Attorney Caffrey grew up in Lawrence, Massachusetts, attending the public grammar schools there. He then attended Brooks School. Attorney Caffrey earned his undergraduate degree at Dartmouth College, and his JD at Villanova University School of Law.

Caffrey & Caffrey opened its doors in 1977, with Attorney Caffrey and his father practicing together until 1996. Since then Andy has been a solo practitioner.

Attorney Caffrey has been involved in many civic organizations and boards:
  • Member, Real Estate Bar Association
  • Member, Massachusetts Bar Association
  • Member, Greater Lawrence Bar Association (Past President)
Brooks School and Dartmouth College, Alumni Boards
  • Norman Williams Public Library, Woodstock, Vermont - Board of Trustees
  • Andover Chamber of Commerce - Past Board Member, Past President
  • Andover Community Trust - Current Counsel, Past Board Member
  • A.V.I.S. - Current Counsel
  • Andover Historical Society - Past Board Member
  • American Red Cross, Merrimack Valley Chapter - Past Board Member