Legal 02

Atty. Robert D. O'Leary

December 1, 1923 ~ August 1, 2019 (age 95)


Attorney Robert D. O'Leary of  Milton passed away peacefully August 1, 2019. He was the beloved husband of the late Mary L. (Driscoll) O'Leary as well as the devoted father of Robert D. O’Leary, Jr. & his wife, Mary Ellen of No. Easton and Beth Hommes  & her husband, Bill of Hilton Head, SC and cherished grandfather of Catherine L. Becker of Stoneham, Christine E. Hommes of NY, NY, Robert D., O'Leary III of So. Boston, James M. O'Leary of Santa Monica, CA and Brian P. O’Leary of NY, NY. Great grandfather of Sara Becker, Leila, Hailey, and Chase O’Leary.

Bob grew up on Franklin Street in Milton.  He had a wonderful childhood and loved telling stories about adventures with his family and friends.  His education at Boston College was interrupted by World War II.  He served in the army in France in the engineering corps. When he returned from the war he finished his undergraduate degree at BC and enrolled in BC Law.  After graduation he met Mary Driscoll to whom he was married for 64 years. They returned to Milton to raise their family. He loved Milton, St. Elizabeth’s, his neighbors, BC football, the Red Sox and most of all his family. His law practice and Town Counsel obligations kept his busy but he always found time to attend his son’s and later his grandsons’ athletic events. He especially enjoyed their baseball games on warm spring days.  For thirty years he kept boats on Boston Harbor. He spent many weekends cruising within the harbor islands and around the Cape. His children and grandchildren joined him for many of these outings.  His greatest joy was holiday family dinners which grew larger as four great grandchildren joined the fold.

He lived his life by two adages,”  To whom much is given much is expected”,  and “ Nothing easily obtained is ever highly valued”.  Family members enjoyed his counsel and sought his advice throughout his life.  He will be greatly missed.

Funeral Mass at St. Elizabeth Church, Milton, Tuesday August 6, 2019 at 10 am. Visiting hours at the Alfred D. Thomas Funeral Home, 326 Granite Ave., Milton, Monday, August 5, 2019 from 4 to 7 PM. Burial will follow in Milton Cemetery. Attorney O'Leary was a graduate of Boston College and Boston College Law School. He was the former Town Counsel for the Town of Milton. In lieu of flowers expressions of sympathy may be made to St. Elizabeth Church, 350 Reedsdale Rd., Milton, MA 02186. 

To send flowers to Atty. Robert D. O'Leary's family, please visit our floral section.

 Service Program


August 5, 2019

4:00 PM

August 6, 2019

10:00 AM

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