Stephen Charles Winfrey passed away peacefully at his home on Saturday, December 27, 2025, surrounded by the comfort of a life well lived and deeply loved.
Steve was born on March 28, 1950, in Newport News, Virginia, to Harry “Sam” Winfrey, Jr. and Mary Kelley Winfrey. He graduated from Ferguson High School in 1968 and went on to spend much of his working life in construction, traveling and working throughout Virginia, Arizona, and Ohio. In 2012, Steve retired from Greenfield Homes in Newport News, but retirement did not slow him down. He went on to enjoy his later years working at Woodlands Golf Course in Hampton, Virginia, a place that reflected his love of the great game.
From a young age, Steve loved sports, football, swimming, and baseball, and that passion stayed with him throughout his life. He took great joy in watching his children and grandchildren compete, and when he couldn’t be there in person, he always made sure to ask how they did. A devoted fan of the Dallas Cowboys, Steve proudly embraced his identity as a cowboy at heart, a spirit reflected in his grit and strength.
Steve found joy in cooking for others, spending time on the golf course, and sharing laughter with family and longtime friends, especially his dear friend Earl Meredith. He loved working with his hands and was always willing to lend his time, skills, and heart to help someone in need. Though he carried himself with a tough exterior, those who knew him best knew his true nature. He was generous, dependable, and deeply caring. He never hesitated to show up for others, whether family, friend, or stranger in need of a helping hand.
Steve was preceded in death by his parents, Harry “Sam” Winfrey, Jr. and Mary Kelley Winfrey; his brother, Harry “Sammy” Winfrey III; his sister, Sharon McEnerney; and his nephew, Connor Tolbert.
He is lovingly remembered by his wife of thirty-three years, Debbie Winfrey; his sister, Sandra Wolpert of Newport News; his daughter, Amy Higgins, and her husband, Brennan, of Portland, Oregon; his sons, Cam Winfrey and wife Johnna of Siloam Springs, Arkansas; Zachary Winfrey and wife Lauren of Falls Church, Virginia; and Dylan Winfrey of Hampton; as well as his eight beloved grandchildren: Jaxson Nolen and wife Emily, Ryder Winfrey, Ty Clayton, Ella Higgins, Kellen Winfrey, Hudson Winfrey, Keyes Winfrey, and Adelaide Winfrey. He is also survived by many extended family members and friends who will forever carry his memory in their hearts.
There will be a Celebration of Life Service at 1:00 p.m. on Friday, January 2, 2025 at Peninsula Funeral Home, 11144 Warwick Blvd, Newport News, VA 23601, followed by a reception at Smoke BBQ Restaurant and Bar, 10900 Warwick Boulevard, Newport News, VA 23601.
2 Comments
Such a wonderful photo and beautiful tribute to Steve. I’ve been so blessed to have Steve and Debbie as my neighbors for over 30 years. Yes, Steve was tough and stoic, yet I’ve seen his caring soft heart too. He showed it by helping another neighbor who was a virtual stranger living across from him re-install siding that blew off their home. Such a kind act by him. He saw me struggling to dig out a flower bed years ago on the side of my home and showed up without saying a word with a tiller. I’ll never forget this and all the wonderful tomatoes and squash gifted to us by him and Deb too. Will miss seeing him happily tending to the garden he adored.
My deepest condolences to Debbie who was the perfect fit as a wife to Steve and mother to Dylan. Though I didn’t know Steve’s entire family, please accept my prayer of healing for all of you and may your memories of him ease the pain in your hearts.
Blessings and deepest sympathy,
Susan Eareckson-Butler
Steve will be so sorely missed. I couldn’t have asked for a better neighbor all these years. May his memory be a shining light in the darkness for all those who knew him. All my love to his family and friends. ❤️