The castle of Stertignano and the church of the Santissima Annunziata, where the work titled "Madonna che allatta il Bambino" attributed to Signorelli, is kept, can be visited inside the small town of Magliano, in the province of Grosseto. In the immediate surroundings, there is the Romanesque church of San Bruziono. The most ancient olive tree called "The Witch's Olive" has existed here for 3000 years now.

An Etruscan centre called Heba, which dominated a vast territory, was born near the modern Magliano around the VI century B.C. At the beginning of the III century B.C., the Romans substituted them in ruling the city by settling it and starting a period of prosperity and of economic and demographic growth. Heba's slow decadence started in the first centuries of the Empire and it culminated with the decadence of Rome and the Barbarian invasions.
In the XI century, new information about this settlement, where one of the Counts Aldobrandeschi's castles rose, appeared. An imperial diploma by Frederick II dating to 1221 confirms this. The beneficiary of the emperor's confirmation, namely the Palatine count Ildebrando of the Aldobrandeschi, ceded the castle and his lands to one of his vassals, Bernardino di Magliano, in the same year.
In 1274, a branch detached from the Aldobrandeschi family, called the Santa Fiora, took possession of the castle. Therefore, they started a phase of political and military fight against Siena for the control on Magliano which lasted to the XV century. Siena could take control of the area between 1339 and 1345 and kept it until it surrendered to Florence (1555).
In 1365, the Republic was also obliged to deploy its militia to protect the town which had been assaulted by John Hakwood's English mercenary troops. The Lords of Magliano had started the construction of the walls in 1323 and they were finished in 1400.
Once it was included in the Tuscan Grand Duchy, Magliano was re-feudalized and Cosimo I de' Medici ceded it as a marquisate to one of his troops' generals, Cornelio Bentivoglio of Ferrara. His family owned the feud until 1751, exception made for a short parenthesis at the half of the XVII century. Only the Leopoldine municipal reforms, wanted by the Lorraine once they got the power in Tuscany, allowed the town to issue its autonomous statutes.