The most ancient archaeological finds in this area (cult and divination objects) date back to when these hills were inhabited by the mythical descendants of the Lidi people. Many local place names, such as Porrona, Tergomeno, Calatine, Percenna, Trequanda, Tordovana, Elatora and Cetinali come from their language. Incredibly, the local pronunciation of the letter ‘C’ also reflects the Etruscan pronunciation of the letter. There are many ancient tombs in the area surrounding Montelifré at Belsedere, Porrona and at S.Stefano a Cennano.
The necropolis at Poggio Pinci is only a few kilometres away and there is an ancient footpath (which today is part of the Crete Senese Tourist Footpath Network) which starts at Asciano and joins the Via Etrusca that goes from Chiusi to Roselle, to the sea and south to the towns of Sovrana, Sorano and Saturnia. In ancient Roman times the first defensive ‘castrum’ was built here. It would have begun life as a simple fortification on top of a hill but during the Early Medieval period it developed into a shelter for wayfarers, as it was on the road that was used by those travelling from Rome to defend Christianity in the centre and north of Italy.
During the Medieval period Monteranfredi became a castle, although it was destroyed and rebuilt many times. The fortress was very similar to the fortress at Montalcino which can be seen in the distance. The census carried out by Siena’s Government of Nine reveals that in 1323 the castle and its feudal estate consisted of a church (re-built in 1600), houses, farm houses, an olive press, a furnace, coal shed, mills, olive groves, fields, pastures, woods, chestnut woods and small farms.The entire estate was bought by the Tolomeis (a merchant family from Siena) in 1328. This family suffered great losses when their bank went under in 1348 and they sold the estate and all their belongings after the terrible black death to Betto di Martinozzo, a merchant from Montepulciano.
The castle’s history reflects that of the Martinozzo family who were first connected to the Medici and then to the Lorena family. The fortress was destroyed in 1527 by the Sienese but the houses and fort were rebuilt. A silk spinning factory was added at the turn of the nineteenth century and a brick furnace was put in place at the end of the nineteenth century.The hamlet and its surrounding woods still belongs to the same family. They have turned it into an Azienda Agrituristica (an Agricultural Tourist Business) and it’s possible to visit the San Biagio Church, the fortress, a twelfth/thirteenth century tower, the villa, the farm houses and the rich surrounding woods where there are still old mills and ruins of old farm houses buried under the moss and broom.