Katie Hefferon Headshot

Kathryn O’Leary Hefferon


Following in her father’s footsteps, Kathryn (Katie) O’Leary Hefferon marks the fourth generation of O’Leary Law. An alumnus of Suffolk University Law School as well, Katie utilizes her legal expertise to uphold the O’Leary family value of being in service to your community. 

Katie is a highly organized and personable attorney with nearly seven years of experience in general practice handling matters in a variety of Massachusetts Courts, including District, Superior, Housing and Probate Courts.

Bar Admissions

  • Commonwealth of Massachusetts


The O’Leary Law Firm, Winchester, MA

Associate, November 2015 – Present

Paralegal, August 2014 – November 2015

Office of the Bar Counsel, Boston, MA

Law Clerk, May 2013 – May 2014

Suffolk County District Attorney’s Office, Boston, MA 

Victim Witness Advocate, March 2011 – August 2012

Essex County District Attorney’s Office, Salem, MA

Victim Witness Advocate, June 2008 – March 2011


Suffolk University Law School, Boston, MA

Juris Doctor, January 2014

Clark University, Worcester, MA

Bachelor of Arts in American Government with a concentration in Law and Society, May 2008

Community Experience

Winchester Rotary Club, Winchester, MA 

June 2018 – Present

Horizons for Homeless Children, Roxbury, MA

Playspace Activity Leader, May 2015 – November 2017