Sylvia Winfield is a former neighbor of the Simpson family. She and her husband Mr. Winfield lived next door until they moved to Florida and Ruth and Laura Powers moved into their house. It was explained that they despised the Simpson family so much they moved away. They laughed as Homer contemplated suicide.
- In "Dead Putting Society", Sylvia is one of the people at the library saying "hi" to Lisa, so she doesn't despise all of the Simpson family.
- In The Simpsons: Hit & Run, two pedestrian templates are modeled after her, one in a pink dress and one in a blue dress.
 Behind the Laughter
In "Bart's Dog Gets an "F"", she is voiced by guest star Tracey Ullman. In her other appearances she is voiced by series regular Maggie Roswell.
The couple also appear in the opening credits of The Simpsons during the segment where Marge and Maggie pass many characters while driving home.