The castle was built shortly after the year one thousand as a possession of the Aldobrandeschi family. Their control over the fort was over in the second half of the thirteenth century as a result of a violent siege by the Sienese.
Montemassi castle comes in the form of imposing ruins restored to their former glory, thanks to the recent restoration work.
The complex is delimited by a series of curtain walls which enclose a large fortified courtyard, the location of a series of buildings with arched doors and windows; in this area we are also visible remains of a tank for the collection and distribution of water.
The historic center of Montemassi is quite picturesque for keeping still the appearance of a compact village “pine cone” without remaining traces of the walls, largely incorporated in the home, except for a door, which once protected him and linked to the castle