Background Chondrosarcoma accounts for 20% of all bone sarcomas and may present with soft tissue extension. The presence of an extraosseous component, along with positive surgical margins, have been separately associated with increased risk of local recurrence and decreased survival. The purpose of this investigation is to describe the treatment and outcomes of 7 chondrosarcoma patients who presented with both chondrosarcoma with soft tissue extension as well as positive surgical margins post wide en bloc resection. Methods This was a retrospective review over a consecutive thirteen-year period. Data including treatment details and outcomes were included. All patients underwent attempted negative margin wide en bloc resection and encountered unplanned positive margins on intraoperative determination or post-operative pathology. Results A total of 7 cases were identified. Average age (SD) was 61.1 years (5.87) with median (range) follow-up of 17.0 months (3, 91). Four (57.1%) cases arose in the extremities, and 3 (42.9%) cases in the pelvis. All patients underwent attempted negative margin wide en bloc resection. Four (57.1%) cases recurred with median (IQR) time to recurrence 16.0 months (9.50, 22.0). At study conclusion, five (71.4%) were alive with median (IQR) survival of 23 months (12.5, 36). Overall survival (OS) probability was 100%, 53.3%, and 53.3% at 1, 3, and 5-years, respectively. Recurrence-free survival (RFS) was 60%, 40%, and 40% at 1-, 3-, and 5-years, respectively. Conclusion Despite a limited sample size, our data reflected similar OS to chondrosarcomas with positive margins alone, but a higher recurrence rate. Our cohort represents a high-risk subgroup of chondrosarcoma patients, which may dictate increased monitoring and guide future treatment recommendations for these patients.