William Burke O’Leary

Over 30 years of experience working for you

About William Burke O’Leary

With over thirty years of experience, William O’Leary has been in private practice since 1983. He is an alumni of Suffolk University Law School in Boston, Massachusetts, where he received his Juris Doctor degree and the University of Massachusetts where he earned his Bachelor of Arts in Political Science. Bill has a broad spectrum of experience and skills in civil litigation, administrative municipal, real estate, commercial, workers’ compensation, admiralty, criminal and probate law. He has appeared before the superior and district courts in Massachusetts, the Industrial Accident Board, the United States District Court for the District of Massachusetts and other boards and agencies throughout the Commonwealth. He has developed a diverse group of professional colleagues and often takes the lead in managing complex legal disputes involving multiple parties.


O’Leary & Sbarra, Winchester, MA

Attorney at Law.  General practice law firm.  Engaged in the private practice of law since 1983.  Concentrating in civil litigation and administrative, municipal, real estate, commercial, workers compensation, admiralty, criminal and probate law.  Appear before Superior Courts, District Courts, the Industrial Accident Board, Board of Appeals, U.S. District Court.


United States Coast Guard, Boston, MA


Assistant District Legal Officer, 1979 – 1983.

Assistant Regional Counsel for federal maritime, regulatory and criminal law enforcement agency representing Maine, New Hampshire, Massachusetts, Rhode Island and Vermont.  Experience with maritime, labor, criminal, military justice, fisheries, environmental law.  Office of Personnel Management Procedures Course.


Military Magistrate


Summary Court Martial Judge


Data General Corporation, Westborough, MA


Associate Credit Analyst, 1976 – 1977.



Selectman, Town of Winchester, 1989 – 1998

Five member board in a town with a population of 20,500.  Town manager form of government, representative Town Meeting.  Served as Chairman for two years and Vice Chairman for three years.  Key player on a strong, active board.  Selectmen’s representative charged with negotiating with police superior officers, police patrolmen, NAGE clerical union, firefighters and Department of Public Works.  Accomplishments include litigation control, land use, labor issues, budget, housing, solid waste and personnel issues.  Served as Hearing Officer for labor appeals.  Also served as Town Meeting Member, 1989 – 2000 and member of the Lincoln School Swing Space Committee, 1999.


Candidate for State Representative, 34th Middlesex District, including Winchester, Stoneham and Reading, 1988 and 1998.



Suffolk University Law School, Boston, MA

Juris Doctor, June 1979.  Phi Delta Phi Society, Suffolk Transnational Law Journal - Staff Member, Director, Suffolk University Law School Alumni Association, 1984 – 1987, Outstanding Fund Raiser Award, 1983.


University of Massachusetts – Dartmouth, North Dartmouth, MA

Bachelor of Arts, Political Science, 1976, with highest honors.



United States Coast Guard Reserve, 1969 – 1975

E-4 BM3, Honorable Discharge.  Active Duty, 2 years, Coxswain of Search and Rescue Boat 44398, Station Brant Point, Nantucket, MA.



Married to Cheryl Sbarra O’Leary, Esquire, two children - Katie, 29 and Burke, 24.  Winchester resident since 1981.  Volunteer activities include youth sports, Winchester Cooperative Theatre for Children, and youth music