Compare towns

Dover vs Winchester vs Weston

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

What stands out worked out from the figures below

Dover has the most homeowners (97.9%).
Winchester has grown the fastest since 2010 (+7.5%).
Weston has the most expensive homes ($1694k 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.

MeasureDoverWinchesterWeston
People
Population
5,930Lowest
23,406Highest
11,579
Growth since 20102010 → 2020 census
+6%
MA: +7.4%
+7.5%Highest
MA: +7.4%
+5.2%Lowest
MA: +7.4%
Median age
44.9±2.3Highest
12% above MA
42.5±1.9Lowest
6% above MA
44.9±2.1Highest
12% above MA
Kids under 18
26%±5.2Lowest
MA: 19.4%
27.6%±2.3Highest
MA: 19.4%
26%±3.8Lowest
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+
16.7%±2.9Lowest
MA: 17.9%
18%±2
MA: 17.9%
20%±2.8Highest
MA: 17.9%
Weston and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
84.8%Highest
MA: 47.3%
79.5%Lowest
MA: 47.3%
84.3%
MA: 47.3%
Enrolled in collegeshare of residents
7.2%±2.7
MA: 7.9%
4.9%±1.3Lowest
MA: 7.9%
9.8%±1.6Highest
MA: 7.9%
Weston and Dover are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$250,001Highest
140% above MA
$230,198±$21kLowest
121% above MA
$250,001Highest
140% above MA
Home valuemedian, owner-occupied
$1,340,300±$117k
138% above MA
$1,215,200±$39kLowest
116% above MA
$1,694,400±$263kHighest
201% above MA
Weston and Dover are within the Census margin of error here, so we can’t say which is really higher.
Rentmedian gross, monthly
$2,917±$2kHighest
66% above MA
$2,279±$481
29% above MA
$2,085±$809Lowest
18% above 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+
at least 67% above MA
$10,000+
at least 67% above MA
$10,000+
at least 67% above MA
Renters paying 30%+of income on rent
20%±100Lowest
MA: 51.8%
39.3%±13.3
MA: 51.8%
69%±23Highest
MA: 51.8%
Weston and Winchester are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
2.7%Lowest
MA: 10%
4.7%Highest
MA: 10%
2.9%
MA: 10%
Housing
Homeownersof occupied homes
97.9%Highest
MA: 62.5%
81.7%Lowest
MA: 62.5%
87.5%
MA: 62.5%
Typical home builtmedian year
1970Highest
6 yrs newer than MA
1954Lowest
10 yrs older than MA
1964
same as MA
Getting to work
Average commuteone way
35 minHighest
19% above MA
31 min
8% above MA
27 minLowest
8% below MA
Work from home
34.2%±6.4Highest
MA: 18.6%
33.8%±3
MA: 18.6%
29.1%±5.2Lowest
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 #1 of 282 in MA #11 of 282 in MA #9 of 282 in MA
School district Dover · Dover-Sherborn Winchester Weston
High school in town Dover-Sherborn Regional High Winchester High School Weston High
Students per teacherat that high school
9.8Lowest
14.8Highest
10.9
On TownTapestry
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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.