Enchondroma is the most common benign cartilage bone tumor of the toes. In contrast, the foot is a rare region for chondrosarcoma, and the involvement of phalanges is extremely rare. In this article, we report an unusual case of intermediate chondrosarcoma involving the proximal phalanx of the great toe of a 52-year-old woman who was previously treated with curettage and bone grafting because of misinterpretation of enchondroma at a local hospital. She presented complaining of pain and swelling that she had experienced for a period of 1 year after the first operation. Radiography revealed a lytic lesion with a subtle punctuate calcification and endosteal scalloping in the proximal phalanx of the great toe. Gadolinium-enhanced magnetic resonance imaging confirmed soft-tissue involvement and cortical destruction. Staging evaluation with computed tomographic scan of the chest, abdomen, and pelvis was performed to ensure that there was no metastatic disease. Subsequently, a bone biopsy was performed, and the diagnosis was grade 2 chondrosarcoma. The patient was informed about the recurrence of the lesion and the clinical context on the basis of tumor biology of chondrosarcoma and was offered the option of either amputation or wide resection. She preferred the latter. The patient was treated with wide resection and underwent reconstruction with cement and Kirschner wire. She remains free of disease after 1 year of follow-up.