First mentioned in 1444, Mileševac Fortress is believed to have been erected during the reign of Stefan Vladislav in the early 13th century. It was strategically positioned along the road linking the cities of Prijepolje and Sjenica. The fortress served as a defensive stronghold guarding the nearby Mileševa Monastery, a significant Serbian spiritual centre and designated Monument of Culture of Exceptional Importance in Serbia since 1979. 

In 1465, the fortress fell to the Ottomans, whose records attest to the significance of the fortress. The Ottomans maintained a garrison within its walls for an extended period, and the fortress had become known as Hisarjik from the 17th century onward. The village where the fortress is located still held this name even after the Ottoman rule ceased, becoming Hisardžik in its legacy.

Perched upon a massive rock formation, the fortress enjoyed favorable defenses from all sides, thanks to the steep and impassable cliffs that surround it. The remains of the Mileševac Fortress still stands above the monastery as a symbol of Serbian medieval heritage.