What stands out worked out from the figures below

Randolph Town has the most affordable homes ($496k median).

Winchester has the most expensive homes ($1215k median).

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	Randolph Town	Winchester
People
Population	34,878Highest	23,406Lowest
Growth since 20102010 → 2020 census	—	+7.5% MA: +7.4%
Median age	41.3±1.8Lowest 3% above MA	42.5±1.9Highest 6% above MA
	Winchester and Randolph Town are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	17.3%±2Lowest MA: 19.4%	27.6%±2.3Highest MA: 19.4%
Age 65+	18.4%±1.9Highest MA: 17.9%	18%±2Lowest MA: 17.9%
	Randolph Town and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	35.5%Lowest MA: 47.3%	79.5%Highest MA: 47.3%
Enrolled in collegeshare of residents	9%±1.8Highest MA: 7.9%	4.9%±1.3Lowest MA: 7.9%
Cost of living
Household incomemedian	$109,573±$6kLowest 5% above MA	$230,198±$21kHighest 121% above MA
Home valuemedian, owner-occupied	$496,400±$21kLowest 12% below MA	$1,215,200±$39kHighest 116% above MA
Rentmedian gross, monthly	$2,103±$98Lowest 19% above MA	$2,279±$481Highest 29% above MA
	Winchester and Randolph Town are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$5,644Lowest 6% below MA	$10,000+Highest at least 67% above MA
Renters paying 30%+of income on rent	62.1%±10.4Highest MA: 51.8%	39.3%±13.3Lowest MA: 51.8%
	Randolph Town and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	8.4%Highest MA: 10%	4.7%Lowest MA: 10%
Housing
Homeownersof occupied homes	71.3%Lowest MA: 62.5%	81.7%Highest MA: 62.5%
Typical home builtmedian year	1966Highest 2 yrs newer than MA	1954Lowest 10 yrs older than MA
Getting to work
Average commuteone way	37 minHighest 27% above MA	31 minLowest 8% above MA
Work from home	15.1%±3.5Lowest MA: 18.6%	33.8%±3Highest MA: 18.6%
Schools
Public school scoresrank in state, math + reading	#260 of 282 in MA	#11 of 282 in MA
School district	Randolph	Winchester
High school in town	Randolph High	Winchester High School
Students per teacherat that high school	14.2Lowest	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.