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The original monastery church does not exist, which the King Milutin had demolished at the end of the 13th century in order to make a much larger edifice. But there are some signs that the original monastery church had carved ornamentation in the Byzantine style of that time. The interior with the gold of its frescoes left the strongest impression, which was recorded by Theodosius in his work of Life of St. Sava. The gold background for frescoes had a great influence on painting of the monastery churches in Serbia during the 13th and 14th centuries.
 The old iconostasis, composed of stone slabs rather than masonry, was small, like church. In some prominent place in the church, an icon of the Virgin Hodeghetria would be placed, as the Patron of Chilandar monastery, so that it can be properly venerated, since Chilandar monastery bore the Virgin's name from the time of its restoration by St. Simeon and St. Sava.
Throughout the 13th century, fresco and icon painting at Chilandar monastery was at the centre of the most progressive artistic trends in the Byzantine world and Serbian state, which accounts for the fact that Chilandar's works of art from that century are more numerous and even finer than those in other monasteries on Athos.
 After Milutin's reconstruction of Chilandar monastery, there had been no need to undertake any building. Over the next half century, the patronage of Serbian rulers mainly took the form of gifts of land.
From the imperial epoch, Chilandar has preserved some works which came into its possession much later, but it is a part of its history as weel. Most notable is the icon which receives the greatest veneration - the Virgin with the Three Hands (Trojerucica). According to the Holy tradition, the icon was brought to Europe from Jerusalem by St. Sava himself. But prior to this, the icon had shown its miraculous powers at the time of the iconoclast conflict by healing the hand of St. John of Damascus,  an opponent of Iconoclasm. In gratitude, he added an extra hand to the icon. This icon was particularly venerated in the capital of Serbian empire - Skopje, but after the conquest of Turks, it was miraculously transferred to the Chilandar monastery. It is a large processional icon, covered by silver and gold frames and ex-votos which conceal an Virgin and Child of the Hodeghetria type. The third hand is not painted but it is moulded in silver - added afterwards in accordance with the tradition.
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