Born in 1936 in Prague, Czechoslovakia, Winn is one of two daughters of a psychiatrist; her sister is the writer Janet Malcolm. Winn is a U.S. citizen who attended the Bronx High School of Science, Radcliffe College and Columbia University.

In May 1958, while Winn was a contestant on Dotto, a notebook which belonged to her was found by another contestant, Ed Hilgemeier, who discovered that the notebook included questions and answers to be used during Winn's appearances. Jack Narz, the host of Dotto at the time, recalled, when interviewed for a PBS documentary, that he believed Winn to be "a little too pat" when giving her answers. A CBS executive vice president, Thomas Fisher, tested kinescopes of the show against Winn's notebook and concluded that the show appeared to have been fixed. The executives also learned the show's producers had paid Winn, Hilgemeier, and Winn's opponent Yaffe Kimball-Slatin to keep quiet about the notebook. They also learned that Hilgemeier might have demanded more money to keep quiet and filed a deceptive practices complaint with the Federal Communications Commission.

The Plug-In Drug

Winn is the author of the influential The Plug-In Drug (1977), an often scathing critique of television's addictive influence on the young, Winn wrote, "The television experience allows the participant to blot out the real world and enter into a pleasurable and passive mental state." In 2002, she added new material to update the study as The Plug-In Drug: Television, Computers, and Family Life, published on the 25th anniversary of the original book.

Pale Male

An advocate for protecting wildlife, Winn gave the name Pale Male to the Red-tailed Hawk that nested on a Fifth Avenue building, receiving much press coverage. She was also prominent in preserving Pale Male's nest when it was threatened with removal. She wrote about these events in her book, Red-Tails in Love: Pale Male's Story - A True Wildlife Drama in Central Park (1998). The book is an expansion of her Smithsonian magazine articles and her column in The Wall Street Journal. Frederic Lilien's documentary film, Pale Male (2002), is an adaptation of Winn's book and includes interview scenes with Winn.