Maureen O'Brien

Maureen O’Brien (Greenwood), a devoted wife, mother, sister, and friend, left the world peacefully at home on August 22, 2026, at 78 years young.

Maureen leaves behind her husband of 56 years, Philip O’Brien; her daughters, Stephanie O’Brien and her partner Dave Connolly of East Boston, and Jill O’Brien and her fiancé Kevan Bradley of Malden; her sisters, Gayle and Debbie Greenwood of Malden; her brother, Bill Greenwood and his wife Kathy of Dracut; and many beloved nieces, nephews, cousins, friends, and Doodhuts.

Maureen graduated from Malden High School in 1966, continuing her education at Cardinal Cushing College, where she trained to be a medical secretary. A hard worker, she helped build a successful air freight company, and worked nights while being the CEO of her household.

Maureen was a collector of friends. Whether you were a neighbor, a classmate, a colleague, or a stranger in the grocery aisle, she had the kind of presence that put you at ease and made you want to share your stories.

She was a natural caregiver who quietly looked after those around her. Quick to find humor in any situation, her laugh was contagious. Making her laugh was one of life's greatest joys, and no one could make her laugh quite like her husband, Phil.

Of all the roles she held in life, the one she loved most was being "Mimi" to her five grandchildren: Maisey O’Brien, James and Maren Connolly, and Finnegan and Sylas Bradley. They will dearly miss her grilled cheese sandwiches, sleepovers, baking cookies together, and most of all, her warm hugs. She left an extraordinary impact on all of us fortunate enough to know her, and she will be deeply missed.

Visitation for relatives and friends will be held at the McDonald-Finnegan-Anderson Funeral Home, 322 Main St. Stoneham, MA 02180 on Monday, August 31, 2026, from 4-7 pm. Her Funeral Mass will be celebrated on Tuesday, September 1, 2026 at 10:00 am at Saint Patrick’s Parish, 71 Central Street Stoneham, MA 02180.

In lieu of flowers, memorial contributions can be made to the Jacqueline Greenwood Memorial Scholarship c/o Cotting School; 453 Concord Ave. Lexington, MA 02421 or Mass General Brigham Cancer Institute https://giving.massgeneral.org Mass General Giving, 399 Revolution Drive Suite 1330, Somerville, MA 02145