The old Middletown High School was built in 1894-1896 on the southwest corner of Court and Pearl Streets. The Romanesque Revival-style building was designed by the Hartford architectural firm of Curtis and Johnson. Additional wings were added in 1912 and 1931. The 1912 addition matches well with the original structure, but the 1931 addition stands out more as a newer separate construction. The building served as a school until 1972, when a new high school was built. In 1979, the old school was sold to a developer and converted into apartments for elderly housing.

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Old Middletown High School (1894)