| Name | Address | Enrollment | Grade span |
|---|---|---|---|
| Chapman School | 38 Country Club Road | 380 | 1-7 |
| Cheshire Correctional Center School | 900 Highland Avenue | 27 | 10-12 |
| Cheshire High School | 525 South Main Street | 1,273 | 9-12 |
| Darcey School | 1686 Waterbury Road | 663 | PK-1 |
| Dodd Middle School | 100 Park Place | 822 | 7-10 |
| Doolittle School | 735 Cornwall Avenue | 590 | 1-7 |
| Highland School | 490 Highland Avenue | 956 | 1-8 |
| Humiston School | 30 Spring Street | 18 | 6-12 |
| Manson Youth Institution School | 42 Jarvis Street | 508 | 8-12 |
| Norton School | 414 North Brooksvale Road | 477 | 1-7 |
| Webster Correctional Institute School | 111 Jarvis Street | 7 | 12 |
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