Aims: The aim of this retrospective study is to evaluate the role of pulmonary metastasectomy (PM) in patients affected by lung metastasis (LM) of grade 2 and 3 chondrosarcoma (CS). Patients and Methods: The study included 61 patients affected by LM. Patients unfit for PM were treated with chemotherapy and radiotherapy. Results: The patients’ mean age was 51 years, ranging from 17 to 84 years; 44 (66.7%) patients had grade 2 CS, while 17 (25.8%) patients had grade 3 CS. Fifty-one patients presented multiple nodules: 44 of those cases were bilateral LM (72.1%). Twenty-nine (47.5%) patients underwent PM, whereas 32 (52.5%) patients underwent chemotherapy and stereotactic radiotherapy alone. At the final follow-up (average of 83 months, range 13–298), 47 (77.0%) patients had died of the disease. A better post-relapse survival rate was observed in patients who underwent PM (55.1 vs. 13.1% at 5-year follow-up, p < 0.001) and in patients with unilateral LM (60.4 vs. 25.6% at 5-year follow-up, p = 0.016). The number of LM also played a prognostic role. Conclusions: Until significant improvements in chemotherapy can be made, PM can be a valid option in the attempt to improve post-metastatic survival.