| Index | Winchester | New Hampshire | National |
| Average Test Scores | 27% | 52% | 48% |
| Student/Teacher ratio | 12:1 | 13:1 | 16:1 |
| Total public schools | 3 | 234 | 79,221 |
| Total private schools | n/a | 144 | 24,874 |
| Total post-secondary schools | n/a | 40 | 7,963 |
| Index | Winchester | New Hampshire | National |
| Completed 8th grade | 77.3% | 89.5% | 84.3% |
| Completed high school | 75.5% | 88.4% | 83.0% |
| Completed some college | 36.9% | 64.2% | 59.4% |
| Completed associate degree | 23.6% | 45.3% | 38.5% |
| Completed bachelors | 11.0% | 35.5% | 30.3% |
| Completed masters | 3.6% | 13.4% | 11.5% |
| Completed professional degree | 0.7% | 3.3% | 3.3% |
| Completed doctorate | 0.0% | 1.4% | 1.3% |
There are a total of 3 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, NH schools is 27%. The average student to teacher ratio is 12:1. In Winchester, NH, an average of 77.3% of students have completed 8th grade and an average of 75.5% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Northfield, MA | 970 | 55% | 13.5% |
| Keene, NH | 22,823 | 46% | 4.2% |
| Troy, NH | 857 | 45% | 7.3% |
| West Swanzey, NH | 1,180 | 45% | 7.3% |
| Hinsdale, NH | 1,470 | 38% | 20.8% |
| Winchester, NH | 1,939 | 27% | 44.8% |
| City | Population | Avg. Test Scores | National Avg. |
| Fennville, MI | 1,939 | 29% | 38.8% |
| Blooming Prairie, MN | 1,939 | 61% | 27.6% |
| Farmington, IL | 1,939 | 32% | 33.3% |
| Chuluota, FL | 1,939 | 78% | 61.5% |
| Westernport, MD | 1,938 | 40% | 17.7% |
| Winchester, NH | 1,939 | 27% | 44.8% |
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