| | Wintergreen, VA | Winchester, VA | United States |
| Population | 456 | 28,194 | 329,725,481 |
| Female Population | 38.4% | 51.1% | 50.5% |
| Male Population | 61.6% | 48.9% | 49.5% |
| Median Age | 73.2 | 36.6 | 38.4 |
| space3 | | | |
| Population - 2010 | 125 | 26,150 | 309,327,143 |
| Population - 2000 | 452 | 23,585 | 285,036,114 |
| Population - 1990 | 338 | 21,947 | 251,960,433 |
| Pop. 2000 to Now | 13.5% | 17.5% | 15.6% |
| Pop. 1990 to Now | 51.8% | 26.2% | 30.8% |
| space4 | | | |
| Population Density | 51.8 | 3,066.9 | 93.4 |
| Land Area | 8.8 | 9.2 | 3,531,905.4 |
| Water Area | 0.0 | 0.0 | 264,836.8 |
| space | | | |
| Est. Total Population By Age | | | |
| | Wintergreen, VA | Winchester, VA | United States |
| Age 0 to 4 | 0.0% | 6.1% | 5.9% |
| Age 5 to 9 | 0.0% | 6.4% | 6.1% |
| Age 10 to 14 | 0.0% | 6.2% | 6.6% |
| Age 15 to 17 | 0.0% | 4.1% | 3.9% |
| Age 18 to 20 | 0.0% | 5.7% | 4.0% |
| Age 21 to 24 | 2.2% | 4.7% | 5.2% |
| Age 25 to 34 | 1.1% | 13.8% | 13.8% |
| Age 35 to 44 | 0.0% | 12.3% | 12.9% |
| Age 45 to 54 | 21.3% | 12.3% | 12.6% |
| Age 55 to 59 | 0.0% | 6.4% | 6.7% |
| Age 60 to 64 | 0.2% | 5.6% | 6.3% |
| Age 65 to 74 | 33.3% | 9.4% | 9.6% |
| Age 75 to 84 | 26.5% | 5.1% | 4.5% |
| Age 85 and over | 15.4% | 1.7% | 1.9% |
| space1 | | | |
| Race | | | |
| | Wintergreen, VA | Winchester, VA | United States |
| White | 76.3% | 64.5% | 59.4% |
| Black | 21.9% | 9.5% | 12.2% |
| Asian | 1.8% | 2.1% | 5.6% |
| Native American | 0.0% | 0.2% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 0.0% | 0.9% | 0.4% |
| Two or More Races | 0.0% | 4.7% | 3.2% |
| Hispanic | 0.0% | 18.2% | 18.4% |
| space2 | | | |
| Marriage & Family | | | |
| | Wintergreen, VA | Winchester, VA | United States |
| Married Population | 80.5% | 42.9% | 49.8% |
| Currently Married | 80.3% | 40.5% | 48.0% |
| Married but Separated | 0.2% | 2.4% | 1.8% |
| Single Population | 19.5% | 57.1% | 50.2% |
| Never Married | 3.9% | 37.7% | 33.8% |
| Divorced | 15.6% | 13.7% | 10.8% |
| Widowed | 0.0% | 5.7% | 5.6% |
| space5 | | | |
| Household Size | 1.71 | 2.47 | 2.60 |
| Households | 255 | 11,018 | 124,010,992 |
| Family Households | 184 | 6,026 | 80,755,759 |
| Married couple, w/children | 0.0% | 26.2% | 30.5% |
| Married couple, no children | 100.0% | 40.8% | 42.9% |
| Non Family Households | 71 | 4,992 | 43,255,233 |
| Single householder, w/children | 0.0% | 22.2% | 15.8% |
| Single householder, no children | 0.0% | 10.9% | 10.8% |