Compare towns

Wellesley vs Windsor vs Wellesley

Cost, people, housing, commute and schools, side by side, each benchmarked against Massachusetts.

What stands out worked out from the figures below

Windsor has the most affordable homes ($390k 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.

MeasureWellesleyWindsorWellesley
People
Population
30,347Highest
1,065Lowest
30,347Highest
Growth since 20102010 → 2020 census
+5.6%Highest
MA: +7.4%
-7.6%Lowest
MA: +7.4%
+5.6%Highest
MA: +7.4%
Median age
37.1±2.2Lowest
7% below MA
44.8±6.4Highest
12% above MA
37.1±2.2Lowest
7% below MA
Windsor and Wellesley are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
24.1%±2Highest
MA: 19.4%
15.8%±5.1Lowest
MA: 19.4%
24.1%±2Highest
MA: 19.4%
Age 65+
15.5%±1.3Lowest
MA: 17.9%
18.6%±4.9Highest
MA: 17.9%
15.5%±1.3Lowest
MA: 17.9%
Windsor and Wellesley are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
89%Highest
MA: 47.3%
41.5%Lowest
MA: 47.3%
89%Highest
MA: 47.3%
Enrolled in collegeshare of residents
18.3%±0.7Highest
MA: 7.9%
2.7%±1.7Lowest
MA: 7.9%
18.3%±0.7Highest
MA: 7.9%
Cost of living
Household incomemedian
$250,001Highest
140% above MA
$115,563±$10kLowest
11% above MA
$250,001Highest
140% above MA
Home valuemedian, owner-occupied
$1,582,700±$49kHighest
182% above MA
$389,700±$32kLowest
31% below MA
$1,582,700±$49kHighest
182% above MA
Rentmedian gross, monthly
$2,886±$360
64% above MA
—
$2,886±$360
64% above MA
Property taxmedian, yearly
$10,000+Highest
at least 67% above MA
$3,867Lowest
35% below MA
$10,000+Highest
at least 67% above MA
Renters paying 30%+of income on rent
44.1%±8.2Highest
MA: 51.8%
0%±100Lowest
MA: 51.8%
44.1%±8.2Highest
MA: 51.8%
Below poverty line
4%Highest
MA: 10%
3.8%Lowest
MA: 10%
4%Highest
MA: 10%
Housing
Homeownersof occupied homes
84.4%Lowest
MA: 62.5%
96.2%Highest
MA: 62.5%
84.4%Lowest
MA: 62.5%
Typical home builtmedian year
1955Lowest
9 yrs older than MA
1970Highest
6 yrs newer than MA
1955Lowest
9 yrs older than MA
Getting to work
Average commuteone way
27 minLowest
7% below MA
37 minHighest
27% above MA
27 minLowest
7% below MA
Work from home
32%±2.9Highest
MA: 18.6%
21.2%±5.8Lowest
MA: 18.6%
32%±2.9Highest
MA: 18.6%
Schools
Public school scoresrank in state, math + reading #6 of 282 in MA — #6 of 282 in MA
School district — — Wellesley
High school in town — — Wellesley Sr High
Students per teacherat that high school — —
10.8
On TownTapestry
Old photos in History None yet None yet None yet

MA 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.