+ at least 67% above MA
Renters paying 30%+of income on rent	39.3%±13.3Lowest MA: 51.8%	100%±100Highest MA: 51.8%
	Dover 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 MA: 10%	3.3%Lowest MA: 10%
Housing
Homeownersof occupied homes	81.7%Lowest MA: 62.5%	97.9%Highest MA: 62.5%
Typical home builtmedian year	1954Lowest 10 yrs older than MA	1967Highest 3 yrs newer than MA
Getting to work
Average commuteone way	31 minLowest 8% above MA	37 minHighest 26% above MA
Work from home	33.8%±3Lowest MA: 18.6%	37.4%±8.8Highest MA: 18.6%
	Dover and Winchester 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	#11 of 282 in MA	#1 of 282 in MA
School district	Winchester	—
High school in town	Winchester High School	—
Students per teacherat that high school	14.8	—
On TownTapestry
Old photos in Our Story	None yet	None yet

MA 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.