Compare towns

Windsor vs Weston 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 youngest population (median age 44.8).
Weston has the most expensive homes ($1694k median).
Montgomery has the oldest population (median age 49.7).

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.

MeasureWindsorWestonMontgomery
People
Population
1,065
11,579Highest
796Lowest
Growth since 20102010 → 2020 census
-7.6%Lowest
MA: +7.4%
+5.2%Highest
MA: +7.4%
-2.3%
MA: +7.4%
Median age
44.8±6.4Lowest
12% above MA
44.9±2.1
12% above MA
49.7±5.8Highest
24% above MA
Montgomery and Weston 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%
26%±3.8Highest
MA: 19.4%
22%±5.8
MA: 19.4%
Weston and Montgomery 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%
20%±2.8
MA: 17.9%
24.9%±7Highest
MA: 17.9%
Montgomery and Weston 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%
84.3%Highest
MA: 47.3%
38.1%Lowest
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
9.8%±1.6Highest
MA: 7.9%
4.3%±1.6
MA: 7.9%
Cost of living
Household incomemedian
$115,563±$10kLowest
11% above MA
$250,001Highest
140% above MA
$123,000±$19k
18% above MA
Home valuemedian, owner-occupied
$389,700±$32k
31% below MA
$1,694,400±$263kHighest
201% above MA
$357,500±$29kLowest
36% below MA
Rentmedian gross, monthly —
$2,085±$809
18% above MA
—
Property taxmedian, yearly
$3,867Lowest
35% below MA
$10,000+Highest
at least 67% above MA
$4,283
29% below MA
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
69%±23Highest
MA: 51.8%
50%±100
MA: 51.8%
Weston and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
3.8%Highest
MA: 10%
2.9%
MA: 10%
1.5%Lowest
MA: 10%
Housing
Homeownersof occupied homes
96.2%
MA: 62.5%
87.5%Lowest
MA: 62.5%
96.3%Highest
MA: 62.5%
Typical home builtmedian year
1970
6 yrs newer than MA
1964Lowest
same as MA
1978Highest
14 yrs newer than MA
Getting to work
Average commuteone way
37 minHighest
27% above MA
27 minLowest
8% below MA
36 min
23% above MA
Work from home
21.2%±5.8
MA: 18.6%
29.1%±5.2Highest
MA: 18.6%
9.4%±6Lowest
MA: 18.6%
Weston and Windsor 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 — #9 of 282 in MA —
School district — Weston —
High school in town — Weston High —
Students per teacherat that high school —
10.9
—
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.