Compare towns

Weston vs Madison vs Westport

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

What stands out worked out from the figures below

Weston has the most people working from home (44.9%).
Madison has the most affordable homes ($584k median).
Westport has the most expensive homes ($1405k 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.

MeasureWestonMadisonWestport
People
Population
10,396Lowest
17,616
27,528Highest
Median age
45.7±2.7
11% above CT
51.9±1.9Highest
26% above CT
45.4±1.5Lowest
10% above CT
Kids under 18
26.4%±3.2
CT: 20.2%
18.1%±2.2Lowest
CT: 20.2%
27.9%±2.7Highest
CT: 20.2%
Westport and Weston are within the Census margin of error here, so we can’t say which is really higher.
Age 65+
17.3%±2.4Lowest
CT: 18.5%
25.2%±2.4Highest
CT: 18.5%
18.5%±1.8
CT: 18.5%
Bachelor’s degree+adults 25+
83.7%Highest
CT: 42.5%
72.4%Lowest
CT: 42.5%
79.9%
CT: 42.5%
Enrolled in collegeshare of residents
5.3%±2.2
CT: 7.1%
5.9%±1.5Highest
CT: 7.1%
3.2%±0.8Lowest
CT: 7.1%
Madison and Weston are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian
$250,001Highest
161% above CT
$167,442±$16kLowest
75% above CT
$250,001Highest
161% above CT
Home valuemedian, owner-occupied
$996,700±$52k
172% above CT
$583,900±$30kLowest
59% above CT
$1,405,200±$124kHighest
283% above CT
Rentmedian gross, monthly
$3,501Highest
135% above CT
$2,025±$741Lowest
36% above CT
$2,509±$709
69% above CT
Property taxmedian, yearly
$10,000+Highest
at least 51% above CT
$8,843Lowest
33% above CT
$10,000+Highest
at least 51% above CT
Renters paying 30%+of income on rent
77.9%±36.6Highest
CT: 52.6%
44%±12.3Lowest
CT: 52.6%
51.8%±11
CT: 52.6%
Weston and Westport are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line
1.8%Lowest
CT: 10%
3.6%Highest
CT: 10%
3.2%
CT: 10%
Housing
Homeownersof occupied homes
96.9%Highest
CT: 66.5%
90.4%
CT: 66.5%
88.8%Lowest
CT: 66.5%
Typical home builtmedian year
1967Lowest
same as CT
1976Highest
9 yrs newer than CT
1967Lowest
same as CT
Getting to work
Average commuteone way
47 minHighest
76% above CT
30 minLowest
12% above CT
41 min
54% above CT
Work from home
44.9%±7.5Highest
CT: 16%
30.2%±5.3Lowest
CT: 16%
41.5%±3.6
CT: 16%
Weston and Westport 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 #5 of 149 in CT #7 of 149 in CT #3 of 149 in CT
School district Weston School District Madison School District Westport School District
High school in town Weston High School Daniel Hand High School Staples High School
Students per teacherat that high school
10.8Highest
9.8Lowest
10.7
On TownTapestry
Old photos in History None yet None yet None yet

CT 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.