What stands out worked out from the figures below

Rupert has the most affordable homes ($363k median).

Winchester has grown the fastest since 2010 (+7.5%).

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	Rupert	Winchester
People
Population	676Lowest	23,406Highest
Growth since 20102010 → 2020 census	-2.2%Lowest U.S.: +7.4%	+7.5%Highest U.S.: +7.4%
Median age	57.8±9.7Highest 49% above U.S.	42.5±1.9Lowest 9% above U.S.
Kids under 18	13.9%±3.7Lowest U.S.: 22%	27.6%±2.3Highest U.S.: 22%
Age 65+	42.3%±8.1Highest U.S.: 17.2%	18%±2Lowest U.S.: 17.2%
Bachelor’s degree+adults 25+	30.6%Lowest U.S.: 35.7%	79.5%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	2.1%±2.5Lowest U.S.: 6.4%	4.9%±1.3Highest U.S.: 6.4%
	Winchester and Rupert are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$88,229±$36kLowest 9% above U.S.	$230,198±$21kHighest 185% above U.S.
Home valuemedian, owner-occupied	$362,500±$63kLowest 9% above U.S.	$1,215,200±$39kHighest 265% above U.S.
Rentmedian gross, monthly	—	$2,279±$481 61% above U.S.
Property taxmedian, yearly	$4,594Lowest 47% above U.S.	$10,000+Highest at least 221% above U.S.
Renters paying 30%+of income on rent	20%±100Lowest U.S.: 51.1%	39.3%±13.3Highest U.S.: 51.1%
	Winchester and Rupert 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	93.7%Highest U.S.: 65.2%	81.7%Lowest U.S.: 65.2%
Typical home builtmedian year	1955Highest 25 yrs older than U.S.	1954Lowest 26 yrs older than U.S.
Getting to work
Average commuteone way	27 minLowest about the U.S. average	31 minHighest 19% above U.S.
Work from home	18.6%±9.2Lowest U.S.: 15.1%	33.8%±3Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	—	#11 of 282 in MA
School district	—	Winchester
High school 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.