Dr. Calabrese received his Doctor of Dental Medicine degree and Certificate of Advanced Graduate Study in General Dentistry from the Boston University Henry M. Goldman School of Dental Medicine in 1991 and 1992, respectively. He then completed a US Department of Health and Human Services / Bureau of Health Professions Faculty Training Fellowship in Geriatric Dentistry at the Boston Medical Center / Boston University Henry M. Goldman School of Medicine in 1994.

Dr. Calabrese joined the faculty of the Boston University Henry M. Goldman School of Dental Medicine (GSDM) as a Course Lecturer in 1992. He was appointed Assistant Professor in the Department of Restorative Sciences and Biomaterials in 1994, Assistant Professor in the Department of General Dentistry in 2001, and Clinical Associate Professor in the Department of General Dentistry in 2014. In addition, Dr. Calabrese was appointed as a Clinical Instructor at Harvard School of Dental Medicine and has been a guest lecturer at the Massachusetts College of Pharmacy and Health Sciences Forsyth Dental Hygiene Program as well as the Mount Ida Dental Hygiene Program.

Dr. Calabrese currently serves as the Associate Dean of Students, Director of the Geriatric Dental Medicine Program, Deputy Title IX Coordinator and a Director of several academic courses at GSDM. He is the Director of Dental Medicine and an attending dentist at Hebrew Senior Life in Roslindale and Dedham, MA.