Chronic lymphedema (CL) due to failure of lymphatic drainage harbors an immunologically vulnerable environment for the development of various neoplasms. Independently, either melanoma or basal cell carcinoma (BCC) arising from CL has only been reported, but synchronous melanoma and BCC originating from CL is never reported. We report a very rare case of synchronous melanoma and BCC arising from the lymphedematous upper extremity developed secondary to axillary lymphadenectomy for breast cancer. Additionally, a literature review reporting either melanoma or BCC in the lymphedematous area was performed using Medline and PubMed databases.