This is an ancient walled town which, as its name suggests, stands on a plain at the foot of the Cesane hills, along the valley of the River Rio Puto, a tributary of the Metauro, some 9 km from the ancient Flaminian Way.
An early plaque records how, in 1204, during the reign of Pope Martin IV, Isola del Piano, which at that time was ruled by the Ghibellines of Urbino, was set on fire by troops from Rimini who had been called to help members of the Guelph forces who had taken refuge in Sassocorvaro. Later the town became part of the Duchy of Urbino where it remained until 1575, when Duke Guidubaldo II Della Rovere gave it in fief to Marquis Camillo Castiglioni of Mantova. It was then passed down to his descendants. Palazzo Castiglioni (today called Palazzo Bartolini)still stands in the town with its fine 16^th Century entranceway. The clock tower next to the Town Hall dates from the same period. The church of the Annunziata, however, is the most interesting building with its Renaissance frescoes, which include a "Madonna and Child, St Francis and three angels" attributed to the studio of Raphael's father, Giovanni Santi.
Isola del Piano was once noted for its stone quarries. These produced a white marble marked with black which was weather resistant and used for external pavements and stairways.