What stands out worked out from the figures below

Windsor has the most affordable homes ($390k median).

Dorset has grown the fastest since 2010 (+5%).

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	Dorset
People
Population	1,065Lowest	2,092Highest
Growth since 20102010 → 2020 census	-7.6%Lowest U.S.: +7.4%	+5%Highest U.S.: +7.4%
Median age	44.8±6.4Lowest 15% above U.S.	45.9±7.5Highest 18% above U.S.
	Dorset and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	15.8%±5.1Lowest U.S.: 22%	24%±5.5Highest U.S.: 22%
	Dorset and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.6%±4.9Lowest U.S.: 17.2%	21.9%±4.5Highest U.S.: 17.2%
	Dorset and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	41.5%Lowest U.S.: 35.7%	72.1%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	2.7%±1.7Lowest U.S.: 6.4%	2.8%±2.1Highest U.S.: 6.4%
	Dorset and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$115,563±$10kHighest 43% above U.S.	$111,250±$40kLowest 38% above U.S.
	Windsor and Dorset are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$389,700±$32kLowest 17% above U.S.	$569,200±$57kHighest 71% above U.S.
Rentmedian gross, monthly	—	$1,420±$296 about the U.S. average
Property taxmedian, yearly	$3,867Lowest 24% above U.S.	$7,489Highest 140% above U.S.
Renters paying 30%+of income on rent	0%±100Lowest U.S.: 51.1%	74.4%±22.5Highest U.S.: 51.1%
	Dorset and Windsor 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%	11.2%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	96.2%Highest U.S.: 65.2%	90.7%Lowest U.S.: 65.2%
Typical home builtmedian year	1970Lowest 10 yrs older than U.S.	1972Highest 8 yrs older than U.S.
Getting to work
Average commuteone way	37 minHighest 41% above U.S.	22 minLowest 18% below U.S.
Work from home	21.2%±5.8Lowest U.S.: 15.1%	29.3%±7.5Highest U.S.: 15.1%
	Dorset and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Schools
School district	—	Taconic and Green Regional School District #63
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.