What stands out worked out from the figures below

Milton has the most affordable homes ($933k 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	Milton	Winchester
People
Population	28,587Highest	23,406Lowest
Growth since 20102010 → 2020 census	+6%Lowest MA: +7.4%	+7.5%Highest MA: +7.4%
Median age	41.1±1.8Lowest about the MA average	42.5±1.9Highest 6% above MA
	Winchester and Milton are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	25.3%±2.2Lowest MA: 19.4%	27.6%±2.3Highest MA: 19.4%
	Winchester and Milton are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	16.1%±1.8Lowest MA: 17.9%	18%±2Highest MA: 17.9%
	Winchester and Milton are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	71.9%Lowest MA: 47.3%	79.5%Highest MA: 47.3%
Enrolled in collegeshare of residents	9.7%±1.1Highest MA: 7.9%	4.9%±1.3Lowest MA: 7.9%
Cost of living
Household incomemedian	$188,529±$15kLowest 81% above MA	$230,198±$21kHighest 121% above MA
Home valuemedian, owner-occupied	$933,200±$31kLowest 66% above MA	$1,215,200±$39kHighest 116% above MA
Rentmedian gross, monthly	$1,474±$281Lowest 16% below MA	$2,279±$481Highest 29% above MA
Property taxmedian, yearly	$9,677Lowest 61% above MA	$10,000+Highest at least 67% above MA
Renters paying 30%+of income on rent	45.7%±20.9Highest MA: 51.8%	39.3%±13.3Lowest MA: 51.8%
	Milton and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.7% MA: 10%	4.7% MA: 10%
Housing
Homeownersof occupied homes	85.2%Highest MA: 62.5%	81.7%Lowest MA: 62.5%
Typical home builtmedian year	1945Lowest 19 yrs older than MA	1954Highest 10 yrs older than MA
Getting to work
Average commuteone way	31 minLowest 8% above MA	31 minHighest 8% above MA
Work from home	29.7%±2.9Lowest MA: 18.6%	33.8%±3Highest MA: 18.6%
	Winchester and Milton 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	#55 of 282 in MA	#11 of 282 in MA
School district	Milton	Winchester
High school in town	Milton High	Winchester High School
Students per teacherat that high school	12.4Lowest	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.