| Index | Winchester | Massachusetts | National |
| Average Test Scores | 81% | 52% | 48% |
| Student/Teacher ratio | 14:1 | 14:1 | 16:1 |
| Total public schools | 7 | 1,167 | 79,221 |
| Total private schools | 4 | 508 | 24,874 |
| Total post-secondary schools | n/a | 193 | 7,963 |
| Index | Winchester | Massachusetts | National |
| Completed 8th grade | 97.1% | 88.3% | 84.3% |
| Completed high school | 96.8% | 87.2% | 83.0% |
| Completed some college | 86.8% | 65.0% | 59.4% |
| Completed associate degree | 79.0% | 49.0% | 38.5% |
| Completed bachelors | 74.3% | 41.2% | 30.3% |
| Completed masters | 43.4% | 18.2% | 11.5% |
| Completed professional degree | 15.5% | 5.4% | 3.3% |
| Completed doctorate | 6.4% | 2.6% | 1.3% |
There are a total of 7 public schools, 4 private schools and n/a post-secondary schools in Winchester. Using the proficiency score averages, the average test scores for Winchester, MA schools is 81%. The average student to teacher ratio is 14:1. In Winchester, MA, an average of 97.1% of students have completed 8th grade and an average of 96.8% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Dover, MA | 2,518 | 85% | 77.4% |
| Belmont, MA | 26,158 | 84% | 74.0% |
| West Concord, MA | 7,294 | 81% | 67.7% |
| Wellesley, MA | 28,747 | 80% | 66.0% |
| Lexington, MA | 33,304 | 78% | 63.1% |
| Winchester, MA | 22,760 | 81% | 69.3% |
| City | Population | Avg. Test Scores | National Avg. |
| Kihei, HI | 22,749 | 56% | 16.9% |
| Roselle, IL | 22,744 | 48% | 0.5% |
| Hastings, MN | 22,796 | 61% | 27.2% |
| Radcliff, KY | 22,796 | 33% | 31.9% |
| Griffin, GA | 22,724 | 29% | 39.1% |
| Winchester, MA | 22,760 | 81% | 69.3% |
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