Compare towns
Windsor vs Chester vs New Milford
Cost, people, housing, commute and schools, side by side, each benchmarked against Connecticut.
What stands out worked out from the figures below
Windsor has the shortest commute (21 min average).
Chester has the oldest population (median age 54).
New Milford has the most kids (21.4% 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.
| Measure | Windsor | Chester | New Milford |
|---|---|---|---|
| Your priorities | |||
| People | |||
| Population | 29,468Highest |
3,825Lowest |
28,334 |
| Median age | 43.7±1.9 6% above CT |
54±3.4Highest 31% above CT |
42.1±1.9Lowest about the CT average |
| Kids under 18 | 19.2%±2.1 CT: 20.2% |
17.5%±4.9Lowest CT: 20.2% |
21.4%±2.6Highest CT: 20.2% |
| New Milford and Windsor are within the Census margin of error here, so we can’t say which is really higher. | |||
| Age 65+ | 20%±2 CT: 18.5% |
26.8%±4Highest CT: 18.5% |
17.7%±1.7Lowest CT: 18.5% |
| Bachelor’s degree+adults 25+ | 43.2% CT: 42.5% |
47.9%Highest CT: 42.5% |
41.2%Lowest CT: 42.5% |
| Enrolled in collegeshare of residents | 5.9%±1.3Highest CT: 7.1% |
4%±2.9Lowest CT: 7.1% |
5.1%±1.7 CT: 7.1% |
| Windsor and New Milford are within the Census margin of error here, so we can’t say which is really higher. | |||
| Cost of living | |||
| Household incomemedian | $104,725±$8kLowest 9% above CT |
$109,191±$18kHighest 14% above CT |
$106,411±$8k 11% above CT |
| Chester and New Milford are within the Census margin of error here, so we can’t say which is really higher. | |||
| Home valuemedian, owner-occupied | $305,200±$11kLowest 17% below CT |
$442,200±$25kHighest 21% above CT |
$391,500±$10k 7% above CT |
| Rentmedian gross, monthly | $1,681±$62Highest 13% above CT |
$1,549±$247Lowest 4% above CT |
$1,609±$152 8% above CT |
| Windsor and New Milford are within the Census margin of error here, so we can’t say which is really higher. | |||
| Property taxmedian, yearly | $5,351Lowest 19% below CT |
$6,364Highest 4% below CT |
$6,150 7% below CT |
| Renters paying 30%+of income on rent | 44.9%±10.9Lowest CT: 52.6% |
57.4%±22.1 CT: 52.6% |
57.7%±13.3Highest CT: 52.6% |
| New Milford and Chester are within the Census margin of error here, so we can’t say which is really higher. | |||
| Below poverty line | 6.7%Lowest CT: 10% |
11.8%Highest CT: 10% |
7.1% CT: 10% |
| Housing | |||
| Homeownersof occupied homes | 82.4%Highest CT: 66.5% |
73.2%Lowest CT: 66.5% |
80.4% CT: 66.5% |
| Typical home builtmedian year | 1970 3 yrs newer than CT |
1969Lowest 2 yrs newer than CT |
1975Highest 8 yrs newer than CT |
| Getting to work | |||
| Average commuteone way | 21 minLowest 19% below CT |
28 min 7% above CT |
30 minHighest 14% above CT |
| Work from home | 16.1%±3.2 CT: 16% |
18.3%±5.6Highest CT: 16% |
15.1%±2.5Lowest CT: 16% |
| Chester 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 | #117 of 149 in CT | #8 of 149 in CT | #110 of 149 in CT |
| School district | Capitol Region Education Council · Windsor School District | Chester School District | New Milford School District |
| High school in town | Windsor High School | None in town | New Milford High School |
| Students per teacherat that high school | 10.2Lowest |
— | 11.7Highest |
| 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.