[1] The Middletown Woodrow Wilson High School is located in what is now a predominantly residential area south of downtown Middletown, on the west side of Hunting Hill Avenue south of its junction with Russell Street.

It is a three-story structure, built of brick with concrete trim, and covered by a hip roof topped by a small tower and cupola.

Its main entrance is in a prominent Classical Revival portico, with paired pilasters flanking the second and third-floor windows, garlanded panels between those floors, and a fully pedimented gable with modillion blocks and a round panel at the center.

It was designed by Linus Baldwin, of Towner & Sellew Associates, to meet the growing demand for education in the city's more rural outlying areas.

At first considered for use as a junior high school, and had what were then state-of-the-art facilities, including specialized classrooms, laboratory and vocational shop areas, and art and music rooms.