What stands out worked out from the figures below

Webster has the most affordable homes ($362k median).

Winchester has the most people working from home (33.8%).

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	Webster	Winchester
People
Population	17,748Lowest	23,406Highest
Growth since 20102010 → 2020 census	+6%Lowest MA: +7.4%	+7.5%Highest MA: +7.4%
Median age	39.9±2.9Lowest about the MA average	42.5±1.9Highest 6% above MA
	Winchester and Webster are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	19.6%±2.9Lowest MA: 19.4%	27.6%±2.3Highest MA: 19.4%
Age 65+	19.6%±2.5Highest MA: 17.9%	18%±2Lowest MA: 17.9%
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	25.3%Lowest MA: 47.3%	79.5%Highest MA: 47.3%
Enrolled in collegeshare of residents	5.8%±1.6Highest MA: 7.9%	4.9%±1.3Lowest MA: 7.9%
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$72,895±$6kLowest 30% below MA	$230,198±$21kHighest 121% above MA
Home valuemedian, owner-occupied	$361,500±$12kLowest 36% below MA	$1,215,200±$39kHighest 116% above MA
Rentmedian gross, monthly	$1,228±$81Lowest 30% below MA	$2,279±$481Highest 29% above MA
Property taxmedian, yearly	$3,999Lowest 33% below MA	$10,000+Highest at least 67% above MA
Renters paying 30%+of income on rent	45.7%±6.7Highest MA: 51.8%	39.3%±13.3Lowest MA: 51.8%
	Webster and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	12.7%Highest MA: 10%	4.7%Lowest MA: 10%
Housing
Homeownersof occupied homes	59.8%Lowest MA: 62.5%	81.7%Highest MA: 62.5%
Typical home builtmedian year	1962Highest 2 yrs older than MA	1954Lowest 10 yrs older than MA
Getting to work
Average commuteone way	31 minLowest 5% above MA	31 minHighest 8% above MA
Work from home	8%±2.5Lowest MA: 18.6%	33.8%±3Highest MA: 18.6%
Schools
Public school scoresrank in state, math + reading	#271 of 282 in MA	#11 of 282 in MA
School district	Webster	Winchester
High school in town	Bartlett High School	Winchester High School
Students per teacherat that high school	11.6Lowest	14.8Highest
On TownTapestry
Old photos in History	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.