"It makes you question the value of what Sears is sitting on," he said. "It may have to continue dismembering itself to stay alive today and shrink from inside out. "
Sears has spun off other businesses over the past two years, including its Hometown and Sears Outlet stores and its Orchard Supply Hardware Stores, to raise cash.
Sears Chairman and CEO Edward Lampert disclosed recently that his stake in the company has been reduced to less than 50 percent as investors pulled money out of his hedge fund.
The news underscores the intense pressure facing the billionaire hedge fund manager, who took over as CEO in February to turn around the business.
Sears and the company's Kmart chain have struggled as rivals have lured away customers over the years.
Last year, Sears announced plans to restore profitability by cutting costs, reducing inventory, selling off some assets and spinning off others. Those moves helped it reduce net debt by $400 million and generated $1.8 billion in cash from the asset sales in the latest fiscal year.
Sears also has been building a loyalty program called Shop Your Way, which accounts for 65 percent of its sales and has tens of millions of active customers.
Still, Sears continues to face losses. In November it reported a wider third quarter loss as revenue declined 7 percent to $8.27 as the company marked down goods heavily to move merchandise.
Lands' End, which sells clothing and home goods on the Internet and through catalogs, began in 1963 as a sailboat hardware and equipment catalog, but morphed into a clothing company by 1977. Sears bought the company in 2002.
Sears shares slipped 4 cents to $49.94 in morning trading. They are up almost 21 percent so far this year.