| | Winter Park, FL | Orlando, FL | United States |
| Population | 29,672 | 302,968 | 329,725,481 |
| Female Population | 52.7% | 51.5% | 50.5% |
| Male Population | 47.3% | 48.5% | 49.5% |
| Median Age | 45.3 | 34.4 | 38.4 |
| space3 | | | |
| Population - 2010 | 27,805 | 239,219 | 309,327,143 |
| Population - 2000 | 24,090 | 185,951 | 285,036,114 |
| Population - 1990 | 22,242 | 164,693 | 251,960,433 |
| Pop. 2000 to Now | 27.3% | 55.7% | 15.6% |
| Pop. 1990 to Now | 37.9% | 75.8% | 30.8% |
| space4 | | | |
| Population Density | 3,393.0 | 2,751.2 | 93.4 |
| Land Area | 8.7 | 110.1 | 3,531,905.4 |
| Water Area | 1.5 | 8.7 | 264,836.8 |
| space | | | |
| Est. Total Population By Age | | | |
| | Winter Park, FL | Orlando, FL | United States |
| Age 0 to 4 | 4.0% | 6.7% | 5.9% |
| Age 5 to 9 | 3.8% | 5.8% | 6.1% |
| Age 10 to 14 | 5.4% | 5.3% | 6.6% |
| Age 15 to 17 | 4.1% | 3.4% | 3.9% |
| Age 18 to 20 | 5.4% | 2.5% | 4.0% |
| Age 21 to 24 | 5.0% | 5.5% | 5.2% |
| Age 25 to 34 | 11.5% | 22.0% | 13.8% |
| Age 35 to 44 | 10.4% | 16.0% | 12.9% |
| Age 45 to 54 | 13.2% | 12.0% | 12.6% |
| Age 55 to 59 | 7.2% | 5.7% | 6.7% |
| Age 60 to 64 | 7.5% | 4.6% | 6.3% |
| Age 65 to 74 | 11.2% | 6.6% | 9.6% |
| Age 75 to 84 | 7.4% | 2.8% | 4.5% |
| Age 85 and over | 4.0% | 1.1% | 1.9% |
| space1 | | | |
| Race | | | |
| | Winter Park, FL | Orlando, FL | United States |
| White | 73.6% | 35.0% | 59.4% |
| Black | 5.1% | 22.5% | 12.2% |
| Asian | 5.5% | 3.9% | 5.6% |
| Native American | 0.1% | 0.1% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 0.2% | 0.9% | 0.4% |
| Two or More Races | 2.8% | 3.5% | 3.2% |
| Hispanic | 12.7% | 34.2% | 18.4% |
| space2 | | | |
| Marriage & Family | | | |
| | Winter Park, FL | Orlando, FL | United States |
| Married Population | 45.5% | 40.2% | 49.8% |
| Currently Married | 44.4% | 37.8% | 48.0% |
| Married but Separated | 1.1% | 2.4% | 1.8% |
| Single Population | 54.5% | 59.8% | 50.2% |
| Never Married | 33.9% | 43.2% | 33.8% |
| Divorced | 13.1% | 12.7% | 10.8% |
| Widowed | 7.5% | 3.9% | 5.6% |
| space5 | | | |
| Household Size | 2.25 | 2.53 | 2.60 |
| Households | 12,462 | 118,834 | 124,010,992 |
| Family Households | 6,797 | 65,783 | 80,755,759 |
| Married couple, w/children | 28.0% | 29.9% | 30.5% |
| Married couple, no children | 50.5% | 34.0% | 42.9% |
| Non Family Households | 5,665 | 53,051 | 43,255,233 |
| Single householder, w/children | 10.3% | 20.8% | 15.8% |
| Single householder, no children | 11.3% | 15.3% | 10.8% |