Castiglioni Castle borders on the territory of the Serra de’Conti area. Attested as a castle since 1289, it was most likely founded after the nearby Fossaceca castle had finally been abandoned. It only became a castle to all effects and purposes in the early XV century, and was built in an organic and unitary manner by the City of Rocca Contrada to defend inhabitants from the hazards of the wars being fought (the castle was occupied by Braccio Fortebraccio da Montone). Castiglioni still boasts its original medieval structure, with well-preserved walls and two lovely fortified gates. The parish church, dedicated to St. Agatha, is home to the Madonna of the Rosary (1589) – one of the finest works of Ercole Ramazzani – and a wooden cross from the XV century. The church of St. Maria della Piana (XIII century), located just outside its walls, is worthy of note for its remarkable rectangular façade, which contains a moving fresco of St. Sebastian attributed to Andrea di Bartolo da Jesi (1474).