What stands out worked out from the figures below

Windsor has the most people working from home (21.2%).

Montgomery has grown the fastest since 2010 (-2.3%).

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	Montgomery
People
Population	1,065Highest	796Lowest
Growth since 20102010 → 2020 census	-7.6%Lowest MA: +7.4%	-2.3%Highest MA: +7.4%
Median age	44.8±6.4Lowest 12% above MA	49.7±5.8Highest 24% above MA
	Montgomery 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 MA: 19.4%	22%±5.8Highest MA: 19.4%
	Montgomery 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 MA: 17.9%	24.9%±7Highest MA: 17.9%
	Montgomery 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%Highest MA: 47.3%	38.1%Lowest MA: 47.3%
Enrolled in collegeshare of residents	2.7%±1.7Lowest MA: 7.9%	4.3%±1.6Highest MA: 7.9%
	Montgomery 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±$10kLowest 11% above MA	$123,000±$19kHighest 18% above MA
	Montgomery and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied	$389,700±$32kHighest 31% below MA	$357,500±$29kLowest 36% below MA
	Windsor and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$3,867Lowest 35% below MA	$4,283Highest 29% below MA
Renters paying 30%+of income on rent	0%±100Lowest MA: 51.8%	50%±100Highest MA: 51.8%
	Montgomery and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	3.8%Highest MA: 10%	1.5%Lowest MA: 10%
Housing
Homeownersof occupied homes	96.2%Lowest MA: 62.5%	96.3%Highest MA: 62.5%
Typical home builtmedian year	1970Lowest 6 yrs newer than MA	1978Highest 14 yrs newer than MA
Getting to work
Average commuteone way	37 minHighest 27% above MA	36 minLowest 23% above MA
Work from home	21.2%±5.8Highest MA: 18.6%	9.4%±6Lowest MA: 18.6%
	Windsor and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
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.