The village occupies the top of a hill on the southern side of Montalbano and bears traces of its origins as a castle from the Middle Ages. Leonardo represented Montevettolini bearing the forms of a village surrounded by walls, both in one of the maps representing the lower course of the Arno and in the famous Landscape, executed in his youthful years, dated to the year 1473.
The shape and constitution of Montevettolini in the Late Middle Ages, as reconstructed on the basis of material traces and written sources, seems consistent with the hypothesis that this castle is the one represented by Leonardo in the famous 1473 drawing, Landscape (Florence, Galleria degli Uffizi, Gabinetto dei disegni e delle stampe, n. 8P). It is believed that the panorama represents a glimpse of Fucecchio Marsh taken from the elevation of the Belvedere, on Montalbano, with part of the defenses of the castle of Montevettolini visible to the left of the drawing, while on the right, in the distance, the castle of Monsummano would have been represented, on top of an upside-down cone shaped elevation. This hypothesis is supported by observations related to the best known of Leonardo’s bird's eye maps representing the middle Arno Valley, such as, for example, The Valley of the Arno, Windsor Castle, RL 12685.
The scant information about the origin of the castle village make reference to the consortium called the lambardi of Maona/Montecatini which, at least from the second half of the 12th century, appeared to hold rights on Montevettolini. Nonetheless, a document from the early 13th century (1220), when the castle was already equipped with municipal institutions, highlights the rights that the Alberti family, in the collateral branch of the so-called Counts of Capraia, held on the village of Montevettolini. The reference document was a denunciation of harassment the community suffered from the noble family, and in particular by Count Guido Burgognone. The community of Montevettolini was represented by a prosecutor, who turned to the podesta of Lucca for resolution of the dispute. Two years later, in 1223, the inhabitants of Montevettolini refused to become part of the territory subjected to the city of Pistoia. Montevettolini was, in fact, like the nearby Monsummano, on the border disputed at that time between the cities of Lucca and Pistoia. The representatives of the castle, now organized into communitas, intervened in the relations with the two cities, which, in those years, competed for the Valdinievole in the construction of their respective contados. As happened for the nearby Monsummano, another castle of the Alberti, Montevettolini, as well, built strong ties with the city of Lucca, greatly limiting the expansionist ambitions of Pistoia in the territories beyond the ridge of Montalbano. Thus at the end of the 13th century, the territory belonging to the castle of Montevettolini still marked the border between the two cities. A document from 1283 describes a detailed controversy for verification of the boundaries between Montevettolini and Serravalle, or between the districtus or comitatus of Lucca and Pistoia. At that time, the castle must have had an important demographic weight, as evidenced by documents reporting the value of the census owed to the diocese. Furthermore, the magistracies of the young local government had their own statutes..