Robert Gordon Roles Jr.

August 2, 1944 – July 5, 2026

Robert Gordon Roles, Jr. (Bob), 81, passed away peacefully on July 5, 2026, at Brigham and Women’s Hospital, surrounded by his children. The cause of death was complications due to a stroke he had suffered in May.

Bob was born on August 2, 1944, in New Canaan, Connecticut, to Robert and Mary Elizabeth (Kelley) Roles. At the age of fourteen, he attended Cardinal Farley Military Academy, every year participating in the New York St. Patrick’s Day Parade, highlighted by a traditional Irish dinner at a family friend’s house.

After Cardinal Farley, Bob went on to Georgetown University, graduating with a Business degree the day before his eldest daughter was born. After graduating, Bob joined the family firm, Roles Inc. (real estate, land surveying, and building inspection), but Bob was a Carpenter at heart and soon set out on a different path.

From a young age, working at a Lumber company in New Canaan, Bob found satisfaction in physical labor and passion in designing and building beautiful homes on Candlewood Lake and surrounding areas in New Fairfield.

The first home Bob built was for his family in a neighborhood that he knew well—Knollcrest. He had spent childhood summers on Candlewood Lake boating (often saying he had the fastest boat on the lake), skating in the winter, fishing, growing up and hanging with the “Knollcrest crew.”

So naturally, buying a small piece of land at the end of Crest View Rd. on Knollcrest, and building a home for his quickly growing family, was what Bob set out to do—providing a wonderful neighborhood and home to raise his children.

An athlete throughout his life, Bob loved sports, fast cars, and fast boats. He was an exceptionally hardworking man who believed in doing things the right way; he also wasn’t afraid to tell you the “right way.”

His quick wit and dry humor were equally memorable. He had a quiet, generous spirit, often helping neighbors, friends, and family. He never forgot a birthday and was often the first voice his children heard with a heartfelt birthday message. There was never a dog that Bob met that he didn’t immediately love.

Later in life, Bob made Cape Cod his home to be closer to his eldest daughter, Laurie. There he embraced the simple routines he loved most. Like clockwork, his daily routines were important to him. He enjoyed fishing, cooking a good meal, watching football, scratch tickets, tending to his plants, spending time, and lovingly caring for his elderly dog,Tiger.

Sunday football with Laurie became a regular cherished time for both, and together they shared home-cooked meals and rooted for the Giants and the Bills. After football season, they played many, many games of Gin Rummy, most of which he won.

Bob was predeceased by his parents, Robert and Elizabeth Roles; his sister, Betty; and his beloved canine companions, Curry, Brandy, and Tiger.

He is survived by his four children; Laurie Roles, Karen Pape (Jack), Robert Roles (Noelle),Heather Roles, his eleven grandchildren, five great-grandchildren, and his beloved niece and nephew, Anne Thomson and Chip Taddei.

In his final days, Bob was graceful and brave, surrounded by all four of his children, along with stories, music, poetry, laughter, tears, and love. Those who knew him will remember a man of quiet strength, unwavering integrity, and kindness.

A memorial visitation will be held at the Doane, Beal, & Ames Funeral Home, 729 Rt. 134, South Dennis, MA on Saturday, September 19, 2026 from 1-3 PM.