What stands out worked out from the figures below

Windsor has the most kids (23.2% under 18).

Wolfeboro has the most people working from home (22.9%).

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	Windsor	Wolfeboro
People
Population	2,690Lowest	6,571Highest
Growth since 20102010 → 2020 census	+2.2%Lowest U.S.: +7.4%	+2.3%Highest U.S.: +7.4%
Median age	43.5±8Lowest 12% above U.S.	57±1.8Highest 47% above U.S.
Kids under 18	23.2%±6.4Highest U.S.: 22%	13.7%±3.3Lowest U.S.: 22%
	Windsor and Wolfeboro are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	14.3%±4.4Lowest U.S.: 17.2%	34.6%±5.2Highest U.S.: 17.2%
Bachelor’s degree+adults 25+	21%Lowest U.S.: 35.7%	45%Highest U.S.: 35.7%
Enrolled in collegeshare of residents	2%±1.6Lowest U.S.: 6.4%	2.8%±1.8Highest U.S.: 6.4%
	Wolfeboro and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$63,178±$5kLowest 22% below U.S.	$94,375±$22kHighest 17% above U.S.
Home valuemedian, owner-occupied	$228,800±$22kLowest 31% below U.S.	$546,500±$60kHighest 64% above U.S.
Rentmedian gross, monthly	$1,265±$400Highest 10% below U.S.	$1,103±$76Lowest 22% below U.S.
	Windsor and Wolfeboro are within the Census margin of error here, so we can’t say which is really higher.
Property taxmedian, yearly	$2,160Lowest 31% below U.S.	$4,531Highest 45% above U.S.
Renters paying 30%+of income on rent	46.2%±31.6Highest U.S.: 51.1%	12%±11.6Lowest U.S.: 51.1%
	Windsor and Wolfeboro are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	7.5%Lowest U.S.: 12.5%	8.2%Highest U.S.: 12.5%
Housing
Homeownersof occupied homes	89.1%Highest U.S.: 65.2%	78.1%Lowest U.S.: 65.2%
Typical home builtmedian year	1986Highest 6 yrs newer than U.S.	1982Lowest 2 yrs newer than U.S.
Getting to work
Average commuteone way	36 minHighest 35% above U.S.	24 minLowest 10% below U.S.
Work from home	6.5%±3Lowest U.S.: 15.1%	22.9%±6.6Highest U.S.: 15.1%
Schools
Public school scoresrank in state, math + reading	#44 of 133 in ME	#46 of 120 in NH
School district	RSU 12	Governor Wentworth Regional School District
High school in town	None in town	Kingswood Regional High School
Students per teacherat that high school	—	11.1
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.