Four theatrical Toy Story films were released between 1995 and 2019: Toy Story, Toy Story 2, Toy Story 3, and Toy Story 4.
The series began with Toy Story on November 22, 1995. Toy Story 2 followed on November 24, 1999, expanding Woody and Buzz’s world while revealing Woody’s history as a television character. Toy Story 3 arrived on June 18, 2010, as Andy prepared to leave for college. Toy Story 4 was released on June 21, 2019, and followed Woody’s new life with Bonnie and the introduction of Forky.
A common mix-up is counting Lightyear, released in 2022. It is a spin-off about the fictional space hero who inspired Buzz Lightyear’s toy, not the fifth entry in the main Toy Story storyline. Likewise, Toy Story Toons and other shorts do not count as theatrical feature films.
The wording’s date range is important: it ends in 2019, so later projects cannot change the answer. The count is therefore four main-series theatrical features released during that period.