What stands out worked out from the figures below

Winchester has the highest household income ($230k).

Wakefield has the most affordable homes ($724k 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	Wakefield
People
Population	23,406Lowest	27,793Highest
Growth since 20102010 → 2020 census	+7.5%Lowest MA: +7.4%	+8.7%Highest MA: +7.4%
Median age	42.5±1.9Highest 6% above MA	42.4±1.7Lowest 6% above MA
	Winchester and Wakefield are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	27.6%±2.3Highest MA: 19.4%	20%±2.2Lowest MA: 19.4%
Age 65+	18%±2Lowest MA: 17.9%	19%±1.9Highest MA: 17.9%
	Wakefield and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	79.5%Highest MA: 47.3%	59.7%Lowest MA: 47.3%
Enrolled in collegeshare of residents	4.9%±1.3Highest MA: 7.9%	4.4%±0.9Lowest MA: 7.9%
	Winchester and Wakefield are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$230,198±$21kHighest 121% above MA	$134,306±$14kLowest 29% above MA
Home valuemedian, owner-occupied	$1,215,200±$39kHighest 116% above MA	$723,500±$24kLowest 29% above MA
Rentmedian gross, monthly	$2,279±$481Highest 29% above MA	$1,958±$102Lowest 11% above MA
	Winchester and Wakefield are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$10,000+Highest at least 67% above MA	$7,779Lowest 30% above MA
Renters paying 30%+of income on rent	39.3%±13.3Lowest MA: 51.8%	43.7%±7.9Highest MA: 51.8%
	Wakefield and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.7%Lowest MA: 10%	4.9%Highest MA: 10%
Housing
Homeownersof occupied homes	81.7%Highest MA: 62.5%	70.7%Lowest MA: 62.5%
Typical home builtmedian year	1954Lowest 10 yrs older than MA	1956Highest 8 yrs older than MA
Getting to work
Average commuteone way	31 minLowest 8% above MA	33 minHighest 14% above MA
Work from home	33.8%±3Highest MA: 18.6%	24.6%±3.1Lowest MA: 18.6%
Schools
Public school scoresrank in state, math + reading	#11 of 282 in MA	#179 of 282 in MA
School district	Winchester	Northeast Metropolitan Regional Vocational Technical · Wakefield
High school in town	Winchester High School	Northeast Metro Regional Vocational
Students per teacherat that high school	14.8Highest	10.7Lowest
On TownTapestry
Old photos in History	None yet	None yet

MA 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.