What stands out worked out from the figures below

Guilford has the most expensive homes ($516k median).

Windsor has the most affordable homes ($305k median).

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	Guilford	Windsor
People
Population	22,108Lowest	29,468Highest
Median age	51.1±1.9Highest 24% above CT	43.7±1.9Lowest 6% above CT
Kids under 18	20.8%±2.4Highest CT: 20.2%	19.2%±2.1Lowest CT: 20.2%
	Guilford and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	26.6%±2.7Highest CT: 18.5%	20%±2Lowest CT: 18.5%
Bachelor’s degree+adults 25+	60.6%Highest CT: 42.5%	43.2%Lowest CT: 42.5%
Enrolled in collegeshare of residents	3.7%±1Lowest CT: 7.1%	5.9%±1.3Highest CT: 7.1%
	Windsor and Guilford are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$137,816±$11kHighest 44% above CT	$104,725±$8kLowest 9% above CT
Home valuemedian, owner-occupied	$515,800±$40kHighest 41% above CT	$305,200±$11kLowest 17% below CT
Rentmedian gross, monthly	$1,717±$128Highest 15% above CT	$1,681±$62Lowest 13% above CT
	Guilford and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$8,744Highest 32% above CT	$5,351Lowest 19% below CT
Renters paying 30%+of income on rent	47.4%±9Highest CT: 52.6%	44.9%±10.9Lowest CT: 52.6%
	Guilford and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	2.8%Lowest CT: 10%	6.7%Highest CT: 10%
Housing
Homeownersof occupied homes	83.7%Highest CT: 66.5%	82.4%Lowest CT: 66.5%
Typical home builtmedian year	1974Highest 7 yrs newer than CT	1970Lowest 3 yrs newer than CT
Getting to work
Average commuteone way	26 minHighest about the CT average	21 minLowest 19% below CT
Work from home	21.7%±3.3Highest CT: 16%	16.1%±3.2Lowest CT: 16%
	Guilford 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	#15 of 149 in CT	#117 of 149 in CT
School district	Guilford School District	Capitol Region Education Council · Windsor School District
High school in town	Guilford High School	Windsor High School
Students per teacherat that high school	11.8Highest	10.2Lowest
On TownTapestry
Old photos in History	None yet	None yet

CT 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.