The villa was built on an ancient Etruscan-Roman route, and in 1364 it became the castle of Trebbio. The fortress had a fortified wall with an external walkway that connected the tower to two nearby buildings. It was the architect Michelozzo who transformed and built the villa-castle for Giovanni di Bicci dei Medici and his son Cosimo the Elder. In the middle of the 15th century, the Villa del Trebbio was intended for Cosimo's nephew, Pier Francesco dei Medici, and was later inherited by Pier Francesco's grandson, Giovanni dalle Bande Nere, son of Caterina Sforza, who moved there along with his wife Maria Salviati and his son Cosimo, who became Duke of Florence in 1537 and later the first Grand Duke. In 1644, the Grand Duke Ferdinando II sold the farm to the Florentine merchant Giuliano Serragli, who then bequeathed it to the Oratorian Fathers. In 1865, with the decision of the Italian government to suppress the religious orders, the Oratorian Fathers left the castle and the farms to Oreste Codibò, a lay administrator whom they trusted. Unfortunately, at his death, his nephew Leopoldo took possession of the complex and left the property in a state of neglect. In 1886, the heirs sold the Trebbio at auction and it was purchased by Maria Teresa de La Rochefoucauld, widow of Prince Marco Antonio Borghese, already the owner of the nearby villa of Cafaggiolo. The entire complex of the Cafaggiolo and Trebbio farms was resold at auction in 1936 and purchased by Dr Enrico Scaretti, who had the Trebbio castle restored in less than a year, saving it from ruin and recovering its original fifteenth-century structure.