| Index | Winchester | Virginia | National |
| Average Test Scores | 74% | 79% | 48% |
| Student/Teacher ratio | 13:1 | 13:1 | 16:1 |
| Total public schools | 19 | 1,596 | 79,221 |
| Total private schools | 6 | 553 | 24,874 |
| Total post-secondary schools | 2 | 199 | 7,963 |
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| Index | Winchester | Virginia | National |
| Completed 8th grade | 80.0% | 85.9% | 84.3% |
| Completed high school | 78.1% | 84.7% | 83.0% |
| Completed some college | 55.5% | 64.1% | 59.4% |
| Completed associate degree | 38.9% | 44.2% | 38.5% |
| Completed bachelors | 31.3% | 36.9% | 30.3% |
| Completed masters | 13.5% | 15.7% | 11.5% |
| Completed professional degree | 5.3% | 4.2% | 3.3% |
| Completed doctorate | 1.6% | 1.7% | 1.3% |
There are a total of 19 public schools, 6 private schools and 2 post-secondary schools in Winchester. Using the proficiency score averages, the average test scores for Winchester, VA schools is 74%. The average student to teacher ratio is 13:1. In Winchester, VA, an average of 80.0% of students have completed 8th grade and an average of 78.1% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Middletown, VA | 1,621 | 83% | 72.9% |
| Stephens City, VA | 2,334 | 80% | 66.0% |
| Berryville, VA | 4,475 | 77% | 61.1% |
| Strasburg, VA | 6,883 | 77% | 59.4% |
| Boyce, VA | 887 | 72% | 50.0% |
| Winchester, VA | 28,825 | 74% | 54.4% |
| City | Population | Avg. Test Scores | National Avg. |
| Enterprise, AL | 28,827 | 58% | 20.4% |
| Glen Ellyn, IL | 28,828 | 59% | 23.0% |
| Burlington, MA | 28,820 | 62% | 29.9% |
| Saratoga Springs, NY | 28,832 | 73% | 52.5% |
| East Chicago, IN | 28,835 | 22% | 54.4% |
| Winchester, VA | 28,825 | 74% | 54.4% |
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