What stands out worked out from the figures below

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

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	Wakefield	Winchester
People
Population	27,793Highest	10,284Lowest
Growth since 20102010 → 2020 census	+8.7% U.S.: +7.4%	—
Median age	42.4±1.7Lowest 9% above U.S.	49.1±6.2Highest 26% 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	20%±2.2Highest U.S.: 22%	15.4%±2.9Lowest 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+	19%±1.9Lowest U.S.: 17.2%	27.4%±5.1Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	59.7%Highest U.S.: 35.7%	27.8%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	4.4%±0.9Highest U.S.: 6.4%	4.2%±1.7Lowest 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	$134,306±$14kHighest 66% above U.S.	$66,519±$12kLowest 18% below U.S.
Home valuemedian, owner-occupied	$723,500±$24kHighest 117% above U.S.	$249,500±$17kLowest 25% below U.S.
Rentmedian gross, monthly	$1,958±$102Highest 39% above U.S.	$1,174±$116Lowest 17% below U.S.
Property taxmedian, yearly	$7,779Highest 149% above U.S.	$4,780Lowest 53% above U.S.
Renters paying 30%+of income on rent	43.7%±7.9Lowest U.S.: 51.1%	48.9%±15.8Highest 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	4.9%Lowest U.S.: 12.5%	12.8%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	70.7%Highest U.S.: 65.2%	65.8%Lowest U.S.: 65.2%
Typical home builtmedian year	1956Highest 24 yrs older than U.S.	1955Lowest 25 yrs older than U.S.
Getting to work
Average commuteone way	33 minHighest 26% above U.S.	26 minLowest about the U.S. average
Work from home	24.6%±3.1Highest U.S.: 15.1%	6.9%±2.7Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#179 of 282 in MA	#97 of 149 in CT
School district	Northeast Metropolitan Regional Vocational Technical · Wakefield	Explorations District · Regional School District 07
High school in town	Northeast Metro Regional Vocational	Northwestern Regional High School
Students per teacherat that high school	10.7Highest	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.