| 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 |
| 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 | 1,585 | 83% | 72.9% |
| Stephens City, VA | 2,254 | 80% | 66.0% |
| Berryville, VA | 4,338 | 77% | 61.1% |
| Strasburg, VA | 6,643 | 77% | 59.4% |
| Boyce, VA | 867 | 72% | 50.0% |
| Winchester, VA | 27,912 | 74% | 54.4% |
| City | Population | Avg. Test Scores | National Avg. |
| Oakdale, MN | 27,925 | 58% | 20.7% |
| Drexel Hill, PA | 27,925 | 44% | 8.9% |
| Jeffersontown, KY | 27,933 | 35% | 27.6% |
| Big Spring, TX | 27,878 | 31% | 35.4% |
| Lafayette, CO | 27,952 | 47% | 2.0% |
| Winchester, VA | 27,912 | 74% | 54.4% |
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