Medieval Italian city-states with access to the sea, most notably the Venetian and Genoese, were in need of safe ‘stopovers’ that would allow their inhabitants to travel to distant places across the territories in which they conducted commerce. As the most important ‘stopover’ and centre of consumption, Constantinople became a point of attraction for Italian merchant colonies, particularly after the eleventh century. Among these, the most powerful one with the largest settlement was the Venetian colony. Following a decree dated 1082 (Chrysoboullos) that granted them certain privileges, the Venetians settled across the southern shores of the Golden Horn. In terms of administration, it appears that, until the Latin period (1204–1261), no formal officers were appointed to the Venetian Merchant Colony. ‘The bailo’ was first instituted in Constantinople only after the treaty of 18 June 1265. The mention of a house owned by the bailo dates as late as 1277. Documents on the residence of the bailo remain silent until the early fifteenth century. It is unclear if the palace of the bailo mentioned in fifteenth-century documents and the house allocated to the bailo in 1277 are the same building. Despite the Turkish conquest of Constantinople in 1453, the Venetians, albeit with interruptions, continued to live on the historic peninsula. However, it is no longer possible to speak of a Venetian settlement similar to the one that had existed in Byzantine times. Per the agreement signed on 16 August 1454, the Venetians were granted a house and a church that ‘once’ belonged to Anconitans. The possible location and architectural features of the residences of the bailo, which have left behind no archaeological data, are discussed here through written sources including Ottoman documents.