JumpStart Toddlers is a game that was released in 2000. It replaced the original 1996 version, and would later be re-released as part of JumpStart Advanced Toddlers and JumpStart Advanced Preschool. It is also known as Jump Ahead Toddlers 2000 and Jump Ahead 2000 Toddlers II in Europe.
- Grandma's Flower Garden - See colorful flowers and play with the butterfly in Grandma's garden. In level one, the player can press any keys or move the cursor over the butterfly to make the butterfly and flowers change colors. In level two, the player has to click on the flower that is the same color as the butterfly's wings.
- Chippy's Treehouse - Watch Chippy make different shapes. In level one, the player can press any key or click on one of the boxes to watch Chippy make a shape. In level two, the player has to select the shapes that Chippy needs to make toys.
- ABC Toadstools - Learn about letters with Mr. Mouse and the ABC Mice. In level one, the player can press a letter key, and that letter will appear on Mr. Mouse's house, and Mr. Mouse will bring out an item that begins with that letter. If the player presses a non-letter key, a random letter will appear on the house. In level two, there are three toadstools, and the player has to match items with their beginning letters.
- Lily Pond - Count the animals swimming in the pond. In level one, the player can press any key, and a snail with a number on it will light up, that number of animals will swim out into the pond, and DeeDee will count them. If the player presses a number key, the snail with that corresponding number will light up. The player can also move the cursor over a snail to make it light up. In level two, DeeDee will ask the player to count the number of animals in the pond. The player selects their answer by moving the cursor over a snail or pressing a number key. Three types of animals can appear in the pond: fish, frogs, and turtles.
- Peek-a-Boo Woods - Find hiding animals in the woods. In level one, a layer of flowers, leaves, or butterflies will cover the screen. The player can press any keys or move the cursor to clear away the objects and find an animal underneath. Once a certain amount of the screen has been cleared, the rest will automatically clear away on its own. In level two, the player has to match baby animals to their parents. The player has to move their cursor over a hiding spot when they see the baby animal that matches the parent animal.
- Picture Playtime - Here, the player can freely create their own pictures by painting, coloring, and placing stickers. The player can save up to ten pictures at a time.
- Musical Waterfall - Here, the player can make music. The player can press any key to make one of the musicians player their instrument, or move their cursor over a musician to make that musician play their instrument.
- At Grandma's House
- Chippy's Shapes Song
- Grandma's Flower Garden
- Counting in the Pond
- Picture Playtime
- The ABC Toadstools
- Peek-a-Boo Woods
- The Musical Waterfall
- Finale: (Leaving Grandma's House)
- Counting (1-10)
- Memory Skills
- Mouse Control
- Cause and Effect
- Listening Skills
- Similarities and Differences
- Beginning Vocabulary
JumpStart Toddlers received a Deluxe release circa 2000, which included the bonus disc "My Learning Scrapbook".
JumpStart Toddlers was re-released as JumpStart Advanced Toddlers: School Time in JumpStart Advanced Toddlers. It was later re-released as JumpStart Advanced Preschool: Toddlers School Time circa 2007.
- This game is one of the few examples of an updated version of a game from the classic series which features a completely new cast of characters and setting with no resemblance to those in the original title. It shares this trait with JumpStart Adventures 4th Grade: Sapphire Falls.