Orange Street Between Wall Street and Grove Street-East Side

Sanborn 1886 Map:

1879 Bird's Eye View:

This street only contained two buildings, Hillhouse High School and a small house that faced Grove Street. The Farmington Canal which ran through the block prevented any further construction.

Hillhouse High School

Status: Demolished, 1939

Built for: Hillhouse High School, 1871, by Rufus Russell

Hillhouse High School for decades was New Haven's primary high school building. Constructed in 1871 and designed by Rufus Russell, it replaced the former Lancastrian School building (only just barely seen in one image). Russell, one of New Haven's chief institutional architects of the later 19th century who apprenticed under Henry Austin, designed the school in a free Victorian Gothic mode with a Second Empire mansard and clock. The brick façade with stone banding and carved details was characteristic of grand Gothic buildings being built in England. The design featured a dizzying array of window arrangements and a strong articulation of floors, with rustication on the first, creating a powerful base, intermediate floors that closely resembled each other with paired windows joined by segmental arches, and a taller upper story with elaborate window treatments capping the whole. Slightly jutting pavilions marked the entrances, decorated with more carving and ornament to indicate their status and reflected by small pediments above the cornice. The school was put to other uses when a new high school was constructed in York Square and was finally demolished in 1939. Images of the school can be seen here and here. 

Photo: Wikimedia

Block Survival Rate: 0/2: 0%