On top of a hill there is an inexplicable shape: it is the Pieve di San Polo in Rosso, whose origin is probably paleo-christian, next to it there is the Arbia. The original Pieve is incorporated in the rests of a fortress. S. Polo was founded by Ricasoli Firidolfi in 1070. In 1176 a peace was stipulated in S.Marcellino and Siena had to give to Florence a part of Chianti and also S. Polo. The Pieve led four parishes, so it needed high incomes because it had the jurisdiction in a very wide area. From 1351 to 1352 Arrigo Ricasoli's sons attacked the uncle Ranieri, of S.Polo, who was very rich. Ranieri resisted and occupied the Vertine's castle, Florence sent there Luca da Panzano and Luigi degli Atti from Sassoferrato, that after a long siege he had to surrender. In 1478, there was the second Aragonese invasion and the Florentine government sent 100 soldiers to S.Polo under the commander Schiavo in order to defend the territories against the attacks of the Sienesi which occupied Castellina, but S.Polo was conquered by them. After five years, S.Polo returns property of Florence . In 1555 with the end of the Sienese Republic , the fortified pieve lost its role. Probably a part of the original pieve was pulled down and it had that shape until today.
The façade and two towers of the pieve demonstrate that this religious building had an unfit function, next to it there is a church very articulated and very high like the walls of a castle. The church has a Romanesque structure, with three naves and an apse, but there are also Gothic characteristics such as the ceiling with several vaults, in the past it housed frescoes representing "The life of Christ".
Near the church there is a courtyard which has on one side, some arches to support the Renaissance upstairs.