Restructuring work was undertaken on Palazzo Guerrieri, an 18th century building standing on the slopes of the ‘Seno di Ponente’ hill in the historic centre of Brindisi, a few hundred metres from the quayside of the inner harbour. In 2000, Roman and medieval walls incorporated into the palazzo’s foundations on its north-eastern side were discovered during the excavation of a lift shaft. In the summer of 2001, the Archaeological Superintendency for Apulia opened a trench in the area used as a gymnasium, added to the building in the mid 20th century when it was converted into a school. Brindisi town council financed two excavation seasons (2009, 2010) that uncovered substantial traces of occupation documented by stratigraphic and structural sequences attesting the site’s occupation from the early imperial period onwards, abandonment levels dating to the late antique period and medieval and modern occupation. The structures of a medieval building came to light below the modern layers. These comprised rectangular rooms arranged around a space, probably an open courtyard, adjacent to an area probably used for production activities attested by a small brick-built kiln and surfaces with traces of burning. This complex overlay and incorporated the _opus_ _mixtum_ structures of a Roman building dating to the early imperial period. Its vicinity to the port suggests it could have had a commercial function. The walls delimited rooms with brick-built barrel vaults and depressed arch openings, while the few remains of _opus_ _signinum_ paving were once part of the first floor that had not survived.