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The Church of Sant’Agostino is located on Corso Diaz, the main street that cuts through the upper part of the historical centre called Cittanuova. Its construction began in 1299 with the intention of replacing the pre-existing Church of San Pietro all’Orto, which could no longer contain the expanding population of Masseto.
The church represents the greatest example of Gothic architecture in the town after the Cathedral of San Cerbone. The building has a single nave with six large pointed arches supporting wooden beams. The apse, the most beautiful part of the church, with large splay windows and hanging arches, was completed between 1348 and 1351. On the sides, two rectangular chapels, also dating back to the mid-14th century, delimit the building. Numerous are the works that can be admired along all the walls, among which we mention St. Guglielmo by Antonio Nasini, the Visitazione and the Natività di Maria by Rutilio Manetti, the Annunciazione di Empoli and the Fuga in Egitto by Lorenzo Lippi. Besides the works just mentioned, it is necessary to remember that inside the Church there are the relics of San Bernardino da Siena, born in Massa Marittima in 1380.
Two other elements complete the structure: the bell tower, built in 1627 on the ruins of a pre-existing tower, and the cloister annexed to the convent, dating to the beginning of the XIV century, provided with elegant small columns with graceful capitals that support the wooden roof. Today the cloister is often used to host banquets, parties and various events.