Robert Joseph “Bob” Intravaia, 88, of Winchester, Massachusetts, passed away peacefully on January 20, 2026, surrounded by the family he loved so deeply.
Bob was born on December 28, 1937, in Boston’s West End to Domenico Intravaia and Concetta (DiFranco) Intravaia, both of Augusta, Sicily. As the youngest of seven children, he grew up in a loud, loving home where family came first, a value he carried with him throughout his life.
Bob graduated from Somerville High School, where he was a standout halfback on the football team, and later attended Northeastern University. He believed that grit and perseverance mattered more than schooling alone, and he paired that with an entrepreneurial spirit, always thinking of new ideas. He began his career at Grolier Inc. before taking a leap of faith to found his own company, CTI, Inc. Through persistence, integrity, and tireless effort, he built the company into a successful business he was immensely proud of. A true businessman at heart, Bob loved following market trends, discussing investments, and staying engaged with the financial world. His curiosity and sharp instincts never waned.
Bob loved to travel, especially to his home in Marco Island, Florida, trips to Italy to connect with his roots, cruises to Bermuda, and simple day trips to Gloucester. He also cherished a good Sunday drive through his old neighborhood or with no particular destination, simply enjoying the company of family. More than any place, he treasured being with those he loved, and a houseful of family and friends was where he felt happiest. He loved Wednesday night card games, Sunday dinners, watching the Patriots with his grandchildren, Labor Day clambakes, surprise visits to family marked by his special knock, and reminiscing about the old days. He had a special gift for staying connected and making everyone feel remembered. Tennis brought Bob great joy and lasting friendships over the years. He was a constant presence at the Winchester Packer Tennis Courts, there day after day, always looking for a game or enjoying a match with his tennis friends. He also treasured many summers as one of the early members of the Winchester Swim and Tennis Club.
Bob is survived by his devoted wife of 65 years, Phyllis (Picardi) Intravaia; his daughters Patricia Cronin and her husband Alfred of Woburn, Diane Cipro and her husband Christopher of Winchester, and Leanne Christmas and her husband Jonathan of Winchester. He was a proud and devoted grandfather to seven grandchildren, Kaitlin, Robert, Meghan, Alyson, Jonathan, Samuel, and Alexander who were the absolute joy of his life. He never missed a chance to cheer them on and was endlessly proud of each one. He leaves behind his treasured nieces, nephews, grand-nieces, and grand-nephews, with whom he maintained a close and loving connection throughout his life. Bob will be remembered for his generosity, love of tradition, authenticity, and deep devotion to his family. His presence was constant, his support unwavering, and his love unmistakable. He leaves behind a legacy defined by family, loyalty, and a life well lived.
A Funeral Mass will be held on Saturday, January 24, 2026, at 10:00am at St. Mary's Church, 155 Washington St., Winchester. Relatives and friends are kindly invited to attend and are asked to meet directly at the church. Burial will follow in Wildwood Cemetery, Winchester. In lieu of flowers, the family kindly asks that donations be made in Bob’s memory to the Make A Wish Foundation https://wish.org/donate-make-wish-today or the Tunnel to Towers Foundation https://t2t.org/donate/ reflecting his lifelong generosity and love of helping others.