| Index | Chester | New York | National |
| Average Test Scores | 48% | 56% | 48% |
| Student/Teacher ratio | n/a | n/a | 16:1 |
| Total public schools | 2 | 4,060 | 79,221 |
| Total private schools | n/a | 1,092 | 24,874 |
| Total post-secondary schools | n/a | 483 | 7,963 |
| Index | Chester | New York | National |
| Completed 8th grade | 89.6% | 83.5% | 84.3% |
| Completed high school | 89.6% | 82.1% | 83.0% |
| Completed some college | 65.6% | 59.5% | 59.4% |
| Completed associate degree | 38.6% | 43.4% | 38.5% |
| Completed bachelors | 27.3% | 34.7% | 30.3% |
| Completed masters | 8.6% | 15.1% | 11.5% |
| Completed professional degree | 2.5% | 4.2% | 3.3% |
| Completed doctorate | 1.5% | 1.5% | 1.3% |
There are a total of 2 public schools, n/a private schools and n/a post-secondary schools in Chester. Using the proficiency score averages, the average test scores for Chester, NY schools is 48%. The average student to teacher ratio is n/a. In Chester, NY, an average of 89.6% of students have completed 8th grade and an average of 89.6% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Firthcliffe, NY | 5,051 | 77% | 60.4% |
| Greenwood Lake, NY | 3,080 | 75% | 56.3% |
| Woodbury, NY | 10,700 | 72% | 49.7% |
| Warwick, NY | 6,769 | 71% | 47.9% |
| New City, NY | 34,060 | 68% | 42.6% |
| Chester, NY | 4,057 | 48% | 0.5% |
| City | Population | Avg. Test Scores | National Avg. |
| Bellaire, OH | 4,057 | 63% | 31.3% |
| Newcomerstown, OH | 4,058 | 54% | 12.5% |
| Livingston, TN | 4,058 | 30% | 37.5% |
| Forty Fort, PA | 4,055 | 52% | 7.3% |
| Clearwater, SC | 4,060 | 46% | 4.2% |
| Chester, NY | 4,057 | 48% | 0.5% |
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