What stands out worked out from the figures below

Thompson has the most affordable homes ($292k 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	Thompson	Winchester
People
Population	9,337Lowest	23,406Highest
Growth since 20102010 → 2020 census	—	+7.5% U.S.: +7.4%
Median age	54.1±2.2Highest 39% above U.S.	42.5±1.9Lowest 9% above U.S.
Kids under 18	11.4%±2.8Lowest U.S.: 22%	27.6%±2.3Highest U.S.: 22%
Age 65+	24.4%±4.3Highest U.S.: 17.2%	18%±2Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	21.9%Lowest U.S.: 35.7%	79.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	2.9%±1.3Lowest U.S.: 6.4%	4.9%±1.3Highest U.S.: 6.4%
	Winchester and Thompson are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$93,629±$18kLowest 16% above U.S.	$230,198±$21kHighest 185% above U.S.
Home valuemedian, owner-occupied	$291,900±$24kLowest 12% below U.S.	$1,215,200±$39kHighest 265% above U.S.
Rentmedian gross, monthly	$1,012±$344Lowest 28% below U.S.	$2,279±$481Highest 61% above U.S.
Property taxmedian, yearly	$3,822Lowest 23% above U.S.	$10,000+Highest at least 221% above U.S.
Renters paying 30%+of income on rent	54%±18.7Highest U.S.: 51.1%	39.3%±13.3Lowest U.S.: 51.1%
	Thompson and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	5.9%Highest U.S.: 12.5%	4.7%Lowest U.S.: 12.5%
Housing
Homeownersof occupied homes	84.3%Highest U.S.: 65.2%	81.7%Lowest U.S.: 65.2%
Typical home builtmedian year	1963Highest 17 yrs older than U.S.	1954Lowest 26 yrs older than U.S.
Getting to work
Average commuteone way	32 minHighest 20% above U.S.	31 minLowest 19% above U.S.
Work from home	13.1%±4.4Lowest U.S.: 15.1%	33.8%±3Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#130 of 149 in CT	#11 of 282 in MA
School district	Thompson School District	Winchester
High school in town	Tourtellotte Memorial High School	Winchester High School
Students per teacherat that high school	7.9Lowest	14.8Highest
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.