Attorney Robert F. Dionisi, Jr.


Bob’s primary areas of practice are residential and commercial real estate. He represents buyers, sellers, developers, and investors in the acquisition, sale, permitting, and development of residential, commercial, and investment real estate. Bob is approved as closing attorney for most national mortgage lenders as well as local lenders, thrifts, and credit unions. Bob has conducted thousands of real estate transactions in the Commonwealth of Massachusetts from Barnstable County to Berkshire County with heavy concentration in the Metro-West Boston, Worcester, and Cape Cod areas. In addition, Bob co-manages the firm’s litigation practice which concentrates on Probate and Divorce litigation matters as well as civil litigation involving construction, business, and domestic disputes. Bob regularly counsels clients on estate planning and business strategies. Bob presently is outside counsel to two of the nation’s largest title insurance companies retained to resolve defective real estate titles in the Commonwealth of Massachusetts. 

Having formed a successful law firm with a wide range of practice, operating in the Greater Boston/Worcester areas for 28 years in which Bob represented major developers and investors in real estate through the Boston/Metro West Area. Bob founded Dionisi/O’Rourke, LLP in 2006 with his daughter Kristen L. O’Rourke, a former Assistant Attorney General for the Commonwealth of Massachusetts. Bob is proud to mention that his other daughter, Cara Bradford, a former attorney with the Department of Children and Families for the Commonwealth joined Dionisi/ O’Rourke, LLP and in 2013 became a partner in the newly named firm Dionisi, O’Rourke & Bradford, LLP. 

Educational Experience

Bob attended Cornell University, American International College, and Boston University School of Law. Bob has been active in Sudbury as a former member of the Town’s Planning Board and the Town’s youth sports programs over the years, and has acted as counsel to Christopher Haven at Boston’s Massachusetts General Hospital. Over the years Bob and his wife have been active in the Juvenile Diabetes Research Foundation on Cape Cod. He is an active member of the Oyster Harbors Club in Osterville on Cape Cod.


Bob is admitted to practice law in Massachusetts and before the U.S. District Court for the Districts of Massachusetts and New Jersey. He is a member of the Real Estate Bar Association of Massachusetts.


Sudbury Office
365 Boston Post Road, Suite 214
Sudbury, MA 01776

Osterville Office
PO Box 2090
Oyster Harbors,
Osterville, MA 02655