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For the 2025-26 school year, there are 7 public schools serving 4,146 students in Cheshire, CT (there are , serving 747 private students). 85% of all K-12 students in Cheshire, CT are educated in public schools (compared to the CT state average of 88%). Cheshire has one of the highest concentrations of top-ranked public schools in Connecticut.

The top-ranked public schools in Cheshire, CT are Norton School, Highland School and Chapman School. Overall testing rank is based on a school's combined math and reading proficiency test score ranking.

Cheshire, CT public schools have an average math proficiency score of 71% (versus the Connecticut public school average of 42%), and reading proficiency score of 75% (versus the 51% statewide average). Schools in Cheshire have an average ranking of 9/10, which is in the top 20% of Connecticut public schools.

Minority enrollment is 26% of the student body (majority Hispanic and Asian), which is less than the Connecticut public school average of 54% (majority Hispanic).