To be on the borders of the State of Siena, the castle was attacked several times and taken. The Florentine in the thirteenth century devastated three times: in 1208, in 1233-34 and in 1253. Other destruction took place in 1306, the castle now being refuge of sbandati Guelfi, and again in the fifteenth century, the time of wars Aragonese, and in 1554 during the conflict leading to the fall of the republic Siena. Attached to the Grand Medici, Rapolano continued to be the capital of podesteria included four communities (Rapolano, Serre, Armaiolo, Poggio Santa Cecilia). With the reforms leopoldine podesteria was transformed into a community and, after national unification, in common.

The village seems to have developed from a castle èpartire, stretching westwards from a primitive castle on the top of the hill and that is an isolated, which made significant overlooks square Castellare and circuit by way of Castellare . At the centre of this nucleus remains in a tower mozza fìlarotto with an arched doorway and a window acute arched low side North-East to South-East it is still isolated from homes that run around, but by other parties addossano these are more or less closely, but are unfortunately all rebuilt.
The next enlargement has developed in East-West direction for a length of over 250 m and is surrounded by walls largely still very detectable, although at some point entirely disappeared or changed much, especially for the case that there have been built above or in front, however, even where they exist, are more or less reduced to only base. They are interspersed with five round stone towers, based shoe and cordon higher, except one of those to the north, three of them are in the north side, one in the South and one at West, right next to a door, and a square on the north side. They kept two ports: one in the South-East, placed perpendicular to the walls with arched stone acute, and the other, already cited, in the west, consists of a square tower perforated by an arc round, surmounted by two shelves, maybe the rest of piombatoi Missing and crowned with apparatus to protrude arches on shelves brick pyramid upside down. Within several medieval buildings.

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