Dentigerous cysts are benign odontogenic cysts associated with the crowns of unerupted, embedded, or impacted teeth. Most of them are associated with mandibular third molars, followed by maxillary third molars and canines. They are usually asymptomatic, and rarely do they grow extensively and compress the adjacent anatomic structures. We report 5 cases of extensive maxillary dentigerous cysts presenting with sinonasal and orbital symptoms. A literature review for similar presentations of dentigerous cysts has demonstrated 21 cases. Recognition of the extensive growth potential of the dentigerous cyst, diagnosing it with its unusual presentation, and appropriate management are discussed in this article.