A 76-year-old man presented with slowly progressive swelling in his forehead and left upper eyelid over the course of three months. CT scanning showed non-specific enhancement of subcutaneous tissues, suggesting a low-grade cellulitis. Poor response to treatment prompted an MRI, which revealed the presence of a soft tissue lesion. Biopsy of this lesion was positive for angiosarcoma. The patient underwent chemotherapy and radiation, but unfortunately succumbed to his malignancy eight months later. This case illustrates a rare example of facial/periorbital angiosarcoma, a benign-appearing but aggressive tumor associated with a high incidence of mortality. A review of the literature and current treatment options are discussed.