Boston Technical High School remained there until 1987 when it relocated to a new building at 55 New Dudley Street (now Malcolm X Boulevard).

[2] As part of a larger plan to reorganize Boston public high schools, in June 2023 Mayor Michelle Wu and Superintendent Mary Skipper announced a plan to relocate the O'Bryant school from its Roxbury location to a new site at the former West Roxbury Educational Complex on the southwestern edge of the city.

Proponents of the plan cite that the fact that the relocation will allow the Madison Park Technical Vocational High School to double in physical size by becoming the sole occupant of the Malcolm X Boulevard campus while also offering the O'Bryant newly renovated facilities and the capacity to enroll up to 1200 additional students in its new location, initially scheduled to open in 2026.

[3] Many O'Bryant students and parents have voiced opposition to the plan to move the school from its current location in the predominately Black neighborhood of Roxbury, serviced by multiple MBTA bus lines as well as the Orange subway line and the commuter rail, to the predominately white neighborhood of West Roxbury, which is not easily accessible using public transportation.

Additionally, many cite the historical and cultural value of its current home in Roxbury near Nubian Square as a strength of the school and its function in serving a majority nonwhite student population.