Winters married Dean Stevens Vernon (1926–2001), a sound Engineer on Sky King, and gave up acting following a 1960 appearance on Hugh O'Brian's ABC western series, The Life and Legend of Wyatt Earp.

Winters went on to a Pete Smith movie short, in a scene of her coming down a slide to the grass, where a black Scottie dog licked her face. She also appeared in an Our Gang feature. She performed onstage, and took tap dance classes, and in the late 1940s and early 1950s was first cast in Western films such as Driftwood (1947) and El Paso (1949), and in such television series as The Lone Ranger and The Range Rider. Her roughly twenty films, mostly Westerns, include The Lawless (1950) and Gambling House (1950).

She portrayed daughter Babs Riley in the first season of the NBC sitcom The Life of Riley (1949 to 1950), starring Jackie Gleason and Rosemary DeCamp. The show was subsequently recast with william Bendix in the lead.

Winters' signature role was in the television drama Sky King, starring Kirby Grant as rancher and pilot Schuyler "Sky" King in Arizona of the 1950s. Winters played the blonde, baby-faced, perky but earnest and helpful teen-aged niece, Penny King, who lived with her uncle at the Flying Crown Ranch and often became involved in his varied adventures. She played the role in seventy-two episodes from 1952 to 1959. Ron Hagerthy is the same age as Winters, and appeared in nineteen episodes during 1952 as Sky King's nephew, Clipper King, but it was not clarified if Clipper was the brother or the cousin of Penny. Sky King ran on NBC and ABC, and was filmed in 1951 to1952 and from 1955 through at least 1959, as sponsors changed. It ran thereafter in syndication, but the actors received no residuals.

In the interim, Winters had guest roles in series, including the anthology Death Valley Days, The Jack Benny Program, Richard Diamond, Private Detective; Racket Squad; The Gene Autry Show, in which she made her singing debut in the 1951 episode "Warning! Danger!", The Adventures of Wild Bill Hickok, Brave Eagle, Four Star Playhouse, General Electric Theater, Frontier Doctor, Judge Roy Bean (in the episode "Four Ladies from Laredo"), The Roy Rogers Show, and Sheriff of Cochise.

During this time, Winters appeared in movies, including Hold That Line (1952), starring the Bowery Boys, and She Couldn't Say No.

Winters appeared, too, in a recurring role as Ruth Farley in the 1953–1955 ABC sitcom with a variety show theme, Where's Raymond?, renamed The Ray Bolger Show. Verna Felton played her mother. The series starred Ray Bolger as Raymond Wallace, a song-and-dance man who was repeatedly barely on time for his performances.

In 1964, Winters wrote Penny's Guide to Teen-Age Charm and Popularity (Prentice Hall), an etiquette book aimed at young girls, which inspired the alternative rock band Nada Surf's 1996 song and video "Popular." As well, Jimmy Buffett's song "Pencil Thin Mustache" contains a reminiscence of being about "bucktoothed and skinny ... writin' fan letters to Sky's niece Penny."

Gloria Winters grew up in the San Fernando Valley of Los Angeles, and later moved to Hollywood with her family. A child Actress, she made her debut, she said in a mid-2000s radio interview, "when I was about five," with a small role in a Shirley Temple movie. "I came running out to Shirley Temple, and she was supposed to help me, like I had just gone to the little girls' room." (One source says she had appeared as a baby in the 1932 Carole Lombard film Virtue.)

When her husband retired, the two moved to Vista, California. He died in 2001, and Winters succumbed nine years later of complications from pneumonia at her home. She was survived by her sister-in-law Phyllis DeCinces, and was interred alongside her husband at the Fort Rosecrans National Cemetery in San Diego.

In 2002, she was awarded the Motion Picture & Television Fund's Golden Boot Award for her work in Western films and television programs.