What stands out worked out from the figures below

Wellesley has the most expensive homes ($1583k median).

Winchester has grown the fastest since 2010 (+7.5%).

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	Wellesley	Winchester
People
Population	30,347Highest	23,406Lowest
Growth since 20102010 → 2020 census	+5.6%Lowest MA: +7.4%	+7.5%Highest MA: +7.4%
Median age	37.1±2.2Lowest 7% below MA	42.5±1.9Highest 6% above MA
Kids under 18	24.1%±2Lowest MA: 19.4%	27.6%±2.3Highest MA: 19.4%
	Winchester and Wellesley are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	15.5%±1.3Lowest MA: 17.9%	18%±2Highest MA: 17.9%
	Winchester and Wellesley are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	89%Highest MA: 47.3%	79.5%Lowest MA: 47.3%
Enrolled in collegeshare of residents	18.3%±0.7Highest MA: 7.9%	4.9%±1.3Lowest MA: 7.9%
Cost of living
Household incomemedian	$250,001Highest 140% above MA	$230,198±$21kLowest 121% above MA
Home valuemedian, owner-occupied	$1,582,700±$49kHighest 182% above MA	$1,215,200±$39kLowest 116% above MA
Rentmedian gross, monthly	$2,886±$360Highest 64% above MA	$2,279±$481Lowest 29% above MA
	Wellesley and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$10,000+ at least 67% above MA	$10,000+ at least 67% above MA
Renters paying 30%+of income on rent	44.1%±8.2Highest MA: 51.8%	39.3%±13.3Lowest MA: 51.8%
	Wellesley and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4%Lowest MA: 10%	4.7%Highest MA: 10%
Housing
Homeownersof occupied homes	84.4%Highest MA: 62.5%	81.7%Lowest MA: 62.5%
Typical home builtmedian year	1955Highest 9 yrs older than MA	1954Lowest 10 yrs older than MA
Getting to work
Average commuteone way	27 minLowest 7% below MA	31 minHighest 8% above MA
Work from home	32%±2.9Lowest MA: 18.6%	33.8%±3Highest MA: 18.6%
	Winchester and Wellesley 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	#6 of 282 in MA	#11 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 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.