The Paradise School bears much historical value because it is one of the 5 one-room schoolhouses that were built in Middletown before the turn of the century. Four of these 5 structures survived. The Witherbee School, built in 1892, was restored and equipped as a turn-of-the-century classroom used by fourth graders in a school program called "Those Dear Old Golden Rule Days."
The Oliphant School, built in 1823, was extremely altered, referring to its one to three rooms inside. Today, it serves as a support building to the Middletown school administration department.

The Peabody School, built in 1794, was transformed into a private residence in 1928 while the Wyatt School was demolished. It now serves as the site of the police and fire headquarters in the town.

Paradise School first served its purpose on December 20, 1875 when the first class headed by Peleg Taylor Coggeshall. was held inside. It served this purpose until 1955. Following this educational purpose, the structure housed the school administration office as well as a storehouse until the school department decided to evacuate it.

The Middletown Historical Society acquired the property in 1976. Newly formed at that time, the Society restored the building to be used as the Society headquarters as well as a small museum.

The Paradise School was listed in the National Register of Historic Places on May 5, 1978.