What stands out worked out from the figures below

Stoddard has the most affordable homes ($330k 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	Stoddard	Winchester
People
Population	1,072Lowest	23,406Highest
Growth since 20102010 → 2020 census	+11.5%Highest U.S.: +7.4%	+7.5%Lowest U.S.: +7.4%
Median age	53±4Highest 36% above U.S.	42.5±1.9Lowest 9% above U.S.
Kids under 18	17.5%±3.4Lowest U.S.: 22%	27.6%±2.3Highest U.S.: 22%
Age 65+	24.4%±2.5Highest U.S.: 17.2%	18%±2Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	34.1%Lowest U.S.: 35.7%	79.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	3.5%±1.7Lowest U.S.: 6.4%	4.9%±1.3Highest U.S.: 6.4%
	Winchester and Stoddard are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$94,904±$11kLowest 18% above U.S.	$230,198±$21kHighest 185% above U.S.
Home valuemedian, owner-occupied	$330,300±$20kLowest about the U.S. average	$1,215,200±$39kHighest 265% above U.S.
Rentmedian gross, monthly	$895±$751Lowest 37% below U.S.	$2,279±$481Highest 61% above U.S.
Property taxmedian, yearly	$4,316Lowest 38% above U.S.	$10,000+Highest at least 221% above U.S.
Renters paying 30%+of income on rent	52.6%±100Highest U.S.: 51.1%	39.3%±13.3Lowest U.S.: 51.1%
	Stoddard and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.8%Highest U.S.: 12.5%	4.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	93.3%Highest U.S.: 65.2%	81.7%Lowest U.S.: 65.2%
Typical home builtmedian year	1978Highest 2 yrs older than U.S.	1954Lowest 26 yrs older than U.S.
Getting to work
Average commuteone way	34 minHighest 27% above U.S.	31 minLowest 19% above U.S.
Work from home	9.5%±4Lowest U.S.: 15.1%	33.8%±3Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	—	#11 of 282 in MA
School district	Stoddard School District	Winchester
High school in town	None in town	Winchester High School
Students per teacherat that high school	—	14.8
On TownTapestry
Old photos in History	None yet	None yet

U.S. 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.