Helen Flannery Sylvester

November 3, 1937March 11, 2021

Helen Catherine Esterbrook Flannery Sylvester, was born on November 3, 1937 in Somerville, MA, to parents Robert and Helen Esterbrook.

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.


  • Calling Hours

    Friday, March 19, 2021

  • Mass of Christian Burial

    Saturday, March 20, 2021


Helen Flannery Sylvester

have a memory or condolence to add?

Dennis Flannery

March 20, 2021

Mom loved to dance; especially with Dad or anyone of her children and grandchildren. After Dad passed, I took any opportunity I could to dance with her. In 2018, at her 80th birthday party, in the kitchen at Dan’s shore house, I caught mom in a pensive moment. I asked her what she was thinking about, and she simply said, ‘Dad’. So I asked her to dance. He face lit up, and we danced for a few minutes. But she didn’t have much stamina and, though she was on oxygen, was quickly out of breath. She kissed me and hugged me with bittersweet tears in her eyes, and thanked me for the dance.

Now she can dance with Dad and Charlie. I miss dancing with you Mom.

Commissioner Vannessa Dorantes

March 15, 2021

John -- Although I did not have the pleasure of ever meeting your mom, the beautiful words in this obituary reflect what a wonderful person she was. This photo is absolutely lovely. You have acclimated very well to the DCF "family" and it is now abundantly clear where you got your compassion and kindness for others from :)

May you and your family be comforted by the many fond memories.
The State of CT Dept of Children and Families Exec Team


March 13, 2021

My sincerest condolences on the passing of Helen. She was such a regal and elegant person and a part of my youth that I'll remember fondly. May she rest in peace.