What stands out worked out from the figures below

Middlesex has the most people working from home (28.4%).

Winchester has the most affordable homes ($243k 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	Middlesex	Winchester
People
Population	1,943Lowest	4,212Highest
Growth since 20102010 → 2020 census	+2.8%Highest U.S.: +7.4%	-4.4%Lowest U.S.: +7.4%
Median age	44.4±3.9Highest 14% above U.S.	42.6±4.5Lowest 10% above U.S.
	Middlesex and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	21.3%±3.1Highest U.S.: 22%	18.9%±4.7Lowest U.S.: 22%
	Middlesex and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	20.6%±3.7Highest U.S.: 17.2%	17.9%±3.9Lowest U.S.: 17.2%
	Middlesex and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	54.7%Highest U.S.: 35.7%	20.3%Lowest U.S.: 35.7%
Enrolled in collegeshare of residents	5.2%±2.6Highest U.S.: 6.4%	2.4%±1.8Lowest U.S.: 6.4%
	Middlesex and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$109,632±$13kHighest 36% above U.S.	$67,723±$11kLowest 16% below U.S.
Home valuemedian, owner-occupied	$376,300±$40kHighest 13% above U.S.	$242,900±$20kLowest 27% below U.S.
Rentmedian gross, monthly	$1,333±$359Highest 6% below U.S.	$1,209±$143Lowest 14% below U.S.
	Middlesex and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$6,483Highest 108% above U.S.	$5,314Lowest 70% above U.S.
Renters paying 30%+of income on rent	0%±100Lowest U.S.: 51.1%	45%±17.7Highest U.S.: 51.1%
	Winchester and Middlesex are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	3.8%Lowest U.S.: 12.5%	14.1%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	96.7%Highest U.S.: 65.2%	72.7%Lowest U.S.: 65.2%
Typical home builtmedian year	1986Highest 6 yrs newer than U.S.	1977Lowest 3 yrs older than U.S.
Getting to work
Average commuteone way	27 minLowest 4% above U.S.	29 minHighest 9% above U.S.
Work from home	28.4%±10.7Highest U.S.: 15.1%	4.3%±2.4Lowest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	—	#120 of 120 in NH
School district	Washington Central Unified Union School District #92	Winchester School District
High school in town	None in town	None in town
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.