Compare towns

Windsor vs Dedham vs Montgomery

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

What stands out worked out from the figures below

Windsor has the most people working from home (21.2%).
Dedham has grown the fastest since 2010 (+2.6%).
Montgomery has the most kids (22% under 18).

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.

MeasureWindsorDedhamMontgomery
People
Population
1,065
25,237Highest
796Lowest
Growth since 20102010 → 2020 census
-7.6%Lowest
MA: +7.4%
+2.6%Highest
MA: +7.4%
-2.3%
MA: +7.4%
Median age
44.8±6.4
12% above MA
44.6±1.6Lowest
12% above MA
49.7±5.8Highest
24% above MA
Montgomery and Windsor are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
15.8%±5.1Lowest
MA: 19.4%
18.6%±1.9
MA: 19.4%
22%±5.8Highest
MA: 19.4%
Montgomery and Dedham are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
18.6%±4.9Lowest
MA: 17.9%
21.9%±2
MA: 17.9%
24.9%±7Highest
MA: 17.9%
Montgomery and Dedham are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
41.5%
MA: 47.3%
55%Highest
MA: 47.3%
38.1%Lowest
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
5.6%±1Highest
MA: 7.9%
4.3%±1.6
MA: 7.9%
Dedham and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$115,563±$10kLowest
11% above MA
$128,955±$10kHighest
24% above MA
$123,000±$19k
18% above MA
Dedham and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
Home valuemedian, owner-occupied
$389,700±$32k
31% below MA
$661,800±$16kHighest
18% above MA
$357,500±$29kLowest
36% below MA
Rentmedian gross, monthly —
$2,042±$182
16% above MA
—
Property taxmedian, yearly
$3,867Lowest
35% below MA
$7,918Highest
32% above MA
$4,283
29% below MA
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
56.4%±10Highest
MA: 51.8%
50%±100
MA: 51.8%
Dedham and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.8%
MA: 10%
5.6%Highest
MA: 10%
1.5%Lowest
MA: 10%
Housing
Homeownersof occupied homes
96.2%
MA: 62.5%
73.4%Lowest
MA: 62.5%
96.3%Highest
MA: 62.5%
Typical home builtmedian year
1970
6 yrs newer than MA
1956Lowest
8 yrs older than MA
1978Highest
14 yrs newer than MA
Getting to work
Average commuteone way
37 minHighest
27% above MA
29 minLowest
about the MA average
36 min
23% above MA
Work from home
21.2%±5.8Highest
MA: 18.6%
20%±2.7
MA: 18.6%
9.4%±6Lowest
MA: 18.6%
Windsor and Dedham 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 — #119 of 282 in MA —
School district — Dedham —
High school in town — Dedham High —
Students per teacherat that high school —
10.4
—
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.