Casale Vemignano commands one of the estate’s most prominent hilltops, offering unobstructed vistas in every direction, from the Castello to Casole d’Elsa, Mensano, even to San Gimignano in the distance. The residential compound of three restored buildings and grounds command an expansive grassy plateau above olive orchards that completely surround the property.

The primary residence is organized around a long, open living area with exposed stone walls subtly sectioned off by arched doorways and windows. Magnificent hardwood doors open onto the pergola or patio for evening dining in the spring, summer and fall. The original forno is adjacent to create a warm and intimate dining experience. Two very large master suites on the second floor combined with two large outer sitting rooms offer each suite complete privacy and stunning views of the countryside. There are courtyards everywhere, including a porch opening off the primary guest quarters.

The North Guest Residence, with a soaking tub fronting a massive arched window, is among the most romantic in all of Tuscany. In a property where there is astonishing architecture at every turn, perhaps most memorable is the dazzling glass tiled infinity pool, pictured above, soaring off one edge of the property into the Tuscan hills.