Traces of human settlements in the town of Pieve Santo Stefano date to the Neolithic and testify the ancient story of a land that was the favourite place of both the Etruscans and the Romans to establish important built-up areas. Besides numerous archaeological finds that can be linked to these ancient populations, also the Collegiata of Santo Stefano and the XVII-century Santuario dei Lumi can be visited.

In the Roman times, this area became important after the development of wood trade. The village rising at the confluence of the Tiber and the Ancione watercourse was rich in natural resources and became the outpost for the shunting of logs directed to Rome to be used for the construction of temples and houses.
In the XVII century, an ancient gravestone, now lost, was found and gave evidence that a worship centre had been built in Pieve Santo Stefano as established by a man called Publio Sulpicio. It must have been the original nucleus of the Roman settlement.
With the fall of the Western Roman Empire, the Ostrogoths occupied the territorial division of the VII Kingdom of Etruria, to which Pieve belonged. They started a long fight with the Byzantines that resulted into a long battle fought at the half of the VI century A.D. At the end of the conflict, the Byzantine emperor Justinian tamed this Barbarian tribe and founded the province of the "Alpes Appenninae".
Pieve was cited for the first time in 723 A.D in an act according to which the area belonged to Umbria and, therefore, it was included in the Byzantine "corridor" that linked Ravenna to Rome and that divides Italy. At that time, the centre corresponding to the chief town was called "Suppetia", namely "supplier", in reference to its still lively wood trade. Since the VII century, yet, the Lombards led by Liutprand could defeat the Byzantine block and conquered the Valley of the Tiber before Charlemagne's Franks substituted them politically and Christianity dispossessed them spiritually.
Nevertheless, it was thanks to the "Historia Longobardorum" by Paolo Diacono if today we know an "oppidum", namely a wide fortified village that the Lombards re-named "Verona", had developed at that time near Pieve. At the beginning of the year 1000, the "Massa Verona" was ceded Goffredo d'Ildebrando, a supporter of the German emperor Otto I, who rose to the rank of ruler of a wide area in the Tuscan-Emilian Apennine. The spiritual administration of the village, instead, remained in the hands of the curia of Cittą di Castello.