What stands out worked out from the figures below

Westport has the most affordable homes ($1405k median).

Darien has the most expensive homes ($1822k 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.

Raising kidsAffordabilityOwning a homeShort commuteWorking from homeYounger crowdSettled, older crowdGrowing town

Measure	Westport	Darien
People
Population	27,528Highest	21,936Lowest
Median age	45.4±1.5Highest 10% above CT	40±1.5Lowest about the CT average
Kids under 18	27.9%±2.7Lowest CT: 20.2%	30.9%±2.4Highest CT: 20.2%
	Darien and Westport are within the Census margin of error here, so we can’t say which is really higher.
Age 65+	18.5%±1.8Highest CT: 18.5%	13.7%±2.1Lowest CT: 18.5%
Bachelor’s degree+adults 25+	79.9%Lowest CT: 42.5%	85.9%Highest CT: 42.5%
Enrolled in collegeshare of residents	3.2%±0.8Lowest CT: 7.1%	4.5%±1.4Highest CT: 7.1%
	Darien and Westport are within the Census margin of error here, so we can’t say which is really higher.
Cost of living
Household incomemedian	$250,001 161% above CT	$250,001 161% above CT
Home valuemedian, owner-occupied	$1,405,200±$124kLowest 283% above CT	$1,822,400±$171kHighest 397% above CT
Rentmedian gross, monthly	$2,509±$709Lowest 69% above CT	$3,501Highest 135% above CT
Property taxmedian, yearly	$10,000+ at least 51% above CT	$10,000+ at least 51% above CT
Renters paying 30%+of income on rent	51.8%±11Lowest CT: 52.6%	60.8%±11.7Highest CT: 52.6%
	Darien and Westport are within the Census margin of error here, so we can’t say which is really higher.
Below poverty line	3.2%Lowest CT: 10%	5.8%Highest CT: 10%
Housing
Homeownersof occupied homes	88.8%Highest CT: 66.5%	82.4%Lowest CT: 66.5%
Typical home builtmedian year	1967Highest same as CT	1956Lowest 11 yrs older than CT
Getting to work
Average commuteone way	41 minHighest 54% above CT	39 minLowest 46% above CT
Work from home	41.5%±3.6Highest CT: 16%	35.5%±6.6Lowest CT: 16%
	Westport and Darien 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	#3 of 149 in CT	#2 of 149 in CT
School district	Westport School District	Darien School District
High school in town	Staples High School	Darien High School
Students per teacherat that high school	10.7	10.7
On TownTapestry
Old photos in History	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.