Compare towns
Winchester vs Winchester vs Milton
Cost, people, housing, commute and schools, side by side, each benchmarked against Massachusetts.
What stands out worked out from the figures below
Milton has the most affordable homes ($933k 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.
| Measure | Winchester | Winchester | Milton |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 23,406Lowest |
23,406Lowest |
28,587Highest |
| Growth since 20102010 → 2020 census | +7.5%Highest MA: +7.4% |
+7.5%Highest MA: +7.4% |
+6%Lowest MA: +7.4% |
| Median age | 42.5±1.9Highest 6% above MA |
42.5±1.9Highest 6% above MA |
41.1±1.8Lowest about the MA average |
| Kids under 18 | 27.6%±2.3Highest MA: 19.4% |
27.6%±2.3Highest MA: 19.4% |
25.3%±2.2Lowest MA: 19.4% |
| Age 65+ | 18%±2Highest MA: 17.9% |
18%±2Highest MA: 17.9% |
16.1%±1.8Lowest MA: 17.9% |
| Bachelor’s degree+adults 25+ | 79.5%Highest MA: 47.3% |
79.5%Highest MA: 47.3% |
71.9%Lowest MA: 47.3% |
| Enrolled in collegeshare of residents | 4.9%±1.3Lowest MA: 7.9% |
4.9%±1.3Lowest MA: 7.9% |
9.7%±1.1Highest MA: 7.9% |
| Cost of living | |||
| Household incomemedian | $230,198±$21kHighest 121% above MA |
$230,198±$21kHighest 121% above MA |
$188,529±$15kLowest 81% above MA |
| Home valuemedian, owner-occupied | $1,215,200±$39kHighest 116% above MA |
$1,215,200±$39kHighest 116% above MA |
$933,200±$31kLowest 66% above MA |
| Rentmedian gross, monthly | $2,279±$481Highest 29% above MA |
$2,279±$481Highest 29% above MA |
$1,474±$281Lowest 16% below MA |
| Property taxmedian, yearly | $10,000+Highest at least 67% above MA |
$10,000+Highest at least 67% above MA |
$9,677Lowest 61% above MA |
| Renters paying 30%+of income on rent | 39.3%±13.3Lowest MA: 51.8% |
39.3%±13.3Lowest 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% MA: 10% |
4.7% MA: 10% |
4.7% MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 81.7%Lowest MA: 62.5% |
81.7%Lowest MA: 62.5% |
85.2%Highest MA: 62.5% |
| Typical home builtmedian year | 1954Highest 10 yrs older than MA |
1954Highest 10 yrs older than MA |
1945Lowest 19 yrs older than MA |
| Getting to work | |||
| Average commuteone way | 31 minHighest 8% above MA |
31 minHighest 8% above MA |
31 minLowest 8% above MA |
| Work from home | 33.8%±3Highest MA: 18.6% |
33.8%±3Highest MA: 18.6% |
29.7%±2.9Lowest MA: 18.6% |
| Schools | |||
| Public school scoresrank in state, math + reading | #11 of 282 in MA | #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.