Winfield was happiest performing on stage, particularly in the works of Shakespeare. He also appeared in numerous plays by modern writers.

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Winfield's avocations included home renovation, an interest that he shared with Gillan; playing the cello; and raising champion black pug dogs, whom he named after characters from his beloved Shakespeare. He also became an avid collector of objects depicting the breed, accumulating hundreds of bronze and ceramic figures, including a 600-year-old sculpture from China.

While at a dog show in Denver in the late 1990s, Winfield fell into a diabetic coma and required three weeks of hospitalization. This caused him to "take [the disease] seriously" and to speak out publicly to make African-Americans more aware of the dangers of diabetes and obesity. He was also a vocal proponent of civil rights. Within the entertainment industry he worked tirelessly to promote cultural diversity.

Winfield did not, however, play an active role in the gay rights movement. His friend actor-producer Jack Larson described him as "openly gay in his life if not in the media." Indeed, in a 1990 article in People Weekly Tim Allis wrote that Winfield "mentions no current relationship," although he and Gillan had by then been partners for well over a decade.

One cannot say with certainty why Winfield chose to maintain public silence regarding his sexual orientation. It may be noted, however, that many actors of his generation, such as Rock Hudson and Richard Chamberlain, long concealed their homosexuality for fear of losing employment.

Larson stated that Winfield had been distraught in his final years due to Gillan's death. Winfield died of a heart attack on March 7, 2004 in Los Angeles.

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