What stands out worked out from the figures below

Pomfret has the most affordable homes ($409k median).

Winchester has the most expensive homes ($1215k 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	Pomfret	Winchester
People
Population	4,317Lowest	23,406Highest
Growth since 20102010 → 2020 census	—	+7.5% U.S.: +7.4%
Median age	45.9±3.7Highest 18% above U.S.	42.5±1.9Lowest 9% above U.S.
	Pomfret and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18	23.1%±4.9Lowest U.S.: 22%	27.6%±2.3Highest U.S.: 22%
	Winchester and Pomfret are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	17.8%±4.5Lowest U.S.: 17.2%	18%±2Highest U.S.: 17.2%
	Winchester and Pomfret are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+	50.8%Lowest U.S.: 35.7%	79.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	5.6%±1.9Highest U.S.: 6.4%	4.9%±1.3Lowest U.S.: 6.4%
	Pomfret and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$108,476±$8kLowest 34% above U.S.	$230,198±$21kHighest 185% above U.S.
Home valuemedian, owner-occupied	$409,100±$28kLowest 23% above U.S.	$1,215,200±$39kHighest 265% above U.S.
Rentmedian gross, monthly	$1,210±$300Lowest 14% below U.S.	$2,279±$481Highest 61% above U.S.
Property taxmedian, yearly	$5,903Lowest 89% above U.S.	$10,000+Highest at least 221% above U.S.
Renters paying 30%+of income on rent	61.9%±15.3Highest U.S.: 51.1%	39.3%±13.3Lowest U.S.: 51.1%
	Pomfret and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	6%Highest U.S.: 12.5%	4.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	80.5%Lowest U.S.: 65.2%	81.7%Highest U.S.: 65.2%
Typical home builtmedian year	1978Highest 2 yrs older than U.S.	1954Lowest 26 yrs older than U.S.
Getting to work
Average commuteone way	24 minLowest 11% below U.S.	31 minHighest 19% above U.S.
Work from home	13.2%±5.2Lowest U.S.: 15.1%	33.8%±3Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#39 of 149 in CT	#11 of 282 in MA
School district	Pomfret School District	Winchester
High school in town	None in town	Winchester High School
Students per teacherat that high school	—	14.8
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.