The article examines Zinaida Serebriakova’s self-portrait At the Dressing Table (1909) through the lens of Sigmund Freud’s concept of the "uncanny," as introduced in his essay Das Unheimliche (1919). The study aims to identify abnormal elements within everyday life depicted in the artwork that subtly disrupt habitual perception and evoke a disoriented sense of an otherworldly reality. Freud's primary triggers of the uncanny, such as the repressed and the overcome, are outlined and explored in depth, focusing on themes like the "familiar becoming unfamiliar," the "feminine" as a source of the uncanny, and "animism", manifested through doublings, repetitions, reflections, and symmetry, referencing later 20th-century developments. Serebriakova’s self-portrait, traditionally seen as a cheerful domestic scene, acquires uncanny qualities when its focus shifts and new compositional relationships emerge. A peculiar loop appears to grow from the heroine’s head, an unusually positioned door handle marks a point of uncertainty, and the lower part of her figure seems fractured and punctuated by sharp lines. These elements together evoke the image of a mermaid, highlighting themes of the undead and the demise of femininity, imbuing them with a chthonic meaning. This context also suggests echoes of Venus, the goddess of love and femininity, appearing in both her luminous and dark aspects. Initially presented as a realistic artwork, the painting’s fantastical qualities surface upon closer examination, transcending the boundaries of reality—a characteristic central to the uncanny in art, as described by Freud. This study contributes to the art-historical and philosophical discourse on female self-portraits and deepens the understanding of the uncanny in visual art, offering new interpretations of familiar artistic themes and methods.