What stands out worked out from the figures below

Whitman has the most expensive homes ($473k median).

Winchester has the most affordable homes ($250k 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	Whitman	Winchester
People
Population	15,295Highest	10,284Lowest
Growth since 20102010 → 2020 census	+4.4% U.S.: +7.4%	—
Median age	40.4±1.8Lowest 4% above U.S.	49.1±6.2Highest 26% above U.S.
Kids under 18	21.1%±3.5Highest U.S.: 22%	15.4%±2.9Lowest U.S.: 22%
	Whitman and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	15.5%±2.1Lowest U.S.: 17.2%	27.4%±5.1Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	31.3%Highest U.S.: 35.7%	27.8%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.1%±1.2Highest U.S.: 6.4%	4.2%±1.7Lowest U.S.: 6.4%
	Whitman and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$108,933±$14kHighest 35% above U.S.	$66,519±$12kLowest 18% below U.S.
Home valuemedian, owner-occupied	$472,700±$12kHighest 42% above U.S.	$249,500±$17kLowest 25% below U.S.
Rentmedian gross, monthly	$1,771±$151Highest 25% above U.S.	$1,174±$116Lowest 17% below U.S.
Property taxmedian, yearly	$5,824Highest 87% above U.S.	$4,780Lowest 53% above U.S.
Renters paying 30%+of income on rent	61.9%±13.4Highest U.S.: 51.1%	48.9%±15.8Lowest U.S.: 51.1%
	Whitman and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	7.9%Lowest U.S.: 12.5%	12.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	71.4%Highest U.S.: 65.2%	65.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1957Highest 23 yrs older than U.S.	1955Lowest 25 yrs older than U.S.
Getting to work
Average commuteone way	36 minHighest 37% above U.S.	26 minLowest about the U.S. average
Work from home	10.8%±2.4Highest U.S.: 15.1%	6.9%±2.7Lowest U.S.: 15.1%
	Whitman and Winchester 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	#191 of 282 in MA	#97 of 149 in CT
School district	Whitman-Hanson	Explorations District · Regional School District 07
High school in town	None in town	Northwestern Regional High School
Students per teacherat that high school	—	9.7
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.