Breast angiosarcomas are rare mesenchymal tumors of vascular endothelial origin, most commonly associated with radiation, and less frequently primary. They are characterized by a distinct clinical and radiological presentation, frequent local recurrence, and a poor prognosis. We report the case of a young patient who presented with primary angiosarcoma in both breasts, occurring a year apart. Subsequently, she developed bilateral ovarian metastases, treated with surgery and radiotherapy for breast tumors, and underwent palliative chemotherapy for ovarian metastases. Diagnostic challenges were encountered in both radiological and pathological aspects. Through this case, we discuss the clinical, radiological, and pathological features of asynchronous bilateral primary angiosarcoma of the breast with ovarian metastases.