Next to the church is the cloistered monastery founded in 1503 and later expanded during the life of Caterina de’ Ricci. The atrium leads to the Papalini Madonna Chapel. Legends hold that the chapel houses a 16th-century maiolica bust that caused the Spanish troops of Ferdinand II of Aragon and Pope Julius II to spare the monastery during the 1512 Sack of Prato. The altar has two panels depicting and "Assumption" and "Scenes from the Passion" (circa 1576) by Michele delle Colombe; it also houses precious paintings by Simone Pignoni ("Saints Catherine and Tecla"); Lorenzo Lippi ("St Francis di Sales"); Ridolfo del Ghirlandaio ("Madonna and Child"); as well from the studio of Giovanni Battista Naldini. There is an altarpiece by Michele Tosini in the garden of the Chapel of Madonna di Loreto. Some sites in the convent are closed to visitors.