The monastery church was built before the 15th century and painted in 1597; some of those frescoes are preserved. In 1611, the south facade was painted. The Rozhen Monastery was devastated by fire between 1662 and 1674, destroying the library and severely damaging most buildings. The monastery was restored over the next century with the financial help of rich Bulgarians from the whole country. The reconstruction began in 1715 and was fully finished in 1732.

The monastery reached its apogee in the 19th century, when it was a regional centre of Orthodox Christianity and owned a lot of land in the area. Famous Bulgarian revolutionary Yane Sandanski’s grave is located near the monastery.