Prostate cancer metastases involving the orbit and/or paranasal sinuses represent a rare oncological presentation. Patients can have a myriad of symptoms such as proptosis, periorbital swelling, blurry vision, rhinorrhea, epistaxis, anosmia, or others depending on the structures involved. The differential diagnosis of paranasal sinus masses on imaging studies is broad and can include inflammatory, congenital, or neoplastic masses; leading to the requirement of biopsy for definitive diagnosis. Tissue sample is usually obtained via an endoscopic approach. The prognosis of such a presentation is not well described in the literature, but it is usually guarded due to the advanced stage of the disease and generally a poorly differentiated primary tumor. Treatments usually aim to reduce the burden of disease and debulk the tumor mass for palliative purposes. We present a case of a 71-year-old male presenting with unilateral proptosis and periorbital swelling secondary to prostatic metastasis.