Carol P. DiMassimo, 87, passed away peacefully on August 18, 2026.
Born and raised in the Bronx, Carol was fiercely independent, resilient, and a perfectionist who took great pride in everything she did. She was artistic and creative, always interested in what those around her were doing, and never stopped keeping up with the lives and accomplishments of the people she loved.
Above all, Carol was a devoted mother, grandmother, and great-grandmother who was immensely proud of her family. She leaves behind her three children: Jay O’Connell; Lauren Rabin and her husband, David; and Karen Mackey and her husband, Patrick. She is also survived by her three grandchildren, Scott Rabin and his wife, Yuriko; Eric Rabin; and Fiona Mackey; as well as many nieces and nephews. Carol felt especially blessed to have met her two great-grandsons, Noah and Leo Rabin, and to see her family grow through four generations.
Carol graduated from Katherine Gibbs School and went on to build a career as an Executive Assistant at IBM. A longtime member of the Greenwich community, she was also proud to serve the Town of Greenwich as an assistant moderator at the polls in District 3.
Carol enjoyed life’s simple pleasures. She loved her soap operas, was always ready to dance, and treasured her rock collection, gathered over the years. She especially loved spending time at the beach—whether at Tod’s Point in Greenwich or Surfside Beach in South Carolina—where a good hot dog and a Diet Coke made the day complete.
For the last four years, Carol made her home at Nathaniel Witherell. Her family is deeply grateful to the staff and volunteers who cared for her, supported her, and filled her days with kindness and companionship. The family is also especially thankful to her wound care specialist, Dr. Wainwright, for her dedication and compassionate care.
Carol was predeceased by her parents, Charles Mayer and Sophie (Warona) Mayer; her brother, Robert Mayer; her first husband, Thomas O’Connell; and her second husband, Dominick DiMassimo.
Carol will be remembered for her independence and resilience, her curiosity about everyone and everything around her, and, most of all, the tremendous pride and joy she found in her family. She will be deeply missed.
Family and friends are invited to pay their respects on Friday, August 21, from 4:00 to 8:00 p.m. at Castiglione Funeral Home. Burial will take place on Monday at Putnam Cemetery.
Instead of flowers, the family asks that you consider donating in Carol’s memory to the Friends of Nathaniel Witherell, in gratitude for the care and companionship she received during the final years of her life.