It is deduced from written monuments the progenitor of Hrabren-Miloradović family was probably chieftain from Donji Vlasi, Milorad Hrabren, who lived in the second half of 14th century. In 1416 is mentioned his son, Stipan, in appeal by Republic of Ragusa due to fighting along Petar Pavlović, a magnate of the Kingdom of Bosnia against Sandalj Hranić and Ottomans in the Lower Neretva near Slivno. He had three sons: Petar Stjepanović is first mentioned in 1473 and last time in 1486, Radoja Stjepanović died between 1475–1477, while Vukić Stjepanović was mentioned for last time in 1496. They had lands between Stolac and Mostar. Members have been buried at Radimlja near Stolac, which was in their possession. Radimlja was most likely the clan's graveyard. There are epitaphs on five medieval stećci referring to the Miloradović family.
Ottoman period
During the Ottoman period, some members of the family were Christian sipahis. As Ottoman subjects, they were given privileges and possessions, where they founded churches. The various family members in various times erected four of such buildings: the Church of Peter and Paul in Ošanići was built prior to 1505, its founder was duke Radoslav, the Church of St. Nicholas in Trijebanjj, 15 km from the town of Stolac, is erected in 1534 as an endowment of duke Radoje Hrabren, in Klepci the Church of the Transfiguration of Christ, built by sipahi Milisav Hrabren-Miloradović most likely close to the end of the 16th century, and the Žitomislić monastery 1566 by duke Petar and his brother Ivan. The katun formation by Petar and Vukić Hrabren was part of the Vlach group Donji Vlasi of nahiye Blagaj - and their katun was the largest with 127 houses and 16 unmarried persons out of 37 katuns, 1383 houses and 177 unmarried persons. At the time Petar Stjepanovič-Hrabren along knezes Vukac, Pavko, Stipan and Radivoj Popratović was included in the order of Ragusan citizens, as well was Ottoman timariot. When the Ottoman feudal system, which they were part of, started falling apart in Herzegovina in the 16th and 17th centuries, the clan started dispersing itself as they felt unsafe. The Miloradovići in Dubrava remained in Ottoman service as sipahi with the Sultan's grant until the mid-17th century, when more Ottomanized nobility which had the ruling power pushed them aside. Those members of Miloradović-Stjepanović who remained in Žitomislić have taken collective surname Ljoljić and Kuzman, while those who converted to Islam have taken surname Opijač and today live in Dubrava near Stolac. From the Dubrava family, Jeronim Miloradović-Hrabren became an Austrian officer in the 18th century.
Miloradovich family in the Russian Empire
Since the 17th century some Miloradović members migrated to Russia, with occasional visits to Herzegovina carrying gifts and Church books. Mihailo Miloradović and Metropolitan Danilo I Petrović-Njegoš had been recruited by Peter I of Russia to incite rebellion in Herzegovina against the Ottomans in 1710–11, but after unsuccessful attempts Mihailo was forced to flee Herzegovina to Little Russia where he joined Peter's service as a colonel. Among Mihailo's descendants and prominent members of this branch include his grandson Andrei Miloradovich, a governor, and most importantly Mikhail Miloradovich, a Russian general prominent during the Napoleonic Wars. Count Grigorije Miloradović-Hrabren, a Russian colonel, visited manastir Žitomislić in 1883.
Legacy
Most important cultural and religious legacy of Hrabren-Miloradović are Radimlja family cemetery near Stolac, three churches, church in Klepci the end of the 16th century, 1505 church in Ošanići, 1534 church in Trijebanj, and the monastery from the second half of the 16th and the beginning of the 17th century in Žitomislić. Family members who emigrated to Russia rose to prominence, as high-ranking Imperial army officials.