Near the actual village of Monsanto rose, in medieval time, the huge Castle of Cepperello (whose ruins are still identifiable), greatly damaged in 1260 during the Battle of Montaperti and subsequently abandoned, maybe in the XV century [1-2-3]. After this event, an adjoining sighting tower became more important; around it Vettori family started building the Castle of Paneretta, still intact, squared and with an internal yard and angular towers [4-5]. Inherited by Capponi (and then by Riccardi-Strozzi), in 1597 the Florentine painter Bernardino Poccetti (1548-1612) was entrusted to fresco the court archways with decorations to grotesque . During the Renaissance the external walls were also decorated with false windows and false columns. In the whole of the castle there are also the chapel of 1626 and some rural annexes.
Monsanto’s territory comprehends also San Rufignano’s (or Ruffiniano) Church, a roman building which belongs to Sant’Appiano’s plover . Arisen over a church, already quoted in a document of 998, it preserves its original structure, though a little modified during the centuries, with a nave and two aisles separated by archways on pillars, thanks also to the 19th century restoration works and to the 1934 ones. In XVII century, the central apse, in particular, was substituted by a purse and an open gallery was added on the front. Inside are conserved, amongst other things, ancient astylar crosses (for example a Germanic one of the beginning of the XIII century), a 14th century board with the Madonna with the Infant and Saints Rufignano and Bartholomew and a 15th century wooden Crucifix of Florentine school.