Old Middletown High School
This building occupies the southwest corner of Court and Pearl Streets. It is situated in a modestly scaled nineteenth century urban residential neighborhood. Although integrated into its surroundings, the old high school stands out because of its size and Romanesque styling.

Built in 1894 - 1896, this building was Middletown's second high school. The Hartford firm of Curtis and Johnson designed the structure in Romanesque style. The building for which no expense was spared in materials or design, set an innovtive standard for the educational facilities of its day. The use of different materials ( Pompeian brick, brownstone, and terra cotta) produces a rich textural effect on the exterior. A turret on the northest corner, the use of round compound arches, and an overall asymmetrical plan are typical of the Romanesque style. In 1912 a large wing designed by Charles Scranton Palmer of Meriden was added to the south side of the building. This wing closely repeated the materials and stylistic elements of the existing structure. A second large wing containing a library, auditorium, and gymnasium was added to the west side in 1931. Although it incorporates some Romanesque details such as sound compound arched windows and utilized materials compatible to the original, the overal impression is of a separate and distinct construction. The old high school is one of the few monumental civic buildings of the nineteenth century remaining in Middletown and the only one of the Romanesque style. It ceased operation as a high school in 1972.

Current Use and Condition
In 1978 the High School was converted in to apartments for elderly housing and the structure remains in good condition.