Cholesterol granuloma is a histopathological finding characterized by a mass of connective tissue and granulation tissue. It is primarily observed in the middle ear, mastoid process, or paranasal sinuses, with rare occurrences in the dental odontogenic region. A dentigerous cyst encloses the crown of an unerupted tooth by expanding its follicle and attaches to the neck of the tooth. Here, we report a 63-year-old female who presented to the dental clinic complaining of an ill-fitted denture. A panoramic radiograph showed a well-defined radiolucent lesion in the upper left maxillary sinus with an impacted third molar. Computed tomography revealed loss of the anterior and lateral sinus walls. The cyst was enucleated surgically. The final diagnosis was confirmed by histopathological examination, which revealed focal areas of cholesterol clefts in the cystic wall of the dentigerous cyst.