Compare towns

Windsor vs Everett vs Cheshire 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%).
Everett has grown the fastest since 2010 (+17.8%).
Cheshire has the most affordable homes ($268k median).
Montgomery has the highest household income ($123k).

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.

MeasureWindsorEverettCheshireMontgomery
People
Population
1,065
50,045Highest
3,216
796Lowest
Growth since 20102010 → 2020 census
-7.6%Lowest
MA: +7.4%
+17.8%Highest
MA: +7.4%
+0.7%
MA: +7.4%
-2.3%
MA: +7.4%
Median age
44.8±6.4
12% above MA
35.2±1.5Lowest
12% below MA
53.7±4.5Highest
34% above MA
49.7±5.8
24% above MA
Cheshire and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
Kids under 18
15.8%±5.1
MA: 19.4%
21.8%±2.1
MA: 19.4%
15.3%±4.2Lowest
MA: 19.4%
22%±5.8Highest
MA: 19.4%
Montgomery and Everett are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
18.6%±4.9
MA: 17.9%
11.3%±1.1Lowest
MA: 17.9%
30.5%±7.1Highest
MA: 17.9%
24.9%±7
MA: 17.9%
Cheshire and Montgomery are within the Census margin of error here, so we can’t say which is really higher.
Bachelor’s degree+adults 25+
41.5%Highest
MA: 47.3%
24.9%Lowest
MA: 47.3%
26.9%
MA: 47.3%
38.1%
MA: 47.3%
Enrolled in collegeshare of residents
2.7%±1.7Lowest
MA: 7.9%
6.3%±0.9Highest
MA: 7.9%
5%±2.5
MA: 7.9%
4.3%±1.6
MA: 7.9%
Everett and Cheshire are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$115,563±$10k
11% above MA
$85,218±$7k
18% below MA
$69,803±$14kLowest
33% below MA
$123,000±$19kHighest
18% above MA
Montgomery and Windsor 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
$610,000±$23kHighest
9% above MA
$268,200±$48kLowest
52% below MA
$357,500±$29k
36% below MA
Rentmedian gross, monthly —
$2,076±$69
18% above MA
— —
Property taxmedian, yearly
$3,867
35% below MA
$4,880Highest
19% below MA
$3,005Lowest
50% below MA
$4,283
29% below MA
Renters paying 30%+of income on rent
0%±100Lowest
MA: 51.8%
56.4%±5.8Highest
MA: 51.8%
21.2%±24
MA: 51.8%
50%±100
MA: 51.8%
Everett 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%
14.7%Highest
MA: 10%
8.6%
MA: 10%
1.5%Lowest
MA: 10%
Housing
Homeownersof occupied homes
96.2%
MA: 62.5%
37.2%Lowest
MA: 62.5%
89%
MA: 62.5%
96.3%Highest
MA: 62.5%
Typical home builtmedian year
1970
6 yrs newer than MA
1938Lowest
26 yrs older than MA
1964
same as MA
1978Highest
14 yrs newer than MA
Getting to work
Average commuteone way
37 minHighest
27% above MA
35 min
20% above MA
29 minLowest
about the MA average
36 min
23% above MA
Work from home
21.2%±5.8Highest
MA: 18.6%
10.5%±2
MA: 18.6%
4.4%±2.7Lowest
MA: 18.6%
9.4%±6
MA: 18.6%
Schools
Public school scoresrank in state, math + reading — #264 of 282 in MA #274 of 282 in MA —
School district — Everett Hoosac Valley Regional —
High school in town — Everett High Hoosac Valley High School —
Students per teacherat that high school —
12.1Highest
10.5Lowest
—
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.