What stands out worked out from the figures below

Windsor has the most kids (25.2% under 18).

Middlebury has the shortest commute (16 min average).

Middlebury is a college town. 32.6% of residents are enrolled in college, which pulls its median age, poverty rate and renter figures away from what a year-round family would see.

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	Middlebury
People
Population	254Lowest	9,175Highest
Growth since 20102010 → 2020 census	—	+7.7% U.S.: +7.4%
Median age	40.2±18.8Highest 3% above U.S.	31.8±3.7Lowest 18% below U.S.
	Windsor and Middlebury are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	25.2%±14.7Highest U.S.: 22%	11.6%±1.9Lowest U.S.: 22%
	Windsor and Middlebury are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	15.7%±8Lowest U.S.: 17.2%	20.7%±2.6Highest U.S.: 17.2%
	Middlebury and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	12.6%Lowest U.S.: 35.7%	55.4%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	3.9%±4.2Lowest U.S.: 6.4%	32.6%±1.1Highest U.S.: 6.4%
Cost of living
Household incomemedian	$103,750±$40kHighest 29% above U.S.	$86,169±$16kLowest 7% above U.S.
	Windsor and Middlebury are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$337,500±$40kLowest about the U.S. average	$409,700±$30kHighest 23% above U.S.
Rentmedian gross, monthly	—	$1,156±$113 18% below U.S.
Property taxmedian, yearly	$3,381Lowest 8% above U.S.	$6,868Highest 120% above U.S.
Renters paying 30%+of income on rent	66.7%±100Highest U.S.: 51.1%	50.9%±14.4Lowest U.S.: 51.1%
	Windsor and Middlebury are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	10.8%Highest U.S.: 12.5%	10.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	96.5%Highest U.S.: 65.2%	65.1%Lowest U.S.: 65.2%
Typical home builtmedian year	1983Highest 3 yrs newer than U.S.	1976Lowest 4 yrs older than U.S.
Getting to work
Average commuteone way	32 minHighest 22% above U.S.	16 minLowest 41% below U.S.
Work from home	15%±16.5Lowest U.S.: 15.1%	18.8%±4.1Highest U.S.: 15.1%
	Middlebury and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Schools
Public school scoresrank in state, math + reading	—	#17 of 70 in VT
School district	—	Patricia Hannaford Career Center · Addison Central Unified Union School District #55
High school in town	—	Middlebury Union High School
Students per teacherat that high school	—	12.6
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.