The most important benefactor of Chilandar monastery was Serbian King Milutin (1282-1321), exposing Serbia to stronger Byzantine social and cultural influence by incursions into Byzantine territory in Macedonia. He in 1293, built a new main church on the foundations of the old one, extending existing fortifications; in 1302 he built Hrusija by the harbour and so-called Milutin's Tower.

At the end of the 14^th century and in early 15^th century, during Serbian princes and despots, the Chilandar's property continued to expand. Prince Lazar (1371-1389) added to the main Chilandar church so-called Lazar's narthex. It was before the Battle of Kosovo.

TZAR DUSHAN’S CROSS Halfway between the sea and Chilandar stands a cross-like sign. It was erected by Tzar Dushan the Mighty on the very place where he was met by the Chilandar community. Carrying icons and relics, the Chilandar monks greeted him with bread and salt. It happened in 1347 when the Tzar took refuge with his family and train on Mount Athos, fleeing from the epidemic of plague in Serbia.

Karyes, the building of the Holy Community      
and bell-tower of the Protaton.

Chilandar, the main church, a baroque pyrgos (18th century), and the pyrgos of St. George, view of the southern side of the Monastery courtyard.

KONAK - MONASTIC QUARTERS According to the Athonite and Byzantine
rules, all monastic quarters were built within the enclosure walls. Old Chilandar
monastic quarters have not been preserved. The present-day quarters date from the period between the late 16^th and the late 17^th centuries. The legend has it that some of the distinguished Chilandar people lived in those cells. The cells of the Old Symeon and Monk Sava are in the small residence building near the well. On the first floor of the residence building near the Church of the Virgin’s Shroud is the cell of Paisios of Chilandar, "the father of the Bulgarian
history".

The western part of the residential building added in the 19th century. This period saw the last major architectural undertakings, all springing from the medieval nucleus, so that there are no marked transitions between the various architectural strata.

The eastern part of the Monastery with pyrgos of St. Sava, parekklesion of St. Archangel and the new library.

KING MILUTIN’S TOWER On the road leading to the Chilandar monastery, in a place close to the sea called Sava’s field, King Milutin erected a defense tower at the beginning of the 14^th century. It was called after him "King Milutin’s Tower" and is still well preserved. Being over forty meters tall, it is the highest building on Mount Athos. It has a rectangular ground plan and consists of ground floor and five stories connected by a spiral masonry staircase.

According to the Holy Mountain tradition, there was a paraccleseion, a small chapel, at the top. The view from the top, both of the sea and land, was excellent, so the monastery could be advised of danger in good time. It was in this tower that Empress Helen, consort of Dushan the Mighty, stayed at the time of plague epidemic in Serbia, in 1347. In order to prevent a woman’s foot to touch the sacred ground, the Empress was carried in a sedan chair from the port to the tower.

Chilandar under Turkish occupation

The first Turkish occupation of the Holy Athos occurred in 1387, and 1393-1403, and finally in 1430. The Ottoman Empire sanctioned the autonomous organization of the Holy Athos, but it lost many of its estates and revenues outside peninsula, and was burdened by taxes. So it happened to Chilandar monastery, too.

In 16^th century the czars helped Chilandar allowing its monks to collect contributions in Russia. During the 16^th and 17^th century and later an important source of income for Chilandar monastery was contributions from devoted Christians throughout the Balkans. On the other hand, Serbian patriarchs, bishops and clergy continued to assist Chilandar.

During the Greek uprising 1821, the Turks introduced severe reprisals and imposition of 10 year occupation, when a large number of monks had fled from the Holy Athos. Many antiquities and art treasures were destroyed.

But, beside of many tragic events throughout its history after the Nemanjic's period, the Chilandar library today contains about 1000 Slavonic manuscripts and nearly 180 Greek codex and booklets from 12^th to 19^th century; a collection of 80 copies of old Serbian and Wallachian printed books, and excellent specimens of Cetinje icanubula. There are also copies of almost all works of monastery's manuscripts and medieval Serbian literature (12^th to 17^th centuries) both originals and translated from Greek. This makes the richest treasury of old Serbian literature and manuscripts. There are also Bulgarian, Macedonian, Russian, and Slavonic works from Romania. Today's Chilandar library reflects and confines the international ecumenical character of the Holy Athos monastic community "which has unified the culture of all the Orthodox nations from the Middle Ages through the Turkish period down to the present day."