According to The Primary Chronicle, Presbyter Hilarion (whom Prince Yaroslav later appointed Metropolitan of Rus) dug a small cave near the village of Berestove, and in 1051 the monk Anthony, having returned from a pilgrimage to Athos, chose a cave on the same hill instead of one of the Kyiv monasteries. Other monks joined him, and so the monastery emerged to life. It is a common opinion that the monasticism in Rus was initiated by the abbot of the Kyiv-Pechersk Monastery Theodosius, because he adopted the Studite Statute regulating the life and activities of monasteries. Subsequently, the statute was adopted by all the monasteries of Kyiv Rus.
In 1169, the monastery received the title of Lavra, and already in the 13th century a corpus of texts about Lavra monks and ascetics was compiled in The Kyiv-Pechersk Patericon. The Lavra was also an important cultural center: it housed the first hospital in Rus, an icon-painting workshop, a printing house had existed there since 1615, and in 1630 Metropolitan Petro Mohyla founded a school.
The ensemble of the Kyiv-Pechersk Lavra is extremely picturesque, and the view of it from the Dnipro has always been counted among the best Kyiv panoramas. The dominant feature of the ensemble is the Great Lavra belfry towering above the entire complex of monastery buildings as it reaches 96 m 52 cm in height. It was built in 1731–1745 per the design of the architect Johann Gottfried Schädel. Signing the receipt of the fee, Schädel added in German: ‘You, oh majestic creation, built by my imagination and energy, will be solemnly greeted by descendants.’ The bell tower has four tiers with excellent decoration of the columns on each level. On the first tier there was an archive, on the second a library, on the third bells, on the fourth the clockwork.
The primary church of the Lavra is the Dormition Cathedral, consecrated in 1089. It was built in imitation of Byzantine models, and Alipii of Pechersk, the first Rus icon painter whose name had been preserved, took part in the painting work. The cathedral was repeatedly rebuilt and renovated, in particular in the 17th century, under Hetmans Ivan Samoilovych and Ivan Mazepa. In 1722–1729, the Dormition Cathedral was decorated with stucco and frescoes, and a magnificent five-tiered iconostasis was erected.
In 1920, the Kyiv-Pechersk Monastery was closed, and the monastic had been confiscated as possessions declared the property of the people. In 1922, the Museum of Cults and Daily Life was established here, it saved the complex from destruction, and in 1926 the authorities declared the Lavra a historical and cultural conservancy area, and the All-Ukrainian Museum Town was organized here.
During the World War II and the Nazi occupation of the city, the Dormition Cathedral was blown up – probably, the Nazi detonated an explosive, which was laid before the retreat of Soviet troops. In 1998–2000, the cathedral was restored in Baroque forms of the second half of the 18th century.