Castello di Oliveto, 15th century fortified villa in Castelfiorentino, Italy.

Castello di Oliveto is a 15th century fortified villa near Castelfiorentino with four tall crenellated corner towers and red brick walls. The structure sits on a hilltop above the Pescaiola stream valley and combines defensive towers with a residential complex arranged around a central courtyard.

The castle was built in 1424 by the Pucci family, a Florentine merchant household, and initially served as a fortified residence. It changed hands in 1850 through the marriage of Paolina Pucci to the Guicciardini family.

The castle's name comes from the olive groves on the surrounding hills. Since the 15th century, the Pucci family used it as a country residence, and today it operates as a farm producing wine and oil. Visitors can tour the vineyards and olive groves and see the production process.

The castle stands on the road linking Castelfiorentino to Certaldo, on the hills above the Elsa valley, and is reached by car. Access is through the main gate into an enclosure and then the inner courtyard. The property is rented out for receptions of various kinds, so visits depend on events being held there.

An underground passage connects the courtyard well to the valley below and was originally designed as a secret escape route during medieval conflicts. This hidden passage lets visitors see the practical security measures residents needed back then.