The hamlet's origins are to be attributed to the ancient Picena civilisation who established a colony on the hill where the township rose around the VI century B.C..
In Roman times, these lands were crossed by an important road that linked Castrum Posoli in the Cervare di Montelupone area, to the major Roman cities of the zone, namely, Auximum, Potentia, Firmum. This arterial road allowed the settlement to grow in importance; confirmation can be found in the discovery of various Roman houses dotted around the most beautiful spots in the communal territory, as well as a temple to Apollo and various religious buildings. Even today there stands a great funerary stela marking the boundary between the Montelupone, Macerata and Morrovalle territories.
In 729 after the Longobard conquest, these lands were placed under the control of the Church and in particular were annexed to the possessions controlled by Bishop of Fermo.
Around the year one thousand, thanks to the magnanimity of a noblewoman from the house of Grimaldi, the “Pia Signora”, near the Potenza river the Benedictine abbey of St. Firmano was built, to which the feud of Montelupone was subject for a short period.
The positive influence of the Benedictine rule, “ora, lege et labora”, brought considerable benefit to the local population and laid the foundation for an era of great cultural development. The most ancient document bearing the name of the free commune of Montelupone dates back to 1150.
The local community must have boasted a good reputation as it was one of the communes in 1202 that sat beside Fermo and signed the treaty for the famous peace of Polverigi, between the same Fermo, Ancona and Recanati.
During this era, the lands were furrowed by daring commanders who took possession of the borgo. First in 1258 it was conquered by Percivalle Doria, Vicar of King Manfredi; successively, starting from 1294 first came Tebaldo Manetti followed by the Chiavellis.
In 1353, the commander Fra Moriale, helped by the German Luzzo di Lanzo, used the commune as his logistical base to plunder and pillage the neighbouring Marchigian centres.
In 1363 it was the turn of Pierfrancesco of Brancaleone, Lord of Casteldurante (Urbania) who was overthrown in 1407 by the dominion that the Malatesta family imposed on these lands, giving the go ahead to an important work of fortification.
Still today, the well preserved embrasures in the keeps of the urbic walls can be admired.
After a brief interval in which the borgo was subject to Braccio da Montone, the Malatestas held the reins of the city until 1433 when Francesco Sforza made his entrance and remained in power until 1447.
becoming part of the Church possessions and subject first to the Bishop of Pausola then to the Bishop of Fermo, thanks to the election of Pope Sisto V the city is inserted in the new diocese of Loreto where it spent a long period of tranquillity under the protection of the Holy Church.
In 1798, the year of the first suppression of religious orders and the confiscation of works of art by Napoleon's army after the treaty of Tolentino, Monteleone was honoured to give hospitality to the Recanatese family of Monaldo Leopardi (parents of the famous poet Giacomo Leopardi), fleeing from their own city.
The life of the borgo continued quietly until it was annexed with Marche to the Reign of Sardinia and to the successive unification of Italy in 1860. 

Monuments