We present a case of an 18-year-old woman with recurrent bilateral giant fibroadenomas that were evaluated by mammography and sonography with color Doppler. Imaging revealed solid lobulated masses with significant internal vascularity occupying most of each breast; this evaluation suggested a differential diagnosis of giant fibroadenoma versus phyllodes tumor. The unusual clinical story of recurrent bilateral lesions as reported by the patient, coupled with the findings on visualization of these lesions by mammography and ultrasound with color Doppler, led to the clinical decision to forego biopsy in favor of immediate bilateral surgical enucleation.