It rises upon a hill that used formerly to be covered by Turkey Oaks which in Italian are called cerro, hence the name of the town Cerreto. The village was called Cerreto di Greti until it became a feudal holding of the powerfull Guigi counts in the 11th century. In the 12th century they had to renounce their claim on Cerreto Guidi when they sold the rights to the commune of Florence.
In 1576 it witnessed a bloody act of murder in the main attraction of the place, the Medici villa overlooking the village. The actors in the tragedy where Paolo Giordano Orsini, duke of Bracciano and his spouse, Isabella de Medici, daughter to Cosimo first de Medici. The former being the murderer, the latter the victim. It was the old, old story of the husband wrecking his hurt pride on his faithless consort. Thus poor lonely Isabella fell in love with her husband’s causin, Troilus Orsini, who paid her more attention than had ever-absent husband. She was therefore strangled in her bed by a diabolical contrivance.
Like other Medici Villas, the Medici Villa of Cerreto Guidi was first built as a summer resort and hunting lodge. It was commissioned in the 16th century by Cosimo the first and the original project was probably by Bernardo Buontalenti. The main body of the villa, with a magnificent view over the Valdinievole, consists of a compact blocks supporting the massive structure of the access ramps, designed by Buontalenti between the 1565 and 1567. It has belonged to the Italian state since 1972 and now houses a museum with numerous portraits of the Medici’s dating to the 16th and 17th centuries.