Le Convertoie: Tuscan Villa with Pool & History

Nestled in the Chianti hills, Le Convertoie is a historic 16th-century villa built on the ruins of a medieval castle. Surrounded by cypress trees and vineyards, it offers breathtaking views from nearly every room and its terraced gardens. The villa features 4 spacious en-suite bedrooms plus an additional half bath, a billiard room, air conditioning, and elegant interiors with terracotta floors and wood-beamed ceilings. Outside, guests can enjoy a private pool overlooking the Tuscan countryside, shaded outdoor dining areas, and peaceful corners to relax in the gardens. Just 3 km from Greve in Chianti and 30 minutes from Florence, it’s the perfect retreat for families or groups seeking privacy, authenticity, and comfort—a rare blend of history and Tuscan beauty in one unforgettable property.

Located in the heart of the “Gallo Nero” region, the Medieval complex (XI century) was originated as castle with fortified tower. It sits on a massif “pietra serena” hilltop dominating the surrounding countryside and vestiges of the original castle foundations are visible on the strong walls around.
The location has ancient origins: it was initially built by the Etruscans and later hosted a Roman garrison. Traces of the original Etruscan cobbled road that led from the Lucomonia of Volterra to that of Fiesole have been uncovered at the base of the structure.

The villa sits on the ruins of the ancient castle on a spur of rock and overlooks a beautiful wooded valley. It was built shortly after the original fortress’ demolition, which took place in 1530 during the last war between Senese and Florentine troops. Evidence of the glorious past is seen everywhere, from the gardens to the villa ground floor itself. The last modern restoration took place in 1996. Careful routine maintenances have been regularly scheduled. From December 2012 the site is under the safeguard of the Council for the Preservation of Historical and Architectural Buildings.

The property retains the original interiors with the typical Tuscan manor style: large rooms with plenty of light and sun-drenched bedrooms, terracotta floors, high panelled ceilings on the main floor and exposed beams. Doors and window wood original frames, and details in “pietra serena”, bathrooms with hand-crafted ceramic tiles. The ancient barrel vaulted room built in the rock, four spacious fireplaces and many other details contribute to the charming and warm atmosphere, very much appreciated by Tuscan countryside lovers