What stands out worked out from the figures below

Windsor has the most affordable homes ($170k median).

Ashby has the most people working from home (17.8%).

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	Windsor	Ashby
People
Population	2,060Lowest	3,211Highest
Growth since 20102010 → 2020 census	+3.5%Lowest U.S.: +7.4%	+3.9%Highest U.S.: +7.4%
Median age	44.6±12.3Lowest 15% above U.S.	50.5±3Highest 30% above U.S.
	Ashby and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	21.1%±8.8Highest U.S.: 22%	17%±3.5Lowest U.S.: 22%
	Windsor and Ashby are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	29.2%±8Highest U.S.: 17.2%	21.5%±4.3Lowest U.S.: 17.2%
	Windsor and Ashby are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	40%Lowest U.S.: 35.7%	43.7%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	1.2%±1.4Lowest U.S.: 6.4%	3%±1.2Highest U.S.: 6.4%
	Ashby and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$51,197±$4kLowest 37% below U.S.	$115,598±$9kHighest 43% above U.S.
Home valuemedian, owner-occupied	$170,300±$22kLowest 49% below U.S.	$390,500±$30kHighest 17% above U.S.
Rentmedian gross, monthly	$1,002±$107Lowest 29% below U.S.	$1,200±$484Highest 15% below U.S.
	Ashby and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$4,878Lowest 56% above U.S.	$6,034Highest 93% above U.S.
Renters paying 30%+of income on rent	31.4%±20Lowest U.S.: 51.1%	36.4%±53.5Highest U.S.: 51.1%
	Ashby and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	7.8%Highest U.S.: 12.5%	2.6%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	51.6%Lowest U.S.: 65.2%	95.5%Highest U.S.: 65.2%
Typical home builtmedian year	1938Lowest 42 yrs older than U.S.	1970Highest 10 yrs older than U.S.
Getting to work
Average commuteone way	22 minLowest 16% below U.S.	33 minHighest 25% above U.S.
Work from home	6.6%±4.7Lowest U.S.: 15.1%	17.8%±5.8Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#61 of 70 in VT	#200 of 282 in MA
School district	—	North Middlesex
High school 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.