[4] The street is believed to derive its curved shape from the embankment that stood outside Dublin's city walls in the medieval period; the modern streets still follow the line of this earthen ridge that was built sometime in the 12th or 13th century.

Leitrim House, the best surviving 18th-century building on the street was built during this period around 1760.

It would have originally had a "Dutch Billy" style roof but was refaced in machine-made brick in c1890.

[8][9] A fire broke out at Moore & Co's garage on Stephen Street on 15 July 1970, one of the 1970 arson attacks thought to have been carried out by the Ulster Volunteer Force.

[10] The Leinster School of Music & Drama was based on Stephen Street between 1982 and 1998.