Gorham-Stout syndrome is an extremely rare bone disorder characterized by osteolytic bony resorption. It is of unknown etiology and thought to result from localized endothelial proliferation of lymphatic vessels that cause the bony resorption. Diagnosis of Gorham-Stout can only be made after excluding other common causes of bony resorption such as those caused by infection, inflammation, malignancy, and endocrine. The clinical symptoms vary from minor pain and swelling to non-healing fractures from minor injuries. Due to the rarity of the disease, the overlap of symptoms with other diseases, and uncertain etiology, very few cases of Gorham-Stout syndrome have been reported. The disease is characterized by gradual resorption of bone particularly the bones of shoulder, skull, thorax, and spine, although long bones may also be affected. We present the case of a 45-year-old male patient who presented to the maxillofacial department with marked facial asymmetry leading to functional and aesthetic problems, showing massive osteolysis of both his mandibular condyles and majority of his ramus.