| | Winchester, CT | Monroe, CT | United States |
| Population | 10,335 | 18,927 | 329,725,481 |
| Female Population | 48.8% | 48.7% | 50.5% |
| Male Population | 51.2% | 51.3% | 49.5% |
| Median Age | 50.7 | 41.4 | 38.4 |
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| Population - 2010 | 11,240 | 19,502 | 309,327,143 |
| Population - 2000 | 10,664 | 19,247 | 285,036,114 |
| Population - 1990 | 11,524 | 16,896 | 251,960,433 |
| Pop. 2000 to Now | -1.1% | 0.4% | 15.6% |
| Pop. 1990 to Now | -8.5% | 14.4% | 30.8% |
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| Population Density | 317.9 | 725.9 | 93.4 |
| Land Area | 32.5 | 26.1 | 3,531,905.4 |
| Water Area | 1.3 | 0.2 | 264,836.8 |
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| Est. Total Population By Age | | | |
| | Winchester, CT | Monroe, CT | United States |
| Age 0 to 4 | 3.1% | 7.7% | 5.9% |
| Age 5 to 9 | 5.5% | 4.9% | 6.1% |
| Age 10 to 14 | 3.0% | 8.3% | 6.6% |
| Age 15 to 17 | 2.1% | 4.9% | 3.9% |
| Age 18 to 20 | 2.6% | 2.7% | 4.0% |
| Age 21 to 24 | 3.6% | 5.8% | 5.2% |
| Age 25 to 34 | 11.5% | 7.5% | 13.8% |
| Age 35 to 44 | 13.7% | 12.0% | 12.9% |
| Age 45 to 54 | 9.9% | 15.5% | 12.6% |
| Age 55 to 59 | 7.7% | 9.4% | 6.7% |
| Age 60 to 64 | 11.7% | 6.6% | 6.3% |
| Age 65 to 74 | 14.4% | 8.7% | 9.6% |
| Age 75 to 84 | 4.3% | 4.5% | 4.5% |
| Age 85 and over | 6.8% | 1.7% | 1.9% |
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| Race | | | |
| | Winchester, CT | Monroe, CT | United States |
| White | 91.3% | 78.8% | 59.4% |
| Black | 1.1% | 3.4% | 12.2% |
| Asian | 0.0% | 5.4% | 5.6% |
| Native American | 0.3% | 0.0% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 0.0% | 0.0% | 0.4% |
| Two or More Races | 2.0% | 3.7% | 3.2% |
| Hispanic | 5.2% | 8.8% | 18.4% |
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| Marriage & Family | | | |
| | Winchester, CT | Monroe, CT | United States |
| Married Population | 48.0% | 62.1% | 49.8% |
| Currently Married | 46.4% | 61.6% | 48.0% |
| Married but Separated | 1.6% | 0.4% | 1.8% |
| Single Population | 52.0% | 37.9% | 50.2% |
| Never Married | 33.0% | 25.2% | 33.8% |
| Divorced | 14.7% | 9.0% | 10.8% |
| Widowed | 4.3% | 3.8% | 5.6% |
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| Household Size | 2.18 | 3.01 | 2.60 |
| Households | 4,714 | 6,274 | 124,010,992 |
| Family Households | 2,600 | 4,956 | 80,755,759 |
| Married couple, w/children | 20.7% | 42.9% | 30.5% |
| Married couple, no children | 60.4% | 45.7% | 42.9% |
| Non Family Households | 2,114 | 1,318 | 43,255,233 |
| Single householder, w/children | 11.0% | 4.1% | 15.8% |
| Single householder, no children | 7.8% | 7.2% | 10.8% |