What stands out worked out from the figures below

Winchester has the most affordable homes ($250k median).

Whitman has the most expensive homes ($473k 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	Whitman
People
Population	10,284Lowest	15,295Highest
Growth since 20102010 → 2020 census	—	+4.4% U.S.: +7.4%
Median age	49.1±6.2Highest 26% above U.S.	40.4±1.8Lowest 4% above U.S.
Kids under 18	15.4%±2.9Lowest U.S.: 22%	21.1%±3.5Highest 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+	27.4%±5.1Highest U.S.: 17.2%	15.5%±2.1Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	27.8%Lowest U.S.: 35.7%	31.3%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	4.2%±1.7Lowest U.S.: 6.4%	5.1%±1.2Highest 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	$66,519±$12kLowest 18% below U.S.	$108,933±$14kHighest 35% above U.S.
Home valuemedian, owner-occupied	$249,500±$17kLowest 25% below U.S.	$472,700±$12kHighest 42% above U.S.
Rentmedian gross, monthly	$1,174±$116Lowest 17% below U.S.	$1,771±$151Highest 25% above U.S.
Property taxmedian, yearly	$4,780Lowest 53% above U.S.	$5,824Highest 87% above U.S.
Renters paying 30%+of income on rent	48.9%±15.8Lowest U.S.: 51.1%	61.9%±13.4Highest 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	12.8%Highest U.S.: 12.5%	7.9%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	65.8%Lowest U.S.: 65.2%	71.4%Highest U.S.: 65.2%
Typical home builtmedian year	1955Lowest 25 yrs older than U.S.	1957Highest 23 yrs older than U.S.
Getting to work
Average commuteone way	26 minLowest about the U.S. average	36 minHighest 37% above U.S.
Work from home	6.9%±2.7Lowest U.S.: 15.1%	10.8%±2.4Highest 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	#97 of 149 in CT	#191 of 282 in MA
School district	Explorations District · Regional School District 07	Whitman-Hanson
High school in town	Northwestern Regional High School	None in town
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.