What stands out worked out from the figures below

Brookfield has the most people working from home (16.3%).

Winchester has the most affordable homes ($250k 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	Brookfield	Winchester
People
Population	17,706Highest	10,284Lowest
Median age	44.3±1.8Lowest 8% above CT	49.1±6.2Highest 19% above CT
	Winchester and Brookfield are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	22.7%±3Highest CT: 20.2%	15.4%±2.9Lowest CT: 20.2%
Age 65+	18.8%±2.8Lowest CT: 18.5%	27.4%±5.1Highest CT: 18.5%
Bachelor’s degree+adults 25+	58.3%Highest CT: 42.5%	27.8%Lowest CT: 42.5%
Enrolled in collegeshare of residents	4.3%±1.4Highest CT: 7.1%	4.2%±1.7Lowest CT: 7.1%
	Brookfield and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$148,360±$11kHighest 55% above CT	$66,519±$12kLowest 31% below CT
Home valuemedian, owner-occupied	$479,700±$24kHighest 31% above CT	$249,500±$17kLowest 32% below CT
Rentmedian gross, monthly	$1,892±$183Highest 27% above CT	$1,174±$116Lowest 21% below CT
Property taxmedian, yearly	$7,594Highest 14% above CT	$4,780Lowest 28% below CT
Renters paying 30%+of income on rent	35.9%±13.1Lowest CT: 52.6%	48.9%±15.8Highest CT: 52.6%
	Winchester and Brookfield are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	4.1%Lowest CT: 10%	12.8%Highest CT: 10%
Housing
Homeownersof occupied homes	86.5%Highest CT: 66.5%	65.8%Lowest CT: 66.5%
Typical home builtmedian year	1978Highest 11 yrs newer than CT	1955Lowest 12 yrs older than CT
Getting to work
Average commuteone way	28 minHighest 6% above CT	26 minLowest about the CT average
Work from home	16.3%±3Highest CT: 16%	6.9%±2.7Lowest CT: 16%
Schools
Public school scoresrank in state, math + reading	#67 of 149 in CT	#97 of 149 in CT
School district	Brookfield School District	Explorations District · Regional School District 07
High school in town	Brookfield High School	Northwestern Regional High School
Students per teacherat that high school	12.7Highest	9.7Lowest
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.