What stands out worked out from the figures below

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

Sutton has the most affordable homes ($523k 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	Winchester	Sutton
People
Population	23,406Highest	9,452Lowest
Growth since 20102010 → 2020 census	+7.5%Highest MA: +7.4%	+4.4%Lowest MA: +7.4%
Median age	42.5±1.9Lowest 6% above MA	44.3±2.5Highest 11% above MA
	Sutton 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%	19.6%±3.3Lowest MA: 19.4%
Age 65+	18%±2Lowest MA: 17.9%	18.8%±3.2Highest MA: 17.9%
	Sutton and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	79.5%Highest MA: 47.3%	52.8%Lowest MA: 47.3%
Enrolled in collegeshare of residents	4.9%±1.3Highest MA: 7.9%	3.9%±1.8Lowest MA: 7.9%
	Winchester and Sutton are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$230,198±$21kHighest 121% above MA	$147,125±$25kLowest 42% above MA
Home valuemedian, owner-occupied	$1,215,200±$39kHighest 116% above MA	$523,100±$47kLowest 7% below MA
Rentmedian gross, monthly	$2,279±$481Highest 29% above MA	$1,190±$401Lowest 32% below MA
Property taxmedian, yearly	$10,000+Highest at least 67% above MA	$6,763Lowest 13% above MA
Renters paying 30%+of income on rent	39.3%±13.3Lowest MA: 51.8%	47.5%±24.4Highest MA: 51.8%
	Sutton and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.7%Lowest MA: 10%	5.8%Highest MA: 10%
Housing
Homeownersof occupied homes	81.7%Lowest MA: 62.5%	89.7%Highest MA: 62.5%
Typical home builtmedian year	1954Lowest 10 yrs older than MA	1981Highest 17 yrs newer than MA
Getting to work
Average commuteone way	31 minHighest 8% above MA	30 minLowest about the MA average
Work from home	33.8%±3Highest MA: 18.6%	22.7%±4.1Lowest MA: 18.6%
Schools
Public school scoresrank in state, math + reading	#11 of 282 in MA	#105 of 282 in MA
School district	Winchester	Sutton
High school in town	Winchester High School	Sutton High School
Students per teacherat that high school	14.8Highest	12.6Lowest
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.