The Castle of Montegufoni rises on the remains of the ancient castle of the Ormanni, destroyed by Florence in 1135 during the long battles between the city and the noble families of the Florentine country.

The building still keeps part of its ancient medieval relics, even though it was modified during the years according to the Renaissance taste and it became one of the major links between the two periods of maximum splendour in Tuscany. It belonged to the Acciaioli family, some rich Florentine merchants who created their area of influence in Montegufoni. Niccolò Accialioli, who became the High Seneschal of Naples, was born in the castle in 1310.
The current appearance of the building is due to the renovation works carried out in the XVII century. They included the extension planned by Gherardo Silvani in 1632 and the Baroque changes, wanted by Donato Acciaioli, on the north façade and in the gallery above the porch.
Later, the garden was created and it had waterworks and caves with stalactites. It became the place of many meetings and parties organized by the Florentine nobles. The same painters who worked at the Uffizi, Alessandro Gherardini and Agnolo Gori, carried out the interior decorations in that period. In 1773, the gentilitial chapel was enlarged with the aim to house a collection of reliquaries.
The tower of 1386 underwent a restoration, too. An aristocratic English family, the Sitwell, who commissioned some frescoes to the painter Gino Severini, bought the estate in the XX century. During the Second World War, the castle of Montegufoni was the refuge for the Botticelli's "Primavera" and for other works coming from the Uffizi. This way, they were saved from damage and pillages. The castle became a property of the Posarelli family in 1972 and they have further renovated it.