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Background: This study examines the management and outcomes of large paranasal sinus osteomas (PSO), especially those abutting or encasing critical structures of the skull base and orbit., Methodology: A multicentric retrospective analysis was conducted between June 2007 and September 2023. The study included surgically treated (regardless the type of approach chosen) PSO, exceeding 3 cm in diameter and/or located in critical anatomical areas. An analysis was performed to assess the association between the critical relationships, size, presence of residual disease, and incidence of intra- and postoperative complications., Results: The series included 160 patients. Most PSO were diagnosed due to clinical symptoms, predominantly for those located in the frontal sinus. Residual disease was observed in 9.4% of patients, with its occurrence influenced by PSO size and relationships with specific anatomical structures. Thirty-five/160 (21.9%) of patients experienced one or more intra- and/or postoperative complications. Intraoperative complications were associated with the proximity of PSO to the cribriform plate. Long-term complications were more frequently observed in cases involving the anterior and posterior plate of the frontal bone., Conclusions: This study highlights the complexities involved in managing large PSO, demonstrating that size and anatomical relationships of these osteomas can critically influence surgical decisions, residual disease, and complication rate. The study's retrospective design limited the collection of standardized symptom outcomes, highlighting the need for future studies to address this apect.