We report a rare case of pleomorphic adenoma (benign mixed tumor) of the breast in a 66-year-old female. A 5.5 cm hypoechoic mass with lobulated margins was noted on ultrasound. A biopsy showed an atypical cartilaginous lesion, leading to a subsequent segmental mastectomy, which was initially interpreted as metaplastic breast carcinoma. On the second review at our tertiary care center, a diagnosis of a pleomorphic adenoma was favored due to the circumscription and the benign epithelial component. Due to unfamiliarity with this entity, this neoplasm has occasionally been misdiagnosed clinically and even been overcalled on core needle biopsies. Careful clinical, radiological, and pathological correlation is required to avoid unnecessarily aggressive surgery, and a differential diagnosis of pleomorphic adenoma must be included in cases of well-demarcated breast masses showing myxoid or cartilaginous changes on core-needle biopsy.