Saint Sylvester was born in Osimo, Italy, around 1177, into a noble family.

As a young man, Saint Sylvester was sent by his father to study at the Universities of Bologna and Padua, two of the most renowned centers of learning in medieval Italy. There, he studied civil law.

Saint Sylvester was appointed a Canon of the Cathedral of Osimo. He faithfully served the Church through prayer, preaching, and pastoral care.

Seeking a life of complete solitude, Saint Sylvester arrived at the remote cave of Grottafucile, far from the noise and distractions of the world. There he embraced a life of prayer, silence, fasting, and penance, desiring only to seek God.

As the number of his disciples continued to grow, the small hermitage at Grottafucile became too crowded. Seeking a place of greater solitude and prayer, Saint Sylvester led his followers to Montefano, a rugged mountain dedicated to God. There, he founded the Monastery of Montefano, the motherhouse of the Sylvestrine Benedictine Congregation. After a lifetime of prayer, service, and holiness, Saint Sylvester spent his final days at the Monastery of Montefano.

St. Sylvester was inspired by the life of Saint Bonfilius was an 11th-century bishop of Foligno who spent his final years as a hermit in the area. His first biographer, Sylvester established the community and dedicated it to San Bonfilius.