Belonging from 1250 to the Ubaldini family and the then to the Bettini family, who were related to the Ubaldini, the castle of Villanova is a neo-medieval complex built in part on the ruins of a pre-existing castle.

In documents dating back to the 16th century, the castle is represented as a building with a tower dominating small ramparts with an access gate. At present, only a tower, two gates and some parts of the ramparts that once surrounded a no longer existing building can still be admired of the original structure.
In the castle probably lived a large community, since a congregation was headquartered inside the ramparts, where there was also a church dedicated to San Jacopo.

Marquess Ottavio Gerini bought the castle and the church (which had been re-built in 1334) in 1611 and made it a part of Villa Le Maschere, one of the most important villas in the Mugello district.

In the 19th century, architect Carlo Gerini built the present castle in medieval style. The castle was then used as a monastery and as a school for the children living nearby.

After having been abandoned during World War II, the castle was renovated and restored in the 1990s.