What stands out worked out from the figures below

Dudley has the most expensive homes ($393k 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	Dudley	Winchester
People
Population	11,929Highest	10,284Lowest
Growth since 20102010 → 2020 census	+4.7% U.S.: +7.4%	—
Median age	40.2±2.4Lowest 3% above U.S.	49.1±6.2Highest 26% above U.S.
Kids under 18	20.6%±3.3Highest U.S.: 22%	15.4%±2.9Lowest U.S.: 22%
	Dudley and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	16.9%±3Lowest U.S.: 17.2%	27.4%±5.1Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	24.1%Lowest U.S.: 35.7%	27.8%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	13.1%±2Highest U.S.: 6.4%	4.2%±1.7Lowest U.S.: 6.4%
Cost of living
Household incomemedian	$84,604±$12kHighest 5% above U.S.	$66,519±$12kLowest 18% below U.S.
	Dudley and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$392,600±$19kHighest 18% above U.S.	$249,500±$17kLowest 25% below U.S.
Rentmedian gross, monthly	$1,217±$182Highest 14% below U.S.	$1,174±$116Lowest 17% below U.S.
	Dudley and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$3,691Lowest 18% above U.S.	$4,780Highest 53% above U.S.
Renters paying 30%+of income on rent	47.4%±4.1Lowest U.S.: 51.1%	48.9%±15.8Highest U.S.: 51.1%
	Winchester and Dudley are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	6.4%Lowest U.S.: 12.5%	12.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	73.1%Highest U.S.: 65.2%	65.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1967Highest 13 yrs older than U.S.	1955Lowest 25 yrs older than U.S.
Getting to work
Average commuteone way	27 minHighest 4% above U.S.	26 minLowest about the U.S. average
Work from home	9.1%±2.5Highest U.S.: 15.1%	6.9%±2.7Lowest U.S.: 15.1%
	Dudley 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	#142 of 282 in MA	#97 of 149 in CT
School district	Dudley-Charlton Reg	Explorations District · Regional School District 07
High school in town	Shepherd Hill Regional High	Northwestern Regional High School
Students per teacherat that high school	14.3Highest	9.7Lowest
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.