Unfortunately difficult to investigate because of the scarcity of documents, but from the fourteenth century we archival sources that allow us to reconstruct the vicissitudes of this religious building.
At the Diocesan Historical Archive of Cortona are preserved the 'pastoral visits' (visits that the bishops had to do every year in all the churches of the territory, to control both doctrinal and material), where from an ancient "Pastoral Visit" the 1337, we find our Ecclesia Sancti Silvestri.
In fact, Eve had the good fortune not to be abandoned, but the Benedictine monastery became a parish church with an oratory, where every year on December 31, the feast of St. Sylvester, was made the parish feast. In 1515, Cardinal Silvio Passerini (Cortona, 1469 to 1529) to increase the income of the Chapter who presided, made annex Ecclesia Sancti Silvestri among the assets of the administration Chapter. For New Year's Eve so began the decadence deprived of his parish (which was sold to the nearby church of San Marco in Villa) and his community, was gradually neglected. In 1983 the building has been ranked among the 50 Tuscan farmhouses worthy of mention for its particular architecture.
In 2002, the Monastero San Silvestro has been completely restored and renovated, leaving intact the traces of its history.