| | Winchester, MA | Highlands, NC | United States |
| Population | 22,875 | 1,105 | 329,725,481 |
| Female Population | 53.6% | 53.2% | 50.5% |
| Male Population | 46.4% | 46.8% | 49.5% |
| Median Age | 42.4 | 60.2 | 38.4 |
| space3 | | | |
| Population - 2010 | 21,473 | 931 | 309,327,143 |
| Population - 2000 | 20,810 | 909 | 285,036,114 |
| Population - 1990 | 20,267 | 948 | 251,960,433 |
| Pop. 2000 to Now | 9.0% | 8.3% | 15.6% |
| Pop. 1990 to Now | 11.9% | 3.8% | 30.8% |
| space4 | | | |
| Population Density | 3,792.9 | 180.4 | 93.4 |
| Land Area | 6.0 | 6.1 | 3,531,905.4 |
| Water Area | 0.3 | 0.1 | 264,836.8 |
| space | | | |
| Est. Total Population By Age | | | |
| | Winchester, MA | Highlands, NC | United States |
| Age 0 to 4 | 5.7% | 0.0% | 5.9% |
| Age 5 to 9 | 8.0% | 0.7% | 6.1% |
| Age 10 to 14 | 8.8% | 1.8% | 6.6% |
| Age 15 to 17 | 5.2% | 3.2% | 3.9% |
| Age 18 to 20 | 2.6% | 4.1% | 4.0% |
| Age 21 to 24 | 2.4% | 6.2% | 5.2% |
| Age 25 to 34 | 6.8% | 5.4% | 13.8% |
| Age 35 to 44 | 13.8% | 9.2% | 12.9% |
| Age 45 to 54 | 17.6% | 8.1% | 12.6% |
| Age 55 to 59 | 7.2% | 10.2% | 6.7% |
| Age 60 to 64 | 4.3% | 14.3% | 6.3% |
| Age 65 to 74 | 8.4% | 21.6% | 9.6% |
| Age 75 to 84 | 5.6% | 13.6% | 4.5% |
| Age 85 and over | 3.6% | 1.4% | 1.9% |
| space1 | | | |
| Race | | | |
| | Winchester, MA | Highlands, NC | United States |
| White | 75.4% | 89.4% | 59.4% |
| Black | 1.8% | 3.3% | 12.2% |
| Asian | 15.2% | 0.7% | 5.6% |
| Native American | 0.3% | 0.0% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 1.6% | 0.0% | 0.4% |
| Two or More Races | 3.6% | 0.8% | 3.2% |
| Hispanic | 2.1% | 5.8% | 18.4% |
| space2 | | | |
| Marriage & Family | | | |
| | Winchester, MA | Highlands, NC | United States |
| Married Population | 62.2% | 48.4% | 49.8% |
| Currently Married | 61.7% | 47.2% | 48.0% |
| Married but Separated | 0.6% | 1.2% | 1.8% |
| Single Population | 37.8% | 51.6% | 50.2% |
| Never Married | 24.1% | 28.0% | 33.8% |
| Divorced | 7.5% | 17.9% | 10.8% |
| Widowed | 6.2% | 5.7% | 5.6% |
| space5 | | | |
| Household Size | 2.77 | 1.56 | 2.60 |
| Households | 8,149 | 689 | 124,010,992 |
| Family Households | 5,980 | 289 | 80,755,759 |
| Married couple, w/children | 48.3% | 13.5% | 30.5% |
| Married couple, no children | 37.7% | 69.9% | 42.9% |
| Non Family Households | 2,169 | 400 | 43,255,233 |
| Single householder, w/children | 8.2% | 12.5% | 15.8% |
| Single householder, no children | 5.7% | 4.2% | 10.8% |