Osteoblastoma is a rare benign neoplasm of jaws. We report a case of a recurrent osteoblastoma in the maxilla of a 34-year-old male who presented with aggressive clinical and histologic features: namely root resorption, tooth mobility, involvement of maxillary sinus, chondroid formation, host bone trapping, and lack of osteoblastic rimming. The lesion is discussed with particular emphasis on its differentiation from malignant lesions especially low-grade osteosarcoma. A systematic review of other reported cases of osteoblastoma of jaws with a note on the recurrent cases has been put forth.