The monastery of Saint Anne or of the Countesses is the only one left of the five structures that have given the name to Via dei Monasteri for centuries. It was founded by Angelina dei Conti di Montegiove and di Marsciano, and it was already active in 1388. The two cloisters entirely frescoed are remarkable. Inside the church we can admire the fresco of the Virgin enthroned with the Child between St. Anne, Blessed Angelina and angels by Pierantonio Mezzastris. On the sidewalls there are, on the right, San Pietro d’Alcantara, on the left, Madonna and Child and San Diego d’Alcalà, works by Ippolito Lemmi da Coceto. The church also preserves two polychrome wooden statues dating back to the sixteenth century, one depicting the Madonna, the other St. Anne. Connected to the monastery there is an accommodation facility obtained from the fifteenth-century houses of painters such as Niccolò di Liberatore, known as the Alunno, which retains interesting architectural and decorative elements. Until 1798 the monastery housed the famous Madonna di Foligno, painted by Raphael.
