The fortified village of Montelifrè rises along the SS38 between Trequanda and Montisi, is can be reached from Sinalunga [ exit 'Val di Chiana/Bettolle' of A1 ] traveling throughout the SS38 toward S.Giovanni d' Asso/Torrenieri or from Siena throughout the scenographic route going along Asciano and San Giovanni d' Asso.
The small village of Montelifrè stands on the
road that connect the villages of Trequanda
and Montisi, between the Val di Chiana and the territory of the
'Crete Senesi' in the Val d' Asso, crowning a rocky hill and is overlooked
by the imposing ruins of its ancient castle. Its name derives from the
one of an earlier feudatary, Liutfrido, in German 'Liutfred', translated
in 'Lifrè'. In some reports the castle is called also Monterenfredi.
In the April of 1527, during the last war between Florence and the Republic of Siena, the fortress, just located on the border between the territories of the two fighting sides, was once again the den of Siena's enemies and refuge for exiled, rebels and outlaws. The Sienese Army, taking advantage on a momentary defeat of Florence, besieged the fortress and, after its surrender, shaved it to the ground mining the walls. Since that time, huge and with still part of its original stone revetment, the ruins rise scattered on the ridge and the northeast part of the relief. On the opposite side developed the small village enclosed by town walls gifted with two gates. Today the whole complex, castle and village, is a private property, transformed in holiday homes, visible only from the road.