The oldest religious building and one of the most important historical sites in São Paulo is the Monastery of St. Benedict (Mosteiro de São Bento). It is over 400 years old and it is still functioning. It is a residence for around 45 monks and it holds regular religious events. If you are lucky enough to be here at the right time, you can see or even participate in the daily service. Under the vaults of the monastery, those who need help or a confession are always ready to be taken care of.

The Catholic Monastery was founded in 1598, but the building that now decorates the center of São Paulo appeared only in 1922. It has been rebuilt at least four times. Originally it was a modest temple erected on the site of the house of Tibiriçá, a local tribal leader who was an ally of Portuguese colonists. The picturesque hill between the two rivers became an excellent place for a religious institution. Soon a small 4-cells monastery with a simple chapel appeared next to the temple.

In 1650, the building increased in size thanks to funding from one of the Bandeirantes. In gratitude, the monks allowed him and his family to be buried within the chapel. The remains of the famous emerald hunter Fernão Dias Pais and his family are still buried in the local crypt.

By the early 20th century, the monastery had opened Colégio de São Bento College, as well as the first philosophy university in Brazil and the first Benedictine abbey in Latin America. Monastery of St. Benedict became the country's foremost religious institution and needed to be expanded to meet its rapid development.

The reconstruction of the oldest monastery began in 1910 and lasted 12 years. The architect was Richard Berndl, professor at the University of Munich and one of Germany's best masters. The new building in neo-Romanesque style became one of the most beautiful in São Paulo. Today it is decorated with original stained-glass windows and carved wooden decoration brought by an architect from Germany. Above the main entrance, there is a clock with a mechanism of six bells, the ringing of which can be heard every hour. This clock is more than a century old and is considered to be the most accurate clock in São Paulo.

The monastery has the oldest library in the city, as well as a shop and a bakery with its own products.