What stands out worked out from the figures below

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

Wakefield has the most people working from home (24.6%).

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	Wakefield
People
Population	10,284Lowest	27,793Highest
Growth since 20102010 → 2020 census	—	+8.7% U.S.: +7.4%
Median age	49.1±6.2Highest 26% above U.S.	42.4±1.7Lowest 9% above U.S.
	Winchester and Wakefield are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	15.4%±2.9Lowest U.S.: 22%	20%±2.2Highest U.S.: 22%
	Wakefield 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%	19%±1.9Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	27.8%Lowest U.S.: 35.7%	59.7%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	4.2%±1.7Lowest U.S.: 6.4%	4.4%±0.9Highest U.S.: 6.4%
	Wakefield 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.	$134,306±$14kHighest 66% above U.S.
Home valuemedian, owner-occupied	$249,500±$17kLowest 25% below U.S.	$723,500±$24kHighest 117% above U.S.
Rentmedian gross, monthly	$1,174±$116Lowest 17% below U.S.	$1,958±$102Highest 39% above U.S.
Property taxmedian, yearly	$4,780Lowest 53% above U.S.	$7,779Highest 149% above U.S.
Renters paying 30%+of income on rent	48.9%±15.8Highest U.S.: 51.1%	43.7%±7.9Lowest U.S.: 51.1%
	Winchester and Wakefield 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%	4.9%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	65.8%Lowest U.S.: 65.2%	70.7%Highest U.S.: 65.2%
Typical home builtmedian year	1955Lowest 25 yrs older than U.S.	1956Highest 24 yrs older than U.S.
Getting to work
Average commuteone way	26 minLowest about the U.S. average	33 minHighest 26% above U.S.
Work from home	6.9%±2.7Lowest U.S.: 15.1%	24.6%±3.1Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#97 of 149 in CT	#179 of 282 in MA
School district	Explorations District · Regional School District 07	Northeast Metropolitan Regional Vocational Technical · Wakefield
High school in town	Northwestern Regional High School	Northeast Metro Regional Vocational
Students per teacherat that high school	9.7Lowest	10.7Highest
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.