| | Winchester, KY | Carlisle, KY | United States |
| Population | 18,993 | 2,648 | 329,725,481 |
| Female Population | 53.7% | 51.2% | 50.5% |
| Male Population | 46.3% | 48.8% | 49.5% |
| Median Age | 36.9 | 45.8 | 38.4 |
| space3 | | | |
| Population - 2010 | 18,364 | 2,085 | 309,327,143 |
| Population - 2000 | 16,724 | 1,917 | 285,036,114 |
| Population - 1990 | 15,799 | 1,639 | 251,960,433 |
| Pop. 2000 to Now | 11.6% | 7.4% | 15.6% |
| Pop. 1990 to Now | 18.1% | 25.6% | 30.8% |
| space4 | | | |
| Population Density | 2,077.8 | 1,995.5 | 93.4 |
| Land Area | 9.1 | 1.3 | 3,531,905.4 |
| Water Area | 0.1 | 0.0 | 264,836.8 |
| space | | | |
| Est. Total Population By Age | | | |
| | Winchester, KY | Carlisle, KY | United States |
| Age 0 to 4 | 7.1% | 2.6% | 5.9% |
| Age 5 to 9 | 6.3% | 6.7% | 6.1% |
| Age 10 to 14 | 6.5% | 7.3% | 6.6% |
| Age 15 to 17 | 3.7% | 3.0% | 3.9% |
| Age 18 to 20 | 3.7% | 3.4% | 4.0% |
| Age 21 to 24 | 5.4% | 4.9% | 5.2% |
| Age 25 to 34 | 15.1% | 11.5% | 13.8% |
| Age 35 to 44 | 10.8% | 10.2% | 12.9% |
| Age 45 to 54 | 14.6% | 14.3% | 12.6% |
| Age 55 to 59 | 5.5% | 9.4% | 6.7% |
| Age 60 to 64 | 4.9% | 6.1% | 6.3% |
| Age 65 to 74 | 9.0% | 11.6% | 9.6% |
| Age 75 to 84 | 4.8% | 5.1% | 4.5% |
| Age 85 and over | 2.8% | 4.0% | 1.9% |
| space1 | | | |
| Race | | | |
| | Winchester, KY | Carlisle, KY | United States |
| White | 84.7% | 92.9% | 59.4% |
| Black | 7.2% | 3.2% | 12.2% |
| Asian | 1.0% | 0.0% | 5.6% |
| Native American | 0.0% | 0.4% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 0.1% | 0.0% | 0.4% |
| Two or More Races | 2.3% | 3.5% | 3.2% |
| Hispanic | 4.6% | 0.0% | 18.4% |
| space2 | | | |
| Marriage & Family | | | |
| | Winchester, KY | Carlisle, KY | United States |
| Married Population | 45.1% | 39.7% | 49.8% |
| Currently Married | 42.3% | 36.3% | 48.0% |
| Married but Separated | 2.8% | 3.4% | 1.8% |
| Single Population | 54.9% | 60.3% | 50.2% |
| Never Married | 30.4% | 25.7% | 33.8% |
| Divorced | 17.5% | 22.7% | 10.8% |
| Widowed | 6.9% | 11.9% | 5.6% |
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| Household Size | 2.33 | 2.33 | 2.60 |
| Households | 8,031 | 1,098 | 124,010,992 |
| Family Households | 4,826 | 663 | 80,755,759 |
| Married couple, w/children | 25.6% | 29.3% | 30.5% |
| Married couple, no children | 36.8% | 32.4% | 42.9% |
| Non Family Households | 3,205 | 435 | 43,255,233 |
| Single householder, w/children | 29.8% | 19.3% | 15.8% |
| Single householder, no children | 7.8% | 19.0% | 10.8% |