The ancient Monastery of Santa Chiara, now home to the Circolo di Fratellanza Artigiana and private residences, is easily recognizable by its elegant rusticated portal at number 25, the only original entrance to the complex.

The monastery was founded in 1627 at the initiative of Canon Silvio di Monte, who donated his house—previously belonging to his uncle Pietro di Monte, Grand Master of the Order of Malta—to establish a cloistered convent. The adaptation works were probably overseen by the Aretine painter and decorator Teofilo Torri, who mentions a monastic construction site in Monte San Savino in his Ricordanze of 1612.

Originally, the complex also included a small church with a bell tower, identifiable with the present Oratory of Sant’Onofrio (or Santa Barbara), accessible from the Church of Santa Chiara.

Initially dedicated to the Immaculate Conception, the monastery later took the title of the Purification of the Virgin Mary, as a Benedictine convent under the same dedication already existed in the town. The nuns followed the Rule of Saint Clare according to the bull of Pope Urban IV.