Orbital chondrosarcoma arising from paranasal sinuses or from the nasal cavity with orbital extension is highly unusual. The aim of this report is to describe our multidisciplinary experience in the treatment of three patients with extensive sino-orbital chondrosarcomas. The patients were aged 43, 75 and 63 years, and the tumors originated from the maxillary, sphenoidal, and ethmoidal sinuses, respectively. Magnetic resonance imaging studies showed homogeneously hypointense lesions on T1-weighted scans, which were hyperintense on T2-weighted images. Intranasal endoscopic surgery alone or in combination with other conventional surgical approaches was the main therapeutic choice. Two patients had recurrences treated with wider surgical removal. Fractionated stereotactic radiotherapy was used in two cases. Two patients had histopathological grade I tumor and one had grade III chondrosarcoma. No patient had regional spread or distant metastasis. All patients were disease-free at 4, 2, and 3 years, respectively, following their last therapeutic interventions. Endoscopic surgery results in lesser morbidity for chondrosarcomas arising from paranasal sinuses and extending into posterior parts of the orbit. However, because control of surgical margins may not be complete, recurrences may occur justifying more radical approaches.