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The Oliveto castle, really more a fortified villa than a castle, was built in 1424 on the top of a hill dominating the inner valley of the Pescaiola stream, tributary of the river Elsa, by the Florentine nobleman Puccio Pucci, to protect his properties and to be used as country residence or refuge in case of politic bitterness in Florence.
In the Middle Age the castle was one of the most important stronghold of the Aretine countryside, due to its position it was able to exercise the control on the Valdarno and the Val di Chiana.