| Index | Winchester | Tennessee | National |
| Average Test Scores | 32% | 35% | 48% |
| Student/Teacher ratio | n/a | n/a | 16:1 |
| Total public schools | 5 | 1,390 | 79,221 |
| Total private schools | n/a | 430 | 24,874 |
| Total post-secondary schools | n/a | 189 | 7,963 |
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| Index | Winchester | Tennessee | National |
| Completed 8th grade | 81.3% | 82.0% | 84.3% |
| Completed high school | 79.3% | 79.9% | 83.0% |
| Completed some college | 53.8% | 53.2% | 59.4% |
| Completed associate degree | 32.3% | 32.2% | 38.5% |
| Completed bachelors | 22.2% | 25.4% | 30.3% |
| Completed masters | 7.7% | 9.3% | 11.5% |
| Completed professional degree | 1.7% | 2.8% | 3.3% |
| Completed doctorate | 0.3% | 1.2% | 1.3% |
There are a total of 5 public schools, n/a private schools and n/a post-secondary schools in Winchester. Using the proficiency score averages, the average test scores for Winchester, TN schools is 32%. The average student to teacher ratio is n/a. In Winchester, TN, an average of 81.3% of students have completed 8th grade and an average of 79.3% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Sewanee, TN | 2,625 | 57% | 18.8% |
| Hillsboro, TN | 338 | 45% | 7.3% |
| Lynchburg, Moore County, TN | 6,396 | 34% | 28.6% |
| Estill Springs, TN | 2,063 | 32% | 33.3% |
| Tullahoma, TN | 19,982 | 30% | 37.6% |
| Winchester, TN | 8,818 | 32% | 34.1% |
| City | Population | Avg. Test Scores | National Avg. |
| Fort Valley, GA | 8,817 | 23% | 52.4% |
| Canonsburg, PA | 8,815 | 74% | 53.5% |
| Andover, MA | 8,821 | 68% | 42.2% |
| Scott, LA | 8,815 | 74% | 54.9% |
| Oxford, NC | 8,812 | 28% | 42.5% |
| Winchester, TN | 8,818 | 32% | 34.1% |
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