[3] The new monastic complex known today was founded in 1341 by Despotes Jovan Oliver Grčinić, a magnate of Serbian kingdom who owned the surrounding area.

Jovan Oliver built a church dedicated to St Michael as well as new dwellings and bestowed a charter to Lesnovo in which he lists its numerous possessions.

In the Serbian state assembly held in Skopje in 1347 Emperor Dušan pronounced Lesnovo monastery as the seat of the newly established Zletovo bishopric.

In 1381, the local lord Konstantin Dejanović issued a third charter giving Lesnovo back to Chilandar and placing it under the supervision of the bishop of Velbužd, his capital.

The reconstruction undertaken by its abbot Neofit in that year opened a series of works by the rich people from the nearby mining town of Kratovo that at the time flourished itself.

[7] After the defeat of a local uprising in support of the advancing Habsburg army the monks had to flee Lesnovo and the monastery was looted.

In 19th century Lesnovo got famous for a number of valuable manuscripts that were sold by monks and that have reached many libraries (Belgrade, Sofia, St Petersburg...).

Its architecture follows Byzantine cannons with alternate layers of brick and stone and decorative arches in two levels (similar to the Church of St Michael in Štip).

[8] The narthex, since it was built only a few years later (1347) forms a harmonious whole with same decoration of walls, a smaller dome above it and three double bay entrances.

As depictions of king David's psalms there are interesting compositions of sun, moon and twelve zodiacal signs, a round dance to drums and cither and several other scenes from 14th-century life.

Next to his portrait is a longer inscription that lists his rise to position as one of the most powerful lords of Serbia – significant for the grading of baron's titles.

The large wooden iconostasis was done in 1811–14 by Petre Filipović and his band (tajfa) of woodcarvers from the Mijak clan in West Macedonia.

In it is the bell cast in 1860 in Kragujevac and bears an inscription that it presents the donation of Prince Mihailo Obrenović of Serbia.