Cover photo for Barbara O'Leary's Obituary
Barbara O'Leary Profile Photo

Barbara O'Leary

December 21, 1927 — December 16, 2022


Barbara O'Leary

Barbara K. O’Leary, age 94, of Winchester, passed away peacefully on December 16 at the Sawtelle Family Hospice House in Reading.

She was born in Boston on December 21, 1927 and was the daughter of the late Samuel and Jean (Clark) Kenton.

Barbara was the foundation of the extended O'Leary family. She was a fixture of her small Boston suburb, and everyone knew "Mrs. O" and her six boys.  Barbara was known for being a wonderful friend.  She had an encyclopedic knowledge of birthdays and life events for everyone in her extensive network and would never pass up an opportunity to spend time with those she loved.  She had amazing humor and wit, and her home served as a town square for family, friends, and neighbors alike to congregate and connect.

She somehow managed to make every person around her feel special, and she was very proud of the big, beautiful family she created. She could often be found creating delicious baked goods, enjoying the Red Sox games, on the winning side of a game of Scrabble, or down at the lanes of the Bowladrome.  She will be missed, but certainly never forgotten.

She was the beloved wife of the late John M. O'Leary. She was the loving mother of John "Jay" O'Leary, Jr. and wife, Debra of Reading, David O'Leary and wife, Alice of Hebron, NH, Peter O'Leary and wife, Barbara of Reading, Dana O'Leary of Winchester, Michael O'Leary and wife, Cindy of Holderness, NH, and Andrew O'Leary of Winchester. Barbara had 13 grandchildren and 22 great-grandchildren, as well as many nieces and nephews. Sister of the late John and Thomas Kinton, Donald, Samuel, David Kenton, Irene Mahoney, Polly Norris, and Jean Donovan. Stepsister of Thomas Treacy and the late Robert Treacy. Predeceased by her granddaughter, Betsy O'Leary Abelson and great granddaughter, Brooke.

The family extends a special thank you to the staff at Sawtelle Family Hospice House, Beatrice at ComForCare and Gini at Clark Care.

Her Funeral Mass will be celebrated in St. Mary Church, 155 Washington St., Winchester on Wednesday, Dec 21 at 11am. Visitation for relatives and friends at the McDonald Funeral Home, 19 Yale Ave., Wakefield on Tuesday, Dec 20 from 4-7pm. Interment, Massachusetts National Cemetery, Bourne on Thursday, Dec 22 at 12:30pm. In lieu of flowers, contributions may be made in Barbara's name to Betsy’s Park

To order memorial trees or send flowers to the family in memory of Barbara O'Leary, please visit our flower store.

Past Services


Tuesday, December 20, 2022

4:00 - 7:00 pm (Eastern time)

McDonald Funeral Home (MA)

19 Yale Ave, Wakefield, MA 01880

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Funeral Mass

Wednesday, December 21, 2022

Starts at 11:00 am (Eastern time)

St. Mary Church (Washington St)


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