Helen grew up in Brighton, MA and graduated from St. Columbkille HS. She attended Burdett College, where she learned shorthand and secretarial skills. She went to work at a local insurance agency.
She met her first husband, Paul Flannery at a St. Col’s High School alumni dance in 1955 and they were married on May 23, 1959. They moved to Franklin, MA in 1960. Over the course of their long and happy marriage, Paul’s career took them to live in Chelmsford, MA, Gaithersburg, MD, and Waterford, CT. Paul and Helen Flannery had five children.
When Paul died in 1990, Helen took a position as a receptionist and eventually as legal secretary to the managing partner at Conway, Londregan & McNamara in New London, CT. There, she met Charles Sylvester, who she married in 2007. Helen was a life-long Red Sox fan, while Charlie was a die-hard Yankees fan, and they enjoyed many American League games together, in spite of—or perhaps because of—the rivalry. When Helen retired, they traveled together with friends and family, to New York, Italy, and Aruba. She was widowed a second time when Charlie died in 2014. In 2018, she traveled with children, nieces and nephews to Ireland, including a visit to the ancestral home of her grandfather, Patrick Barry, in Miltown Malbay, County Clare.
Helen was an active volunteer in every community in which she lived—in the school library, with Boy Scouts and Girl Scouts, in the neighborhood food co-op, and as the Clerk of Course for the local swim teams. She made and kept lifelong friendships with neighbors. She learned to play the piano as a child and was known to accompany many a family and neighborhood sing-along. While living in Maryland, Helen reveled in the history of Washington, DC, and was known to give expert tours of the White House, Capitol Building, Smithsonian Museums, and many monuments. She loved to play card games and, later in life, Mahjong. Helen never missed a day of solving the Jumble and Sudoku puzzles in the local paper and often completed the crossword. She played (and often beat) her opponents in daily games of Words with Friends. She was a devoted Catholic whose faith sustained her throughout her life.
Helen Flannery Sylvester is predeceased by her parents and by her husbands, Paul Flannery and Charles Sylvester. She survived by two sisters, Frances Benedict of Bellingham, MA and Joan Allsop of Port Orange, FL; five children, including Dennis Flannery (Trina), Teresa Flannery (Brian Blair), Dan Flannery (Jessica), John Flannery (Johna), and Patrick Flannery (Jacki), as well as Charlie’s three children, Tony Sylvestri, Karen Murray, and Dawn Jetmore; twelve grandchildren including Ryan, Katie, Lauren, Alex, Sean, Kevin, Julia, Kerry, Samantha and Jack Flannery, and Brigitta and Ashton Blair; three great grandchildren, Kaius and Skylar Lynch and Summer Flannery; many nieces and nephews and the extended Sylvester family, who adopted Helen as their own.
Family and friends are invited to call at Fulton-Theroux Funeral Home, 181 Ocean Ave., New London, CT on March 19th from 6:00 – 8:00 PM. A Mass of Christian Burial will be held at St. Joseph’s Church, Squire St., New London CT on Saturday, March 20th at 10:00 AM. Both events will observe local public health guidelines for masking and social distance.
SHARE OBITUARYSHARE
v.1.14.0