The Annunziata church and its former convent rise on the area of Ascoli Piceno reserved for important religious buildings in Roman times.

In the mid-thirteenth century, the Augustinian nuns built the first church of SS. Annunziata and the minor cloister. In the second half of the fifteenth century, the complex passed to the Observant Friars Minor who built the new one between 1485 and 1505 to replace the old church, the remains of which still can be seen on the right- hand side of the building. The Friars Minor owned these buildings until the unification of Italy, when the Order was suppressed. In 1881 the complex became the seat of a school of agriculture and, in 1926, it was used as an orphanage. Restored by the municipality in 1998, the complex has become the seat of the Faculty of Architecture of the University of Camerino. The Convent, preceded by a portico with eight arches, includes two cloisters. The smaller one, dating back to the fourteenth century, is supported by octagonal pillars and, at the center, it has a beautiful  fifteenth century well. The cloister, attributed to the late fifteenth century, is coeval with the current church. Noteworthy: a fresco by Cola dell'Amatrice depicting "The ascent to Calvary" and “The Annunciation "by Crivelli, now in the National Gallery of London.