What stands out worked out from the figures below

Windsor has the most kids (15.8% under 18).

Middlefield has the oldest population (median age 56.9).

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	Middlefield
People
Population	1,065Highest	352Lowest
Growth since 20102010 → 2020 census	-7.6%Highest MA: +7.4%	-26.1%Lowest MA: +7.4%
Median age	44.8±6.4Lowest 12% above MA	56.9±3.7Highest 42% above MA
Kids under 18	15.8%±5.1Highest MA: 19.4%	4.5%±9.5Lowest MA: 19.4%
	Windsor and Middlefield 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%	28.7%±8.5Highest MA: 17.9%
	Middlefield 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%	31.8%Lowest MA: 47.3%
Enrolled in collegeshare of residents	2.7%±1.7Lowest MA: 7.9%	2.8%±4.8Highest MA: 7.9%
	Middlefield 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 11% above MA	$103,750±$23kLowest about the MA average
	Windsor and Middlefield 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	$332,800±$48kLowest 41% below MA
	Windsor and Middlefield are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly	—	$2,625±$1k 49% above MA
Property taxmedian, yearly	$3,867Lowest 35% below MA	$4,926Highest 18% below MA
Renters paying 30%+of income on rent	0%±100Lowest MA: 51.8%	100%±100Highest MA: 51.8%
	Middlefield 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 MA: 10%	12.2%Highest MA: 10%
Housing
Homeownersof occupied homes	96.2%Highest MA: 62.5%	94.1%Lowest MA: 62.5%
Typical home builtmedian year	1970Lowest 6 yrs newer than MA	1971Highest 7 yrs newer than MA
Getting to work
Average commuteone way	37 minHighest 27% above MA	30 minLowest about the MA average
Work from home	21.2%±5.8Highest MA: 18.6%	13.2%±9.2Lowest MA: 18.6%
	Windsor and Middlefield 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.