Situated on the south-eastern slope of Montauto, Villa La Barbolana was built between 1556 and 1582 by order of Federico di Antonio Barbolani on an estate belonging to his family since the 13th century. Surrounded by agricultural land, the villa, apart from being an aristocratic residence, operated as a farm for a long time.

The building overlooks the magnificent panorama of Valtiberina and is an example of fortified structure featuring the characteristics of the villa, of the palace and of the castle at the same time. Four jutting bastions are at the corners of the building, whereas in the centre stands a tower. The villa is accessed by two bridges on the ditch surrounding the building.

The interior features vaulted ceilings and terracotta-tiled floors. Up to the 19th century a private chapel dating back to the 18th century was on the first floor.

During the 19th century the building was renovated on the occasion of the marriage of Carlotta Barbolani and Simoni Francesco Velluti Zati, Duke of San Clemente.