| Index | Chestertown | New York | National |
| Average Test Scores | 46% | 56% | 48% |
| Student/Teacher ratio | n/a | n/a | 16:1 |
| Total public schools | n/a | 4,060 | 79,221 |
| Total private schools | n/a | 1,092 | 24,874 |
| Total post-secondary schools | n/a | 483 | 7,963 |
| Index | Chestertown | New York | National |
| Completed 8th grade | 88.9% | 83.5% | 84.3% |
| Completed high school | 88.9% | 82.1% | 83.0% |
| Completed some college | 35.4% | 59.5% | 59.4% |
| Completed associate degree | 14.2% | 43.4% | 38.5% |
| Completed bachelors | 11.4% | 34.7% | 30.3% |
| Completed masters | 8.6% | 15.1% | 11.5% |
| Completed professional degree | 0.0% | 4.2% | 3.3% |
| Completed doctorate | 0.0% | 1.5% | 1.3% |
There are a total of n/a public schools, n/a private schools and n/a post-secondary schools in Chestertown. Using the proficiency score averages, the average test scores for Chestertown, NY schools is 46%. The average student to teacher ratio is n/a. In Chestertown, NY, an average of 88.9% of students have completed 8th grade and an average of 88.9% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Bolton Landing, NY | 418 | 80% | 65.6% |
| Lake George, NY | 953 | 71% | 47.4% |
| North Creek, NY | 691 | 52% | 8.3% |
| Schroon Lake, NY | 888 | 52% | 8.3% |
| Warrensburg, NY | 3,209 | 48% | 0.5% |
| Chestertown, NY | 707 | 46% | 5.2% |
| City | Population | Avg. Test Scores | National Avg. |
| Howe, IN | 707 | 35% | 28.1% |
| Cliffside, NC | 707 | 52% | 8.3% |
| Margaretville, NY | 707 | 32% | 33.3% |
| Oxford, IA | 707 | 77% | 60.4% |
| Lake Village, IN | 707 | 55% | 13.5% |
| Chestertown, NY | 707 | 46% | 5.2% |
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