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Castiglion Fiorentino of Roman origin, known from 1014 as Castiglione Aretino until, in 1384, when Florence took over the Aretine Republic, it became Fiorentino. Its medieval girdle of walls, dominated by the Cassero fortress, remains intact. The historic centre consists entirely of dignified mansions, both sacred and secular, among which the most notable are the Gothic church of S. Francesco (Saint Francis), the Collegiate church and the Gesų church, all of them rich in art works of high value.
In the 16th-century Palazzo Comunale there is a rich library with paintings, tablets and priceless goldwork of the 12th to 15th centuries. A short distance beyond the walls is the church of the Consolation (Renaissance) of octagonal plan.
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