Desmoplastic fibroma (DF) is a rare non-metastatic yet infiltrating and destructive primary tumor of the bone. This fibrous benign lesion exhibits behavior similar to desmoid fibromatosis of soft tissues. It frequently affects young adults and long bones and is infrequently seen in the craniofacial region. Amongst jaws, mandible is most frequently involved. The present case series reports varied presentations of desmoplastic fibroma involving maxilla, a very rare location. The diverse clinical and radiographic features presented by the lesion have been elaborated along with its management.