David Raymond Headd's Obituary
David Raymond Headd, 85, of Fort Myers, Florida, passed away peacefully on November 19, 2025. Born on October 26, 1940, in Providence, Rhode Island, he was the son of the late Martin (Joe) and Beatrice (Cafferky) Headd.
David is survived by his loving wife of 22 years, Debbie (Ahlberg) Headd; his daughter, Patrice Headd of West Yarmouth, MA; and his stepchildren, Laura Hess and her husband, Jeff, of Dexter, MI, and Tom Pierce of Cape Coral, FL. He also leaves behind his sisters, Sheila Barrett of Yarmouth, MA, and Maureen Schneider of Duxbury, MA, and his sister-in-law, Sue Ahlberg of Bennett, WI; his grandchildren, Jessica Headd Federici and her husband, Chris, Charlie Stutzenberger, Olivia Stutzenberger, Clara Hess, and Henry Hess; and his great-grandchildren, Teddy and Peter Federici. He is fondly remembered as well by many nieces and nephews who cherished him dearly.
He was predeceased by his parents, Martin (Joe) and Beatrice; his brothers, Martin and James; and his daughter, Katherine.
David was raised in Walpole, MA, where his parents—Irish immigrants—operated the well-known Headd In Diner, a beloved and successful community restaurant. Growing up in a bustling family business shaped his appreciation for good food, hard work, and the value of community.
As a young boy, David loved playing sports. He was active in Little League and went on to play both football and hockey in high school and college. His high school football team notably won the State Championship.
David was a proud member of the Fraternal Order of Eagles #3957 in Cape Coral, the Cypress Lake United Methodist Church, and the Knights of Columbus. A devoted Husky, he earned his Bachelor of Science degree from Northeastern University. Though he eventually made his way to Florida to enjoy the warmer weather, he always held his Boston and New England roots close to his heart. David enjoyed a fulfilling 35-year career in real estate sales in Southwest Florida, where he was dedicated to helping his clients find their perfect homes and investment properties. Before his move to Florida, he enjoyed his work at Pratt & Whitney in East Hartford and at General Dynamics Electric Boat in Groton, CT.
Being on the water was David’s happy place. He learned to sail in his 30s off the coast of New London, CT, in the waters of Long Island Sound. His family has fond memories of sailing up and down the Thames River with David at the helm. His move to Florida offered a longer season for the water sports and scuba diving that he loved. In his spare time, he was an avid craftsman who enjoyed woodworking. He built beautiful tables for his family, each piece crafted with care and reflecting his skill and love. He was also known for his talent in fixing and repairing things around the house and his natural ability to figure out how things worked.
David also loved the game of cribbage, and he enjoyed many friendly, competitive matches with family and friends. He was a tremendous cook, a skill he lovingly inherited from his mother. David took great joy in preparing delicious meals and sharing them with his family.
David was known for his ability to spark lively, thoughtful conversations among friends and family. A natural conversationalist, he embraced the art of debate—not to win, but to connect, to listen, and to deepen his understanding of the world. With warmth and a sharp wit, he showed that even the strongest differences could be approached with curiosity, humor, and respect.
He will be remembered for his kind heart, generous spirit, and the joy he brought to all who knew him. His legacy endures in the love he shared and the memories held by those closest to him.
A celebration of life will be held on Saturday, January 10, 2026, at 11:00 a.m. at Cypress Lake United Methodist Church, 8570 Cypress Lake Drive, Fort Myers.
In lieu of flowers, memorial donations may be made to the Michael J. Fox Foundation or the American Parkinson’s Disease Association.
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