It is believed that intially, the Kilifarevo monastery was built between 1348 and 1350. Its founder is the renowned Bulgarian clergyman, Teodosii of Turnovo, who with the help of the then-ruler, Tsar Ivan Alexander, transformed the cloister into one of the most important centres of the Bulgarian education and literature of the Middle Ages. A Kilifarevo school of literature was established for a short period of time and in 1360, this was already teaching 460 students, the most famous of which was the future Bulgarian Patriarch, Evtimii of Turnovo.

The monastery was surrounded by thick fortified walls, while the monks’ residential part was placed in their inward-looking side. A few-storey tower was rising in the centre of the inner yard, offering a good sight over the road to the Haimboaz Pass. Its existence, however, did not save the Kilifarevo fortress from being ruined to the ground and the large-scale cutural centre – from being completely destroyed shortly after the invasion of the Ottoman troops in Bulgaria. Centuries afterwards, in 1718, the monastery was restored in its present-day place. In the end of the 18th century the cloister was raided and destroyed by the so-called Kurdzhalii several times, but only to be rebuilt again and again.

Following years-long appeals before the Turkish authorities and fund-raising campaigns, the famous Bulgarian Renaissance master, Kolyo Fitcheto, started the construction of the present-day one-dome basilica St Dimitar in 1840. The master decided to preserve the old altar wall and the two chapels, dedicated to St Teodosii and St Ivan of Rila. The church was finished in 1842, while the internal decoration was completed a year later. The iconostasis represents a golden masterpiece, done by two woodcarvers, Tsonyo and Simeon Vassilevi – a father and a son from the town of Tryavna. Bsides the ocnostasis, the visitor is also impressed by the icons of the Tryavna iconpainters Dosyu Koev, Simeon Simeonov, Yonko Popvitanov.

In addition to the church, currently the complex also includes two beautiful residential buildings in authentic Renaissance style, the older of which dates back to 1849. The monastery is declared a monument of culture.