The earliest evidence of settlements in the territory of Castiglion del Bosco dates back to the Etruscan period: the castle of Castiglion del Bosco, still perched atop the village as the symbol of the estate, was built in 1100.

In the following centuries, significant and influential families from Siena dwelled in the property, shaping its artistic history and its agricultural heritage.

After years of producing wine solely for domestic consumption, in the second half of the 20th century, a new vision for the wines began to catch on: in 1967 Castiglion del Bosco was among the founding members of the Consorzio del Brunello di Montalcino.

Since then, Castiglion del Bosco has continued its winemaking journey that led, in 2003, to Cecilia Leoneschi taking over vineyard management and winemaking. Castiglion del Bosco has been the place of choicefor Brunello in the northwestern part of the denomination ever since, carrying the historical memory of undivided lands across the centuries.