Compare towns

Winchester vs Sutton 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).
Sutton has the most affordable homes ($523k 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.

MeasureWinchesterSuttonMilton
People
Population
23,406
9,452Lowest
28,587Highest
Growth since 20102010 → 2020 census
+7.5%Highest
MA: +7.4%
+4.4%Lowest
MA: +7.4%
+6%
MA: +7.4%
Median age
42.5±1.9
6% above MA
44.3±2.5Highest
11% above MA
41.1±1.8Lowest
about the MA average
Sutton 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%
19.6%±3.3Lowest
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%
18.8%±3.2Highest
MA: 17.9%
16.1%±1.8Lowest
MA: 17.9%
Sutton 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%
52.8%Lowest
MA: 47.3%
71.9%
MA: 47.3%
Enrolled in collegeshare of residents
4.9%±1.3
MA: 7.9%
3.9%±1.8Lowest
MA: 7.9%
9.7%±1.1Highest
MA: 7.9%
Cost of living
Household incomemedian
$230,198±$21kHighest
121% above MA
$147,125±$25kLowest
42% above MA
$188,529±$15k
81% above MA
Home valuemedian, owner-occupied
$1,215,200±$39kHighest
116% above MA
$523,100±$47kLowest
7% below MA
$933,200±$31k
66% above MA
Rentmedian gross, monthly
$2,279±$481Highest
29% above MA
$1,190±$401Lowest
32% below MA
$1,474±$281
16% below MA
Property taxmedian, yearly
$10,000+Highest
at least 67% above MA
$6,763Lowest
13% above MA
$9,677
61% above MA
Renters paying 30%+of income on rent
39.3%±13.3Lowest
MA: 51.8%
47.5%±24.4Highest
MA: 51.8%
45.7%±20.9
MA: 51.8%
Sutton and Milton are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
4.7%Lowest
MA: 10%
5.8%Highest
MA: 10%
4.7%Lowest
MA: 10%
Housing
Homeownersof occupied homes
81.7%Lowest
MA: 62.5%
89.7%Highest
MA: 62.5%
85.2%
MA: 62.5%
Typical home builtmedian year
1954
10 yrs older than MA
1981Highest
17 yrs newer than MA
1945Lowest
19 yrs older than MA
Getting to work
Average commuteone way
31 minHighest
8% above MA
30 minLowest
about the MA average
31 min
8% above MA
Work from home
33.8%±3Highest
MA: 18.6%
22.7%±4.1Lowest
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 #105 of 282 in MA #55 of 282 in MA
School district Winchester Sutton Milton
High school in town Winchester High School Sutton High School Milton High
Students per teacherat that high school
14.8Highest
12.6
12.4Lowest
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.