The convent complex dedicated to Sant’Agostino stands just outside the city walls, not far from Porta Romana.
The building has undergone various alterations over the centuries but was built entirely in the second half of the 13th century, from around 1251 to 1294. The current facade is attributable to work carried out in the 18th century.
The church has a single nave, with a rectangular apse and a covering of wooden beams resting on pointed arches supported by pillars. It is decorated on both sides by chapels built in the 16th century that protect exceptionally beautiful works of art attributed to various artists: on the left side is Gesù e la Samaritana by Virgilio Nucci (1580) in the first chapel and the Madonna del Soccorso by an unknown artist (15th century) in the fifth; on the right side we find the Madonna di Grazia by Ottaviano Nelli in the third chapel and finally the Battesimo di S. Agostino by Felice Damiani (1594) in the fourth.
What makes the church special, however, are the extraordinary frescoes on the triumphal arch and apse. The Last Judgment is represented on the arch, a wonderful work attributed to Nelli and his workshop, probably assisted by Jacopo Salimbeni from San Severino. The apse, on the other hand – which reads from top to bottom and from left to right – is occupied by scene di Vita di Sant’Agostino (scenes of the Life of St Agostino), which trace the biography of the saint from conversion to Christianity. The paintings, dating back to 1420, are one of the most significant examples of late-Gothic painting in the city.
Two important Augustinian priests are also buried inside the church: the Blessed Pietro da Gubbio and Blessed Francesco da Gubbio (who lived, respectively, in the 13th and 14th centuries).
The Convent complex next to the church has a very well preserved Cloister housing a cistern in the centre for collecting rainwater and a well – now closed – located to the side. The limestone bell tower seems to be a later architectural addition, datable perhaps to the 15th century. Finally, a small adjacent room the size of a cave hosts a permanent Nativity scene. The idea, developed by parishioners for Christmas 1977, has become a real tourist attraction since the 1980s: it is modified annually with new elements and can be viewed throughout the year .