| Index | Winchester | Kentucky | National |
| Average Test Scores | 53% | 48% | 48% |
| Student/Teacher ratio | 15:1 | 16:1 | 16:1 |
| Total public schools | 13 | 1,157 | 79,221 |
| Total private schools | 4 | 298 | 24,874 |
| Total post-secondary schools | 1 | 130 | 7,963 |
| Index | Winchester | Kentucky | National |
| Completed 8th grade | 80.0% | 81.0% | 84.3% |
| Completed high school | 75.6% | 77.8% | 83.0% |
| Completed some college | 45.4% | 51.3% | 59.4% |
| Completed associate degree | 25.1% | 30.5% | 38.5% |
| Completed bachelors | 18.6% | 22.7% | 30.3% |
| Completed masters | 5.0% | 9.3% | 11.5% |
| Completed professional degree | 1.4% | 2.6% | 3.3% |
| Completed doctorate | 0.7% | 0.9% | 1.3% |
There are a total of 13 public schools, 4 private schools and 1 post-secondary schools in Winchester. Using the proficiency score averages, the average test scores for Winchester, KY schools is 53%. The average student to teacher ratio is 15:1. In Winchester, KY, an average of 80.0% of students have completed 8th grade and an average of 75.6% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Mount Sterling, KY | 7,404 | 48% | = 100 |
| North Middletown, KY | 749 | 47% | 2.1% |
| Paris, KY | 10,056 | 40% | 16.7% |
| Clay City, KY | 1,008 | 38% | 21.9% |
| Winchester, KY | 18,950 | 53% | 10.7% |
| City | Population | Avg. Test Scores | National Avg. |
| Milledgeville, GA | 18,956 | 24% | 50.0% |
| Laurel, MS | 18,971 | 40% | 17.4% |
| Orange, TX | 18,926 | 39% | 19.6% |
| Brownwood, TX | 18,977 | 32% | 33.9% |
| Menasha, WI | 18,920 | 36% | 25.1% |
| Winchester, KY | 18,950 | 53% | 10.7% |
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