Montegonzi whose name has Lombard origins, it was a fief of the counts Guidi as confirmed by the Imperial diplomas of Arrigo VI of 1191 and Frederick II, 1248; the village surrounded by walls during the 13th century develops around the Castle.
In the middle of the sixteenth century became part of the League of Avane to then become its capital. The Mayor appointed by Florence resided in a palace which still exists.
The keep was built before 1000, as can be seen from a parchment preserved in the State Archives of Florence.
Montegonzi originally was supposed to have a structure very similar to that of Monteriggioni, with walls and keep, which were to serve as a last bastion. In the walls there were, at the main access routes to the country, the doors, in number and size in proportion to the extent of surface and texture of the population.
Walking in the narrow and cobbled streets within the village there is the Palace where the officer in charge of the League of Advanced; in the front door, surrounded by a stone arch, can be seen the coat of arms of the League of Avane. Of the three entrances to the village remains survived the so-called “Porticciola“ because of its modest size.