The Ayrshire serial entrepreneur is understood to own around 26% of Prestbury, which intends to float the portfolio on the AIM market this year in a move expected to value it at around £1.5 billion in total.
The stake in the portfolio, developed with property veteran Nick Leslau, will become Sir Tom's biggest investment in a quoted company.
News of the plan comes days after Sir Tom sold his 11% stake in House of Fraser to retail tycoon Mike Ashley shortly before the department store business was sold to China's Sanpower for £480m.
The flotation of the Prestbury portfolio could pave the way for Sir Tom to recoup some of the hefty losses he has incurred on his investments in property in recent years.
After selling Sports Division for £290m in 1998, Sir Tom made investments in firms including McCarthy & Stone and Crest Nicolson that plunged in value when the property market slumped in 2008.
He subsequently said he made a huge mistake investing in housebuilders at the tail end of the last boom.
But the Prestbury operation run by Mr Leslau has developed a profitable business based on investing in properties that are let to others on long leases.
Tenants include the Merlin Entertainments group, which operates attractions like the flagship Madame Tussauds waxworks in London and Alton Towers theme park in Staffordshire.
The company believes there is scope to achieve significant growth.
The listing would help the company to buy up more properties from banks and the like in exchange for shares. The company could also tap stock market investors for funds to supplement the debt it could raise from lenders.
Sir Tom has been involved in a series of property deals with Mr Leslau since 2001, when the two men launched a £166m joint venture to buy three major commercial properties, including the Babcock industrial estate next to Glasgow airport.
Bank of Scotland provided significant backing for Sir Tom's moves in the property market while it was part of the HBOS operation.
Lloyds Bank, which completed a rescue takeover of HBOS in 2008, is a shareholder in Prestbury .
Mr Leslau gave away £400,000 to residents in Glasgow after appearing on the Secret Millionaire television show in 2008.
A spokesman for Sir Tom declined to comment on Prestbury.