Piazza della Madonna dei Monti extends between Via dei Serpenti and Via degli Zingari, taking its name from the Church of Santa Maria ai Monti, which overlooks it on its left side. Despite its small size, its beauty and lively atmosphere make it one of the main meeting points of the Monti district.

The graceful Fountain of the Catecumens, commissioned by Sixtus V in the 16th century, adds to the charm of the place. Designed by Giacomo della Porta, it was sculpted between 1588 and 1589 by the stonemason Battista Rusconi. The octagonal travertine basin rests on a four-stepped base that compensates for the unevenness of the square; the coats of arms of Sixtus V and the city alternate on the sides. In the center, two overlapping basins pour water through lion's mouths into the basin below.

The Church of Santa Maria ai Monti (or Madonna dei Monti) extends along Via dei Serpenti. Often forgotten by the Romans, it is actually the heir to an extraordinary history. It stands where a 13th-century Poor Clare monastery once stood. At the time, one room was decorated with a fresco of the Madonna and Child with Saints, but after the nuns left, the premises were used as homes and barns.

The turning point came in April 1579: the building was shaken by vibrations similar to an earthquake. It is said that a voice, coming from a cavity in the wall where the ancient fresco was hidden, begged not to hit the Child. The news spread quickly, attracting crowds and leading to numerous miraculous healings. Pope Gregory XIII then commissioned Giacomo della Porta—already engaged in the completion of the Church of the Gesù—to build a new church to house the sacred image. Santa Maria ai Monti thus became the second church of the Jesuit Order in Rome.

The square also features the small, ancient Ukrainian-Byzantine rite church dedicated to Saints Sergius and Bacchus, martyred in Syria in 303 under Diocletian. The origins of this place of worship date back to the 9th century, during the pontificate of Leo III. The church is also known as "Madonna del Pascolo" (Our Lady of the Pasture) following the discovery in 1718 of a Marian image under the plaster of the sacristy (later moved to the high altar in 1730).

The current building was rebuilt in 1741 by Francesco Ferrari. The neoclassical façade from 1896 retains a 17th-century travertine portal surmounted by an inscription commemorating the restoration commissioned by Cardinal Antonio Barberini. The interior, with a single nave and barrel vault, boasts an 18th-century fresco by Sebastiano Ceccaroni. The high altar, by Filippo Barigioni, is embellished with antique green columns and houses the venerated image of the Madonna del Pascolo.