| Index | Winter Garden | Florida | National |
| Average Test Scores | 64% | 55% | 48% |
| Student/Teacher ratio | 16:1 | 17:1 | 16:1 |
| Total public schools | 8 | 3,388 | 79,221 |
| Total private schools | 2 | 1,640 | 24,874 |
| Total post-secondary schools | 2 | 466 | 7,963 |
| Index | Winter Garden | Florida | National |
| Completed 8th grade | 87.4% | 84.0% | 84.3% |
| Completed high school | 87.0% | 83.0% | 83.0% |
| Completed some college | 63.8% | 58.0% | 59.4% |
| Completed associate degree | 46.6% | 37.4% | 38.5% |
| Completed bachelors | 37.1% | 27.9% | 30.3% |
| Completed masters | 13.9% | 10.0% | 11.5% |
| Completed professional degree | 3.4% | 3.1% | 3.3% |
| Completed doctorate | 0.6% | 1.1% | 1.3% |
There are a total of 8 public schools, 2 private schools and 2 post-secondary schools in Winter Garden. Using the proficiency score averages, the average test scores for Winter Garden, FL schools is 64%. The average student to teacher ratio is 16:1. In Winter Garden, FL, an average of 87.4% of students have completed 8th grade and an average of 87.0% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Oakland, FL | 3,065 | 71% | 46.9% |
| Windermere, FL | 3,497 | 69% | 43.9% |
| Minneola, FL | 12,223 | 69% | 43.0% |
| Maitland, FL | 17,749 | 65% | 34.9% |
| Clermont, FL | 36,757 | 64% | 34.2% |
| Winter Garden, FL | 44,888 | 64% | 32.5% |
| City | Population | Avg. Test Scores | National Avg. |
| Plainfield, IL | 44,857 | 44% | 9.3% |
| Danville, CA | 44,933 | 75% | 56.1% |
| Oakland Park, FL | 44,950 | 41% | 15.5% |
| Binghamton, NY | 44,819 | 43% | 10.5% |
| Farmington, NM | 44,967 | 36% | 25.3% |
| Winter Garden, FL | 44,888 | 64% | 32.5% |
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