Parapharyngeal space (PPS) masses are relatively rare lesions of the head and neck, and account for 0.5–1.5% of head and neck lesions. The most common lesion to occur in the PPS is a benign salivary neoplasm, typically pleomorphic adenoma either from the deep parotid or from ectopic parotid tissue rests within the PPS. A calcified or ossified mass in this location is exceedingly rare, but a calcified variant of pleomorphic adenoma has been reported. In this study, we present a patient with a heavily calcified PPS mesenchymal chondrosarcoma with an unusual presentation. We discuss the imaging and pathologic findings followed by a review of the current literature.