Compare towns
Wellesley vs Windsor vs Winchester
Cost, people, housing, commute and schools, side by side, each benchmarked against the U.S..
What stands out worked out from the figures below
Wellesley has the most expensive homes ($1583k median).
Windsor has the most affordable homes ($305k median).
Winchester has the most kids (27.6% under 18).
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.
| Measure | Wellesley | Windsor | Winchester |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 30,347Highest |
29,468 |
23,406Lowest |
| Growth since 20102010 → 2020 census | +5.6%Lowest U.S.: +7.4% |
— | +7.5%Highest U.S.: +7.4% |
| Median age | 37.1±2.2Lowest 5% below U.S. |
43.7±1.9Highest 12% above U.S. |
42.5±1.9 9% above U.S. |
| Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 24.1%±2 U.S.: 22% |
19.2%±2.1Lowest U.S.: 22% |
27.6%±2.3Highest U.S.: 22% |
| Winchester and Wellesley are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 15.5%±1.3Lowest U.S.: 17.2% |
20%±2Highest U.S.: 17.2% |
18%±2 U.S.: 17.2% |
| Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Bachelor’s degree+adults 25+ | 89%Highest U.S.: 35.7% |
43.2%Lowest U.S.: 35.7% |
79.5% U.S.: 35.7% |
| Enrolled in collegeshare of residents | 18.3%±0.7Highest U.S.: 6.4% |
5.9%±1.3 U.S.: 6.4% |
4.9%±1.3Lowest U.S.: 6.4% |
| Cost of living | |||
| Household incomemedian | $250,001Highest 210% above U.S. |
$104,725±$8kLowest 30% above U.S. |
$230,198±$21k 185% above U.S. |
| Home valuemedian, owner-occupied | $1,582,700±$49kHighest 376% above U.S. |
$305,200±$11kLowest 8% below U.S. |
$1,215,200±$39k 265% above U.S. |
| Rentmedian gross, monthly | $2,886±$360Highest 104% above U.S. |
$1,681±$62Lowest 19% above U.S. |
$2,279±$481 61% above U.S. |
| Wellesley and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Property taxmedian, yearly | $10,000+Highest at least 221% above U.S. |
$5,351Lowest 72% above U.S. |
$10,000+Highest at least 221% above U.S. |
| Renters paying 30%+of income on rent | 44.1%±8.2 U.S.: 51.1% |
44.9%±10.9Highest U.S.: 51.1% |
39.3%±13.3Lowest U.S.: 51.1% |
| Windsor and Wellesley are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 4%Lowest U.S.: 12.5% |
6.7%Highest U.S.: 12.5% |
4.7% U.S.: 12.5% |
| Housing | |||
| Homeownersof occupied homes | 84.4%Highest U.S.: 65.2% |
82.4% U.S.: 65.2% |
81.7%Lowest U.S.: 65.2% |
| Typical home builtmedian year | 1955 25 yrs older than U.S. |
1970Highest 10 yrs older than U.S. |
1954Lowest 26 yrs older than U.S. |
| Getting to work | |||
| Average commuteone way | 27 min 3% above U.S. |
21 minLowest 19% below U.S. |
31 minHighest 19% above U.S. |
| Work from home | 32%±2.9 U.S.: 15.1% |
16.1%±3.2Lowest U.S.: 15.1% |
33.8%±3Highest U.S.: 15.1% |
| Winchester and Wellesley are within the Census margin of error here, so we can’t say which is really higher. | |||
| Schools | |||
| Public school scoresrank in state, math + reading | #6 of 282 in MA | #117 of 149 in CT | #11 of 282 in MA |
| School district | — | Capitol Region Education Council · Windsor School District | Winchester |
| High school in town | — | Windsor High School | Winchester High School |
| Students per teacherat that high school | — | 10.2Lowest |
14.8Highest |
| On TownTapestry | |||
| Old photos in History | None yet | 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.