Compare towns
Winchester vs Dover 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 grown the fastest since 2010 (+7.5%).
Dover has the most homeowners (97.9%).
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 | Dover | Milton |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 23,406 |
5,930Lowest |
28,587Highest |
| Growth since 20102010 → 2020 census | +7.5%Highest MA: +7.4% |
+6%Lowest MA: +7.4% |
+6%Lowest MA: +7.4% |
| Median age | 42.5±1.9 6% above MA |
44.9±2.3Highest 12% above MA |
41.1±1.8Lowest about the MA average |
| Dover 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% |
26%±5.2 MA: 19.4% |
25.3%±2.2Lowest MA: 19.4% |
| Winchester and Dover are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 18%±2Highest MA: 17.9% |
16.7%±2.9 MA: 17.9% |
16.1%±1.8Lowest MA: 17.9% |
| Winchester and Dover are within the Census margin of error here, so we can’t say which is really higher. | |||
| Bachelor’s degree+adults 25+ | 79.5% MA: 47.3% |
84.8%Highest MA: 47.3% |
71.9%Lowest MA: 47.3% |
| Enrolled in collegeshare of residents | 4.9%±1.3Lowest MA: 7.9% |
7.2%±2.7 MA: 7.9% |
9.7%±1.1Highest MA: 7.9% |
| Milton and Dover are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $230,198±$21k 121% above MA |
$250,001Highest 140% above MA |
$188,529±$15kLowest 81% above MA |
| Home valuemedian, owner-occupied | $1,215,200±$39k 116% above MA |
$1,340,300±$117kHighest 138% above MA |
$933,200±$31kLowest 66% above MA |
| Dover and Winchester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Rentmedian gross, monthly | $2,279±$481 29% above MA |
$2,917±$2kHighest 66% above MA |
$1,474±$281Lowest 16% below MA |
| Dover 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 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%±13.3 MA: 51.8% |
20%±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% |
2.7%Lowest MA: 10% |
4.7%Highest MA: 10% |
| Housing | |||
| Homeownersof occupied homes | 81.7%Lowest MA: 62.5% |
97.9%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 |
35 minHighest 19% above MA |
31 minLowest 8% above MA |
| Work from home | 33.8%±3 MA: 18.6% |
34.2%±6.4Highest MA: 18.6% |
29.7%±2.9Lowest MA: 18.6% |
| Dover and Winchester 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 | #1 of 282 in MA | #55 of 282 in MA |
| School district | Winchester | Dover · Dover-Sherborn | Milton |
| High school in town | Winchester High School | Dover-Sherborn Regional High | Milton High |
| Students per teacherat that high school | 14.8Highest |
9.8Lowest |
12.4 |
| 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.