The cementifying fibroma is a benign fibro-osseous lesion. Its usual location is in the mandible while rare sites of involvement have been the maxilla and ectopic locations. These tumors are generally believed to originate from the connective tissue of the periodontal ligament. Clinically, lesions are usually asymptomatic, slow-growing, and well-circumscribed. However, in very few cases, particularly in younger patients, these tumors have demonstrated and apparent aggressive course of development. We describe a case of an aggressive cementifying fibroma of the maxilla in a middle-aged male. The pathogenesis of the tumor is discussed, and the need for appropriate surgical management is emphasized.