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The events linked to the building of the Church only partially altered the layout of the district. The square had been built to meet the needs of the Augustinian monks and the inhabitants, so the square as well as Via Maggio, were used for the wool market during the fair of St. Martin's feast day. The presence of a "stove", between Piazza Frescobaldi and II Fondaccio, was mentioned as far back as the records of the 13' century. The "stove" was used as a sauna but later was also used as a house of ill-repute.

The square, as we see it today, didn't have a regular profile. In the middle of the 14' century, it was probably still crossed by a small street that was the continuation of Via Michelozzi, crossing Via Maffia to join Via Santa Monaca. This street divided the buildings on the western side of the square, leaving the Monastery on the right, and the buildings used by the monks as laboratories on the left. These buildings took up two floors which had vaulted ceilings and Gothic windows on the upper floor.

This long building actually took up all the western side of the square as far as Via Sant'Agostino. It contained an oven to bake bread for the poor and pilgrims, stables for the Monastery and a hospital for the sick. If we give credit to the tradition, Michelangelo often visited the place at night to study the anatomy of the corpses that had not yet been buried and, for this reason, he donated a wooden Crucifix to the Prior, which is among the Church's works of art. The Manfredini family built a chapel on the corner of Via Sant'Agostino. On the external wall facing the square there was a shrine with a fresco by Giottino that, according to some scholars, was later moved to the corner between Via del Leone and Via della Chiesa. At the end of the 16" century, the whole structure was raised by one floor and transformed into dwellings. A Loggia was then opened on the corner of Via Sant'Agostino. The whole project was designed by Alfonso di Sante Parigi (the architect who completed the Uffizi after Vasari's death) and by his son Giulio who also built the Chiostro dei Morti in the adjoining monastery in the first decade of the 17' century.