| Index | Winter Park | Florida | National |
| Average Test Scores | 54% | 55% | 48% |
| Student/Teacher ratio | 15:1 | 17:1 | 16:1 |
| Total public schools | 8 | 3,388 | 79,221 |
| Total private schools | 16 | 1,640 | 24,874 |
| Total post-secondary schools | 7 | 466 | 7,963 |
| Index | Winter Park | Florida | National |
| Completed 8th grade | 93.9% | 84.0% | 84.3% |
| Completed high school | 93.5% | 83.0% | 83.0% |
| Completed some college | 80.3% | 58.0% | 59.4% |
| Completed associate degree | 66.3% | 37.4% | 38.5% |
| Completed bachelors | 59.5% | 27.9% | 30.3% |
| Completed masters | 27.6% | 10.0% | 11.5% |
| Completed professional degree | 11.5% | 3.1% | 3.3% |
| Completed doctorate | 3.2% | 1.1% | 1.3% |
There are a total of 8 public schools, 16 private schools and 7 post-secondary schools in Winter Park. Using the proficiency score averages, the average test scores for Winter Park, FL schools is 54%. The average student to teacher ratio is 15:1. In Winter Park, FL, an average of 93.9% of students have completed 8th grade and an average of 93.5% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Chuluota, FL | 1,939 | 78% | 61.5% |
| Oviedo, FL | 41,062 | 74% | 54.8% |
| Winter Springs, FL | 36,859 | 70% | 46.6% |
| Longwood, FL | 15,514 | 69% | 44.3% |
| Windermere, FL | 3,497 | 69% | 43.9% |
| Winter Park, FL | 30,764 | 54% | 12.8% |
| City | Population | Avg. Test Scores | National Avg. |
| Brooklyn Center, MN | 30,755 | 33% | 32.3% |
| Petersburg, VA | 30,791 | 53% | 10.8% |
| Cleburne, TX | 30,812 | 34% | 28.9% |
| Ithaca, NY | 30,715 | 57% | 18.3% |
| Algonquin, IL | 30,848 | 48% | 0.9% |
| Winter Park, FL | 30,764 | 54% | 12.8% |
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