Next to the Church of St. Augustine, on the southern side, it is possible to see  what was once the Augustinian convent—a place with a fascinating history. Today it has been transformed into private residences, yet it still manages to tell the story of its past.

The construction of the convent began in the 14th century and was made possible thanks to a generous donation by Bacco del Priore, a nobleman from Siena, who in 1332 left several nearby buildings to the friars—structures that were later incorporated into the new complex. Since then, the building has undergone numerous renovations and modifications, resulting in a complex architectural stratification.

At the heart of the convent was an inner cloister, around which the monastic spaces were organized. The oldest parts can still be identified today in the eastern wing of the building, which runs perpendicular to the southern side of the church. Here, one can find original masonry in filaretto stonework and lowered travertine arches—elements characteristic of 13th- and 14th-century architecture.

During the 19th century, following the Napoleonic suppressions, the convent was decommissioned and later converted into residential housing. Despite these transformations, it is still possible to perceive its original function and appreciate its historical and architectural significance.

Walking through the surrounding area, one can spot ancient materials and architectural details that tell the story of centuries of religious, civic, and urban life in Asciano.