The church of Santa Maria Assunta in Montescudaio was mentioned in 1092 and also attested in the 14th century, in 1416 the church of Sant'Andrea in the castle he inherited the title of the suppressed monastery for women named after the Virgin. Until 1837 the church of Montescudaio preserved a double title: was the parish church of Sant'Andrea, and at the same time, the abbey of Santa Maria Assunta. The earthquake that in 1846 razed the high part of the country also destroyed the church.
The new church dedicated to Santa Maria Assunta, was built from 1854 to 1857. Wider than the previous one and with a Latin cross plan concluded from the apse, has the facade facing west, preceded by a wide staircase. Inside you will find a statue eighteenth century marble painting depicting San Francesco di Paola, by an unknown author, and a canvas depicting the Annunciation, attributed to the Venetian school of the Seventeenth Century.