it rose such as a fortified village of medieval origin, here there is the homonymous castle dates back to the X century along the border between Florence and Siena . Because of its position of guard on the Val di Pesa, this castle had a very important role of defence. This is proved by a document wrote in 1172, which says that two brothers Franculus and Galfredus da Cintoia had a loan giving their possessions located in the Volpaia's castle.
In 1250 Florence divided the territory in Leagues, and Volpaia was in the Chianti League, among the people of the Terziere di Radda. It suffered a lot of times the consequences of the wars between Siena and Florence , but the most serious damages were caused by the raids of Alberico da Barberino during the war between the Florentine Republic and the Visconti, and during the Aragonesi's invasions in 1452 and in 1478. In the middle of XVI century the Florentine Republic fell and the castle of Volpaia lost its military function. Nowadays it hasn't any more all its medieval walls, but it preserves a "cassero" an uncovered bridge, situated in the centre of a little square, and a lot of medieval houses. Inside its walls there is the ancient church of Volpaia deconsecrated in the XIV century, when the new church was built. The most important building is the Commenda of S. Eufrosino dating back to the XV century; until the 1932, when it was deconsecrated, there was inside a painting by Cosimo Rossellini, transferred to Florence . Today this building is used for cultural manifestations and also like art gallery.