The name Careggi probably comes from "campus regi", which means royal property, probably to highlight a hunting area used by medieval gastalds.
In 1417, Giovanni di Bicci dei Medici had bought the property from Tommaso Lippi; Cosimo the elder, Giovanni's son, commissioned Michelozzo to transform the villa.
During the reunification council of the Eastern and Western churches of 1439 that was held in Florence, about eight hundred learned people from all over the world stayed in the city for about two years, which led to the rediscovery of the ancient Greek-Alexandrian texts. Plato's Dialogues were immediately translated by Marsilio Ficino, who, acting on the orders of Cosimo the Elder, founded the Neoplatonic Academy in 1462. It was first located in Villa le Fontanelle, but its main location became the Medici Villa of Careggi. Among the representatives of the reborn Academy of Athens, there were Pico della Mirandola, Poliziano, Nicola Cusano, Leon Battista Alberti, Cristoforo Landino, Bartolomeo Scala and representatives of the Medici family, such as Lorenzo the Magnificent and Giuliano dei Medici. A panoramic loggia, attributed to Giuliano da Sangallo, was built in the Villa of Careggi, to accommodate the numerous students at the Academy. The building demonstrated a new relationship between architecture and nature that, thanks also to the rediscovery of the ancient texts of Vitruvius, became stronger during the Renaissance years.
In 1529, a fire caused extensive damage to the villa. Later on, the property belonged to the Grand Duke Ferdinando I and, in 1609, it passed to Carlo dei Medici who, after being appointed Cardinal in 1615, planned important restructuring of the villa.
As with the other Medici villas, here too, there is a formal Italian garden and a large English-style park in front of the facade, surrounding it on all sides.
Over the centuries, the Villa di Careggi did not maintain the splendour of a prestigious location that welcomes the brightest minds. After the Lorraine dynasty, it was sold to Francis Joseph Sloane, a collector who made his own architectural changes. When he died, in 1871, the villa went to Augusto Bouturlin and then to Carlo Sergè in the twentieth century. In 1936, the villa became the property of the Arcispedale hospital of Santa Maria Nuova until 2013, when it was purchased by the Tuscany Regional Authority.