The name Villa Il Cerretino comes from the word “cerri”, the local dialect name for the type of oak tree found in the woods surrounding the villa. Because of its strategic and dominant position on the outskirts of Florence, over the centuries the villa has changed hands many times and undergone incredible architectural transformations that can be seen in the rooms and atmosphere of the house. The military architecture of the late fifteenth century is mixed with elements of farm style buildings as well as the noble villa style typical of the sixteenth and seventeenth centuries. In the fifteenth century the complex belonged to the Bini family, of which various coats of arms remain on the tower and in the internal courtyard. It then was sold to the Medici to whom the reputation of the villa was forever linked when Grand Duke Francesco I made it the residence of Bianca Cappello, the Venetian noblewoman who was his mistress and eventually his second wife. During the sixteenth century the Villa was renovated and typical elements of the period were added such as the large kneeling windows on the eastern and rear sides and a new upper lawn outside the main floor of the villa.

In the eighteenth century the villa was sold to the Moldetti family. They were responsible for the adaptation works to the Chapel, the eastern tower and the central Belvedere of the lower garden. The ceiling of the small chapel, dedicated to San Francesco di Paola, was also decorated internally by a Florentine artist. In the following century the Villa passed to the Contini Bonacossi family and was used as a farm. In fact, the 20 hectares of land surrounding the villa were used to produced wine (we are in what is now designated as the Carmignano DOCG wine region), and Tuscan extra virgin olive oil. At the end of the 1960s, the Villa was purchased and restored by the current owners and after initially being used as their own private residence was then transformed into an exclusive location for events and holiday stays.