The most ancient documentary record dates back to 1088, when a deed was drawn up “a castro Monteficalli” .The castle was mentioned several times in the early 12th century as a place where official deeds were compiled and signed. Over the following centuries, the castle and the village of Monteficalle belonged at various times to the Ricasoli, the Benci of Figline and the Gherardini of Montagliari families.
The village grew up along a road called Via del Guardingo di Passignano that connected the three main valleys in the southern part of the Florentine countryside, the Val d'Elsa, the Val di Pesa and the Val di Greve, with the Upper Valdarno.
The castle, first known as Monteficalle, began to be called Montefioralle in the 18th century.
The village developed around the highest part of the hill, which was the ancient feudal village, assuming an elliptical shape around a radial street with narrow lanes branching off from it, the whole running down from the feudal castle. The village is surrounded by walls that follow its shape. In the portions of walls still standing today are the remains of towers, now converted into houses, and the three gates all opening directly in the walls. The walls, entirely built of hewn stone, date from the late 13th century-early 14th century.