| PEOPLE | Winchester | Bear | United States |
| Population | 26,203 | 19,371 | 308,035,306 |
| Pop. Density | 2,838 | 3,391 | 87 |
| Pop. Change | 13.19% | 8.69% | 8.07% |
| Median Age | 35.1 | 33.1 | 37.3 |
| Households | 10,607 | 6,907 | 116,716,292 |
| Household Size | 2.38 | 2.8 | 2.58 |
| Male Population | 49.22% | 48.30% | 49.27% |
| Female Population | 50.78% | 51.70% | 50.96% |
| Married Population | 35.58% | 46.23% | 47.02% |
| Single Population | 64.42% | 53.77% | 52.98% |
| ESTIMATED TOTAL POPULATION BY AGE | | | |
| Age 0 to 4 | 6.77% | 7.35% | 6.56% |
| Age 5 to 9 | 6.39% | 7.27% | 6.61% |
| Age 10 to 14 | 5.65% | 7.59% | 6.71% |
| Age 15 to 17 | 3.40% | 4.80% | 4.21% |
| Age 18 to 20 | 4.02% | 3.04% | 2.95% |
| Age 21 to 24 | 8.83% | 7.13% | 7.01% |
| Age 25 to 34 | 14.83% | 15.68% | 13.33% |
| Age 35 to 44 | 11.83% | 15.18% | 13.33% |
| Age 45 to 49 | 13.38% | 15.02% | 14.61% |
| Age 50 to 54 | 13.38% | 15.02% | 14.61% |
| Age 55 to 59 | 10.85% | 9.98% | 11.84% |
| Age 60 to 64 | 10.85% | 9.98% | 11.84% |
| Age 65 to 74 | 6.74% | 4.70% | 7.05% |
| Age 75 to 84 | 5.20% | 1.78% | 4.24% |
| Age 85 and over | 2.09% | 0.47% | 1.78% |
| RACE | | | |
| White | 74.54% | 50.47% | 72.41% |
| Black | 10.93% | 34.49% | 12.61% |
| Asian | 2.33% | 4.19% | 4.75% |
| American Indian | 0.35% | 0.32% | 0.95% |
| Other | 11.84% | 10.53% | 9.28% |
| Hispanic | 0.00% | 5.54% | 16.35% |
| Non-Hispanic | 100.00% | 94.46% | 83.65% |
| FAMILY | | | |
| Married, w/children | 27.09% | 30.64% | 30.42% |
| Married, no children | 41.06% | 33.26% | 42.46% |
| Single, w/children | 17.95% | 19.22% | 14.39% |
| Single, no children | 13.90% | 16.87% | 12.73% |
| Divorced | 15.26% | 13.42% | 10.62% |
| Separated | 9.90% | 3.28% | 4.97% |
| Widowed | 8.00% | 2.82% | 6.14% |
| Now Married | 36.21% | 46.76% | 46.32% |
| Never Married | 30.62% | 33.72% | 31.95% |