In 1604, the monastery of San Silvestro was handed over by Pope Clemente VIII to the new Italian congregation of the Barefoot Carmelites, which spearheaded the reconstruction work on the building, re-founding the convent wing, and then the ecclesiastical building, completed in 1660.
 
The area given over to the picture gallery (Pinacoteca), together with the choir stalls and the convent Church itself, contains an important collection of sacred paintings from the 18th century, illustrating different styles while nevertheless linked by the common denominator represented by the relevance of the Withdrawal of St. Silvestro and the fact that the paintings were made specifically as a devotional tools.

Most of the works are on small canvases, made for the worship and devotion for the members of the Barefoot Carmelite community or for religious people who spent time in reflection and withdrawal from daily life at the monastery. The images of prayer, donated by various convent rectors or benefactors, form a gallery with pictures hung on three walls of a huge rectangular hall.
 
The oldest is the small painting of the Virgin Mary sitting with baby Jesus and Joseph between Saints John the Baptist and John the Evangelist.
 
A series of paintings from the Caravaggio school or style, dating back to the years of Paul V’s papacy (1605 - 1621), once included the St. Jospeh the Carpenter (San Giuseppe Falegname) by Gerrit van Honthorst, which was stolen in 1976.

There are two original Caravaggios featuring the Supper at Emmaus (Cena in Emmaus), one of which faithfully reproduces the painting Caravaggio made of the same subject, now to be found in the National Gallery in London. Also noteworthy are the small canvases with the Four Doctors of the Church (Quattro Dottori della Chiesa) and the Coronation of Thorns (Coronazione di spine), attributed to the French-Flemish circle by Bartolomeo Manfredi. The body of works by the painter from Perugia, Gian Domenico Cerrini, date to the mid 17th century, showing classical tendencies inspired by Bologna models, including the Maddalena penitente, the Christ at Colonna and the Prayer of Christ in the Garden (Preghiera di Cristo nell’Orto, in the capitular hall).