REGAN, Dennis K, of West Roxbury, MA, passed away peacefully on December 20, 2025, at his home surrounded by his loving family. Beloved husband of Marilynn (Cunniff) Regan. Loving father to Dennis K. Regan Jr. and his wife Heather of West Roxbury, Courtney A. Bernazzani and her husband Michael of West Roxbury, Caroline R. Murphy and her husband John of West Roxbury, Terrence (TJ) Regan and his wife Jessica of Medford, and Michael A. Regan and his wife Erin of West Roxbury. Proud “Papa” to Shane, Audrey, and Allison Bernazzani, Frankie, Cecelia, Avery, and Nolan Dennis Regan. Cherished brother of James D. Regan III and his wife Colleen of Westford, MA, Bernard A. Regan and his wife Grace of West Roxbury, Lisa Regan of West Roxbury, Clare O’Donnell and her husband Edward of West Roxbury, and the late Mark T. Regan. Dennis is also survived by his brother-in-law and best friend Bob Lepardo, of West Roxbury, as well as many cousins, nieces, and nephews.
Born in Boston on November 3, 1950, son of James and Mary Regan, he was one of six children and shared a unique and genuine bond with each of them. Dennis proudly called West Roxbury home, building a remarkable circle of friends that spanned generations, communities, and walks of life.
Dennis attended Don Bosco Technical High School, where he was a standout football, hockey, and baseball player. His love for sports remained a constant throughout his life, including the proud accomplishments of running the Boston Marathon in 1984 and 1988, and later led him to years of officiating football at the high school and college level, alongside his brother, Jimmy - something he deeply enjoyed.
Shortly after high school, Dennis met the love of his life, Marilynn (Mal) and they married March 15, 1972. Together, they raised five children - Dennis, Courtney, Caroline, TJ, and Michael - whom he devoted himself to at every opportunity.
As the family grew, Dennis found his greatest joy gathered around the table with Mal, their children, grandchildren, extended family, and friends sharing stories and laughter at was affectionally known as the “Regan Family Fun Center.” The addition of an inground pool became a gathering spot for many from Memorial Day to Labor Day. Around it, tables were filled with food and drinks, music played, and Dennis, often the source of laughter, kept everyone smiling, creating cherished memories.
Dennis worked for Boston Gas. He was a proud member of United Steelworkers Union, Local 12003 for 46 years where he formed many lifelong friendships.
Outside of his career, Dennis was a familiar face behind the bar at Triple D’s, Kelleher’s, and The Happy Hour, where he served cold beer, witty jokes, and warm conversation.
Most recently, Dennis enjoyed spending time at the BPOE Elks Lodge #10 laughing with old and new friends, especially his best friend, Bob, and spending many happy times watching his grandchildren play the sports they loved.
Visiting Hours at the William J. Gormley Funeral Home, 2055 Centre St. West Roxbury on Sunday, December 28 from 3pm-7pm. Funeral from the funeral home on Monday, December 29 at 9am followed by a Mass of Christian Burial in St. Theresa of Avila Church at 10am. Interment private.