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Abstract: This paper analyses a series of documents, mostly unpublished, which have made it possible to place a new piece in the puzzle of the house in which Caravaggio lived, in Vicolo di San Biagio in the Campo Marzio quarter, between the 8th of May 1604 and the 26th of August 1605, at which date the painter was evicted after a prolonged dispute over rent arrears. The recently discovered documents have revealed that the first owner of the building was the jurist Laerte Cherubini, who commissioned the altar panel The Death of the Virgin and, several years before he commissioned this painting from Caravaggio, sold the house in 1593 to Prudenzia Bruni, wife of a leather merchant called Bonifacio Sinibaldi. Prudenzia divided the property into two separate apartments, one of which was intended as a source of income, as confirmed by the rental contract drawn up with Merisi in 1604. This study reconstructs Prudenzia Bruni’s family and property. Her relations with her tenant, Caravaggio, were stormy, and worsened when he disappeared after injuring the notary, Pasqualoni, who was a rival for the affections of Lena, «donna di Michelangiolo». More information has also come to light with regard to this young woman, Lena, who probably posed for him in the Vicolo di San Biagio house for the painting The Madonna of Loreto in the church of Sant’Agostino; it is now possible to supply further documentary elements which identify with greater precision where, according to the statement given by Pasqualoni, she stood in piazza Navona during Caravaggio’s assault on the notary.