Tuscan Chianti Estate, San Casciano Val di Pesa, Italy

Cypress trees, vineyards and lush forest define the landscape of Chianti Classico — a small hilly region considered the birthplace of Tuscan winemaking. This grand estate is in the Sangiovese-producing region, just half an hour’s drive from Florence and a 45-minute journey from the medieval Tuscan city of Siena. The 13th-century estate covers more than 12 acres of land containing olive groves, vines, private woodland and four formal gardens — Giardino Secreto, Lavender Garden, Rose Garden and Parco Romantico — featuring marble fountains, sculptures and three swimming pools with terraces overlooking the Chianti hills. One sculpture, The Horse, is a legacy of former owner and Dutch painter Karel Appel, who lived here from 1989 to 2000. Appel resided in one of the ateliers, but this is just a pocket of the sprawling estate. Covering 20,000 sq ft, the property encompasses two villas, three ateliers and the historic Fattoria Marzocca building, which houses four apartments. All interiors have been thoughtfully renovated by local artisans using fine Tuscan materials.