Castello di Montefiridolfi, Medieval castle in San Casciano in Val di Pesa, Italy.

Castello di Montefiridolfi is a stately residence outside the village of Montefiridolfi, reached at the end of a short cypress avenue. It is a massive construction with buttressed corners and a trapezoidal plan, with two inner courtyards, each with an artesian well, plus the courtyard of the parish canonica. The tower rises over the upper courtyard; its height was greatly reduced and its top plastered. Few openings pierce the body, mostly at ground level.

The Buondelmonti family owned the fortress from 1015, establishing their power in Tuscany. By 1480, it served as an ammunition depot before gradually losing its military importance.

The name Montefiridolfi derives from the Latin Montis filiorum Ridolfi, meaning "mountain of the sons of Ridolfi", as recorded in a 1210 document from Badia a Coltibuono. A local rhyme, "Monte montoro, entro tre pozzi un vitello d'oro", refers to the three wells in the castle courtyards.

The castle stands outside the present village of Montefiridolfi, reached at the end of a short cypress-lined avenue. The main building is privately owned by the Rosselli Del Turco family, so visits concern the exterior and the surrounding walled complex, which also enclosed the church of Santa Cristina and the parish canonica.

The castle's two inner courtyards each have their own artesian well, and the lower courtyards were added only when the building changed from a military post into a villa and farm. A local rhyme recalls this: "Monte montoro, entro tre pozzi un vitello d'oro" — three wells, counting the one in the parish priest's house.