| Index | Leonardtown | Maryland | National |
| Average Test Scores | 60% | 40% | 48% |
| Student/Teacher ratio | 15:1 | 16:1 | 16:1 |
| Total public schools | 7 | 1,163 | 79,221 |
| Total private schools | 6 | 674 | 24,874 |
| Total post-secondary schools | n/a | 112 | 7,963 |
| Index | Leonardtown | Maryland | National |
| Completed 8th grade | 87.4% | 87.5% | 84.3% |
| Completed high school | 85.9% | 86.5% | 83.0% |
| Completed some college | 58.0% | 64.2% | 59.4% |
| Completed associate degree | 37.8% | 44.8% | 38.5% |
| Completed bachelors | 35.5% | 38.4% | 30.3% |
| Completed masters | 18.5% | 17.7% | 11.5% |
| Completed professional degree | 2.3% | 5.5% | 3.3% |
| Completed doctorate | 1.1% | 2.5% | 1.3% |
There are a total of 7 public schools, 6 private schools and n/a post-secondary schools in Leonardtown. Using the proficiency score averages, the average test scores for Leonardtown, MD schools is 60%. The average student to teacher ratio is 15:1. In Leonardtown, MD, an average of 87.4% of students have completed 8th grade and an average of 85.9% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Montross, VA | 553 | 76% | 58.9% |
| Mechanicsville, MD | 1,724 | 55% | 15.0% |
| Tall Timbers, MD | 570 | 50% | 4.2% |
| California, MD | 14,730 | 49% | 2.1% |
| Lexington Park, MD | 12,934 | 46% | 3.5% |
| Leonardtown, MD | 3,795 | 60% | 24.0% |
| City | Population | Avg. Test Scores | National Avg. |
| North Wildwood, NJ | 3,794 | 52% | 8.3% |
| Carter Lake, IA | 3,799 | 52% | 8.3% |
| Plainwell, MI | 3,799 | 48% | 0.2% |
| Sewickley, PA | 3,800 | 81% | 67.7% |
| Brookville, PA | 3,801 | 55% | 14.6% |
| Leonardtown, MD | 3,795 | 60% | 24.0% |
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