Compare towns
Winchester vs Windsor vs Milton
Cost, people, housing, commute and schools, side by side, each benchmarked against Massachusetts.
What stands out worked out from the figures below
Winchester has the most expensive homes ($1215k median).
Windsor has the most affordable homes ($390k median).
Milton has the youngest population (median age 41.1).
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 | Winchester | Windsor | Milton |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 23,406 |
1,065Lowest |
28,587Highest |
| Growth since 20102010 → 2020 census | +7.5%Highest MA: +7.4% |
-7.6%Lowest MA: +7.4% |
+6% MA: +7.4% |
| Median age | 42.5±1.9 6% above MA |
44.8±6.4Highest 12% above MA |
41.1±1.8Lowest about the MA average |
| Windsor and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Kids under 18 | 27.6%±2.3Highest MA: 19.4% |
15.8%±5.1Lowest MA: 19.4% |
25.3%±2.2 MA: 19.4% |
| Winchester and Milton are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 18%±2 MA: 17.9% |
18.6%±4.9Highest MA: 17.9% |
16.1%±1.8Lowest MA: 17.9% |
| 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+ | 79.5%Highest MA: 47.3% |
41.5%Lowest MA: 47.3% |
71.9% MA: 47.3% |
| Enrolled in collegeshare of residents | 4.9%±1.3 MA: 7.9% |
2.7%±1.7Lowest MA: 7.9% |
9.7%±1.1Highest MA: 7.9% |
| Cost of living | |||
| Household incomemedian | $230,198±$21kHighest 121% above MA |
$115,563±$10kLowest 11% above MA |
$188,529±$15k 81% above MA |
| Home valuemedian, owner-occupied | $1,215,200±$39kHighest 116% above MA |
$389,700±$32kLowest 31% below MA |
$933,200±$31k 66% above MA |
| Rentmedian gross, monthly | $2,279±$481Highest 29% above MA |
— | $1,474±$281Lowest 16% below MA |
| Property taxmedian, yearly | $10,000+Highest at least 67% above MA |
$3,867Lowest 35% below MA |
$9,677 61% above MA |
| Renters paying 30%+of income on rent | 39.3%±13.3 MA: 51.8% |
0%±100Lowest MA: 51.8% |
45.7%±20.9Highest MA: 51.8% |
| Milton and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 4.7%Highest MA: 10% |
3.8%Lowest MA: 10% |
4.7%Highest MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 81.7%Lowest MA: 62.5% |
96.2%Highest MA: 62.5% |
85.2% MA: 62.5% |
| Typical home builtmedian year | 1954 10 yrs older than MA |
1970Highest 6 yrs newer than MA |
1945Lowest 19 yrs older than MA |
| Getting to work | |||
| Average commuteone way | 31 min 8% above MA |
37 minHighest 27% above MA |
31 minLowest 8% above MA |
| Work from home | 33.8%±3Highest MA: 18.6% |
21.2%±5.8Lowest MA: 18.6% |
29.7%±2.9 MA: 18.6% |
| Winchester and Milton 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 | #11 of 282 in MA | — | #55 of 282 in MA |
| School district | Winchester | — | Milton |
| High school in town | Winchester High School | — | Milton High |
| Students per teacherat that high school | 14.8Highest |
— | 12.4Lowest |
| 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.