The "You Might Well Arsk" sale of the late Beatles singer's material is scheduled to take place June 4 in New York, Sotheby's said.
The items are being put up for sale by Tom Maschler, who had worked with Lennon on "In His Own Write" and "A Spaniard in the Works." Lennon wrote the books and created the drawings for them in the 1960s.
Among the items in the auction is a manuscript from 1965 called "The Singularge Experience of Miss Anne Duffield," which is expected to sell for $40,000 to $60,000. Another is an illustration of a guitar player with four eyes, which Lennon created in 1964 or 1965. It has a presale estimate of $15,000 to $25,000.
The auction comes in a high-profile year for Beatles nostalgia. Fifty years ago, in February 1964, the Beatles made their first live U.S. concert appearance. A piece of the stage backdrop will be up for auction April 26 in New York City.
Lennon was fatally shot in 1980 by Mark David Chapman, who has been denied parole seven times.