Foot is an unusual site for chondrosarcoma and involvement of phalanges is extremely rare. We report a case of grade 2 chondrosarcoma of proximal phalanx resulting in its fracture along with transarticular extension to the middle phalanx of the 2(nd) toe of right foot in a 62 year old female. The patient presented with 1 and (1/2) year history of pain and swelling in right 2(nd) toe. X-ray showed presence of expanding lytic lesion with amorphous calcification along with fracture proximal phalanx. Fine needle aspiration cytology showed some pleomorphs, osteoclasts and some giant cells. We went for amputation of toe without a biopsy. Histopathological examination of specimen showed multiple pleomorphic cells, nuclear atypia, hyperchromasia with some giant cells (grade 2 chondrosarcoma).