A 79-year-old man presented with bilateral periorbital swelling of unknown duration. Diagnostic workup, including orbital and prostate biopsies processed with conventional hematoxylin-eosin and immunoperoxidase stains, revealed that the prostate was the origin of the orbital tumors. Our review of the literature revealed 17 previously reported cases of metastatic prostate carcinoma to the orbit. Salient clinical and histopathologic features of these cases are summarized. To the best of our knowledge, this is the first biopsy proven case of bilateral orbital metastasis of prostate carcinoma.