The etymological meaning of "Hilandar" is probably derived from the Greek word chelandion, which is a type of Byzantine transport ship, whose skipper was called "helandaris".

As Hilandar's founder, Saint Symeon issued a special founding charter or chrysobulls, which survived until World War II, when it was destroyed as a result of the Operation Punishment and the notorious April 6, 1941 Nazi Germany bombing of Belgrade that leveled to the ground the National Library of Serbia building in Kosancicev Venac.

[15] Following the relocation of Saint Symeon's remains, what would eventually become world-famous grapevines began growing on the spot of his old tomb, which gives to this day miraculous grapes and seeds that are shipped all over as a form of blessing to childless married couples.

Saint Sabbas the Sanctified adjured his monks centuries earlier to donate the icon of the Milk-feeding Theotokos and his hegumen cane to the "namesake monk of royal blood from a faraway land" who would experience, during his pilgrimage to the monastery, the fall of his hegumen cane to the floor, previously affixed above his grave, while venerating icons and praying on that spot.

In order to effectively deal with consequences of the Crusader Latin plunder, King Uroš the Great constructed a large fortification surrounding the monastery with the protective tower named after the Transfiguration of Christ.

In the early 14th century, pirate mercenaries of the Catalan Grand Company repeatedly raided the Holy Mountain, while looting and sacking numerous monasteries, stealing treasures and Christian relics, and terrorizing monks.

[21] Consequently, Serbian King Milutin played a major role in building the Hilandar monastery complex by reconstructing and expanding it.

[23][24] Milutin also added a new main entrance gate which a chapel dedicated to Saint Nicholas built in, in addition to the newly erected monastery dining chamber.

At that time the number of Serbian monks skyrocketed and monasticism flourished even further as Byzantine Emperor Andronikos II Palaiologos donated large pieces of land to the monastery's estate in Greece.

He also took his wife Empress Jelena with him, thus creating a precedent and violating the strict tradition of "avaton" that bars women from stepping into Mount Athos.

In memory of Emperor Dusan's visit, the Hilandar monks erected big cross and planted the "imperial olive tree" on the spot where they welcomed him.

Serbian Emperor also built the Church of St. Archangels and expanded the monastery's hospital around 1350, while Empress Jelena endowed the Karyes monastic cell dedicated to St. Sava which belongs to Hilandar.

In addition to Dusan's son Serbian Emperor Uros V, powerful noblemen also supported Hilandar, such as Prince Lazar Hrebeljanovic who constructed the narthex along the west side of the main Entry of the Lady Theotokos into the Temple Church in 1380.

Following the fall of the Serbian Despotate to the Ottoman Turks in 1459, Hilandar lost major guardians and benefactors as its brotherhood looked for support from other sources.

In March 1556, Tsar Ivan IV Vasilyevich, whose maternal grandmother Ana Jakšić was by birth member the Serbian Jakšić noble family and paternal great-great-grandmother Helena, Empress Consort of Byzantium was also Serbian, also granted the Hilandar Monastery a plot of land with all necessary buildings in Moscow within a short walking distance from the Kremlin.

[34] Ilarion Makariopolski, Sophronius of Vratsa and Matey Preobrazhenski had all lived there, and it was in this monastery that Saint Paisius of Hilendar began his revolutionary Slavonic-Bulgarian History.

The Holy Council of Mount Athos refused, and since then every monastery generates its own power, which is gained mostly from renewable energy sources.

Among the numerous relics and other holy objects treasured at the monastery is the Wonderworking Icon of the Theotokos "Of the Akathist", the feast day of which is celebrated on January 12.

The monastery also possesses the Wonderworking Icon of the Theotokos "Of the Three Hands" (Greek: Tricherusa, Serbian: Тројеручицa), traditionally associated with a miraculous healing of St. John Damascene.