Inverted papilloma (IP) is a relatively rare neoplasm of the nasal cavity and paranasal sinuses. Although it is considered a benign tumor, its biological behavior is not so benign because of local aggressive growth, high recurrence rate, and risk of malignant transformation with associated carcinoma. Therefore, it requires complete surgical removal and long term postoperative follow-up. Bilateral IP is unusual and even more so when associated with simultaneous intra-orbital and intra-cranial extensions. These extremely aggressive behaviors have been separately reported in the literature, especially in recurrent cases. Report of cases with bilateral and multifocal involvement without malignancy has been exceptional. Surgical management in these cases includes an endonasal endoscopic approach combined with external approaches, either conventional or endoscopic minitrepanation. Intensity modulated radiation therapy can be useful in patients with incompletely resected disease. A case of this rare disease is reported.