What stands out worked out from the figures below

Winchester has the most expensive homes ($1215k median).

Douglas has the most affordable homes ($471k 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	Douglas
People
Population	23,406Highest	9,207Lowest
Growth since 20102010 → 2020 census	+7.5%Highest MA: +7.4%	+6%Lowest MA: +7.4%
Median age	42.5±1.9Lowest 6% above MA	44±2.6Highest 10% above MA
	Douglas and Winchester 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%	21.2%±3.8Lowest MA: 19.4%
Age 65+	18%±2Highest MA: 17.9%	15.4%±3.1Lowest MA: 17.9%
	Winchester and Douglas 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%	41.7%Lowest MA: 47.3%
Enrolled in collegeshare of residents	4.9%±1.3Lowest MA: 7.9%	5.4%±2.3Highest MA: 7.9%
	Douglas and Winchester 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	$152,267±$10kLowest 46% above MA
Home valuemedian, owner-occupied	$1,215,200±$39kHighest 116% above MA	$470,600±$29kLowest 16% below MA
Rentmedian gross, monthly	$2,279±$481Highest 29% above MA	$1,503±$697Lowest 15% below MA
	Winchester and Douglas 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	$6,338Lowest 6% above MA
Renters paying 30%+of income on rent	39.3%±13.3Highest MA: 51.8%	33.9%±17.4Lowest MA: 51.8%
	Winchester and Douglas 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%	4.8%Highest MA: 10%
Housing
Homeownersof occupied homes	81.7%Lowest MA: 62.5%	83.8%Highest MA: 62.5%
Typical home builtmedian year	1954Lowest 10 yrs older than MA	1986Highest 22 yrs newer than MA
Getting to work
Average commuteone way	31 minLowest 8% above MA	34 minHighest 16% above MA
Work from home	33.8%±3Highest MA: 18.6%	20.9%±4.9Lowest MA: 18.6%
Schools
Public school scoresrank in state, math + reading	#11 of 282 in MA	#177 of 282 in MA
School district	Winchester	Douglas
High school in town	Winchester High School	Douglas High School
Students per teacherat that high school	14.8Highest	7.2Lowest
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.