The icon of Theotokos Herondissa surrounded by a wooden frame is placed on the north wall of the Katholikon of the Philotheou Holy Monastery, near the north entrance. It belonged to an old metochion of the monastery, which was located in Nigrita near the town of Serres.
The icon depicts the Virgin Mary holding Jesus Christ in her left hand, while He is blessing and carrying a closed scroll. The inscription on the icon states: "Mother of God, the Merciful." and "Jesus Christ". As far as its iconographic type is concerned, the icon belongs to a modified version of Theotokos Hodegetria, as the Virgin does not raise her right hand, but holds Jesus' left foot with it. This detail is noticed by the beginning of the 13th century in a Cypriot work, now kept in the Museum of Byzantine Art in Athens. According to research, the icon of Theotokos Herondissa is associated with the Passion awaiting the Divine Infant in the future. It is worth noting that from its stylistic features and iconography, the icon is considered to be part of a series of individual works of the Palaiologan era. Among them there are placed Theotokos of the Xenophontos Holy Monastery (early 13th century), Theotokos of the Holy Monastery of Saint Paul (late 13th - early 14th century), as well as an icon of the Municipal Art Gallery of Thessaloniki (early 14th century). However, its technical characteristics and stylistic elements link it to the Cretan school of the 16th century. It is therefore dated to a later period, in the second third of the 16th century.
