Schilling has said he invested as much as $50 million in 38 Studios and has lost all his baseball earnings. He told WEEI-AM in Boston last year that possibly having to sell the sock was part of "having to pay for your mistakes."
"I'm obligated to try and make amends and, unfortunately, this is one of the byproducts of that," he told the station.
Brad Horn, a spokesman for the hall of fame in Cooperstown, N.Y., said the loaned sock was returned in December under the terms of the hall's agreement with Schilling. The hall had had it since 2004.
The Feb. 23 live bidding will be held at the Fletcher-Sinclair mansion in New York City, now home to the Ukrainian Institute of America. The auction will feature other "five- and six-figure items," including a jersey and cap worn by New York Yankees great Lou Gehrig, Ivy said.
Heritage last May auctioned off the so-called "Bill Buckner ball," which rolled through the legs of the Red Sox first baseman in the 1986 World Series. Ivy said that item, like Schilling's sock, was listed at the time as being expected to bring in "$100,000-plus," but it was sold to an anonymous bidder for $418,000.