The oldest testimony of the small village of Montefioralle, in Tuscany, dates back to 1085. The castle of Monteficalli is mentioned several times at the beginning of the twelfth century as a curtis wherein were rogati official acts, documents preserved in the archives of Badia a Passignano. Among these documents that dated 4 March 1122 is of particular interest; in that document is certified the sale of an asset between such a buckets of Gerardo and Gisla of Guinildo together with the mother Ermengarda of was Rolando, the characters of this affair have all a name of Germanic origin so that it is assumed that they were members of a noble family of Longobard lineage. In the next period the castle and the village of Monteficalle was property of the Ricasoli, dei Benci of Figline and of the Gherardini di Montagliari. The village was located along a street called via del wary of Passignano, this road put in communication the three main valleys in the southern part of the Florentine countryside, the Val d'Elsa, the Val di Pesa and Val di Greve with the Upper Valdarno. In ancient times the castle was known as Monteficalle to then become Montefioralle in the XVIII century.
The town developed around the highest part that corresponds to the ancient feudal settlement. Developing around the ancient castle the village took a plant of elliptical shape composed of a radial road from which unfold of alleys all leading to the feudal formwork. Of the ancient caisson today has remained a mighty structure with a rectangular plan which has a coating in filaretto of alberese stone. The complex, scapezzato today and reduced to residential use, should rise between the end of the XII and the beginning of the XIII century. All around the village there are the walls which repeat the shape of the village. The parts of the walls still have preserved the remains of some of the towers, today converted into homes and the three access ports, all open directly in the walls. The walls are entirely made in Sasso scapezzato are from datarsi between the end of the XIII century and the beginning of the XIV . The urban fabric has a style very unitary, characterized by buildings with medieval structures. Between these buildings include a house be deemed to have been the property of the Florentine navigator Amerigo Vespucci and another that has a beautiful portal ogival with above the coat of arms of the Bigallo. The sacred building in the village is the church of Santo Stefano.
In the vicinity of Montefioralle is located the Pieve di San Cresci that still preserves the Romanesque structure, with facade is preceded by a narthex and equipped with two mullioned windows.