Boats 02

Robert Lee Benner

December 13, 1955 ~ August 15, 2019 (age 63)


Robert Lee Benner, 63, passed away peacefully and surrounded by loved ones on August 15, 2019. He was the son of Marilyn Benner and Ray Hyler and grew up in Cushing, Thomaston, Rockland and Port Clyde, Maine. The coast of Maine was one of his favorite places, and he enjoyed visiting often.

After graduating from the University of Southern Maine in 1980, Bob spent the last forty years working in the IT profession in the Boston area and was a resident of the town of Winthrop, Massachusetts. The family of friends he built through his professional and Winthrop communities is something he loved dearly. 

Bob enjoyed fishing and watching sports of any kind. As an avid fan of the Red Sox, Patriots and Celtics, he took great pride in sharing his passion for sports with those around him. You could also always count on Bob for a good laugh. He never allowed himself or those in his company to take life too seriously.  

His greatest pleasure was spending time with his daughter Tracey, the light of his life, and her husband, Sean Kimsey. He will be greatly missed by all who loved him, including his siblings Michael Benner and his wife Marianne, Ramona Benner, Joyce Maxcy and her husband Russell, Ann Frisbie and her companion Greg Morris, Heidi DiMauro and her husband David, Randy Hilt and his companion Linda Stewart and Gail Moreau. In addition to his siblings, Bob is survived by many nieces and nephews who he adored.

There will be a private family gathering in Maine to celebrate his life. In honor of Bob, donations can be made to The Home Base Program (

To send flowers to the family or plant a tree in memory of Robert Lee Benner, please visit our floral store.


You can still show your support by sending flowers directly to the family, or by planting a memorial tree in the memory of Robert Lee Benner
© 2020 Ernest P. Caggiano & Son Funeral Home. All Rights Reserved. Funeral Home website by CFS & TA