A court this week granted an Australian Tax Office request to have $24.9 million in assets frozen belonging to Mr Leaver as part of the watchdog's Project Wickenby.

Mr Leaver's expansive beachfront home in Point Piper which includes a lap pool overlooking Blackburn Cove, a double-storey terrace on Paddington's fashionable Sutherland Street that is mortgaged to his daughter Sophie Leaver and the family's retreat in Glenquarry in the Southern Highlands of New South Wales have all been frozen by the Federal Court.

Mr Leaver, who owns several horses with broadcaster Alan Jones, has also had the assets of his thoroughbred trading company frozen.

Assets held by Mr Leaver's Gibraltar business Southfields Investments, his London company Normandy Finance and Investments and British Virgin Islands incorporated vehicle Hesley Consultants are also subject to freezing orders. Several bank accounts held by Mr Leaver and his family have also been frozen.

The tax office has also won a separate freezing order over the assets of Russell Associates – a company described in court documents as being incorporated in the British Virgin Islands and controlled by Vanda Gould.

Separately, the Australian Taxation Office has launched action against Mr Gould to recover a $14.5 million tax bill which includes the alleged non-payment of personal income taxes and the Medicare Levy over a ten-year period from 2001.

Lawyers for Mr Leaver did not respond to inquiries.

Mr Gould's lawyers declined to comment but it is understood he will object to the amended tax assessment.

It's not the first time Mr Gould and Mr Leaver have found themselves in the sights of the ATO. In October 2013 they were both arrested by Federal Police for money laundering in evening raids at their Sydney homes following an investigation by the ATO's Project Wickenby team.

The criminal charges against the men were dropped in May 2014 and the court ordered the tax office pay their costs over the botched investigation.

However, in December last year a Federal Court judgment has laid bare the complex nature of Mr Gould and Mr Leaver's business interests in a $30 million tax case brought by the tax office and led to the judge referring the matter to the Commonwealth Director of Public Prosecutions, Federal Police and the Australian Securities & Investments Commission. Mr Gould and Mr Leaver are currently not subject to any criminal action and it is not known at this stage whether any charges will be brought against either man. The tax recovery processes are civil proceedings.

According to several well-placed sources, Mr Leaver co-owns a number of horses with various people including 4YO mare Gypsy Diamond and 3YO colt Woodbine, though it is not clear whether the entity that has had its assets frozen – Planette Thoroughbred Trading – is the owner of these horses.

Mr Jones, who has not been accused of any wrongdoing and is not subject to the freezing order himself, on Friday declined to elaborate on which horses he co-owned with Mr Leaver.

"I knew absolutely nothing about this until I received your email," Mr Jones said, adding: "I am in partnership with John Leaver, in race horses".

"I've just made a phone call and my understanding is that only the bank accounts have been frozen, so I don't understand how that can be represented as "asset freezing" he added.

The Federal Court orders pertaining to the "freezing of assets" of Planette Thoroughbred clearly state it applies to "all your assets whether or not they are in your name and whether they are solely or co-owned". A Westpac bank account held by Planette has also been frozen by the court.

High profile breeder, John Messara, chairman of Racing NSW and the successful Arrowfield Stud, confirmed his business also co-owned thoroughbreds with Mr Leaver. Mr Messara, who like Mr Jones is not subject to any court action by the ATO, declined to comment on whether any of the horses they co-owned were subject to the freezing order.

The freezing orders apply to the assets of John Leaver, Mirjana Leaver and Sophie Leaver. Mr Leaver's London-based daughter Kate – a social commentator who writes for popular online publications Mamamia, Huffington Post – is not subject to the freezing order. Fairfax Media could not reach either Sophie or Kate Leaver.

Mr Leaver's primary residence on the exclusive St Mervyn's Avenue in Point Piper is one of the properties frozen by the ATO. Land title records show Mr Leaver and Mirjana Leaver took out a $5 million mortgage over the property in 2001. A smaller house on the small cul-de-sac sold in 2013 for $17.3 million.

A plush terrace at 201 Sutherland Street, Paddington, is also subject to the order. Land title records show Sophie Leaver holds a $1.9 million mortgage over the house.

Details of the family's property on George Emery Lane in Glenquarry are scant and the Leavers did not answer the phone yesterday when Fairfax Media sought to contact them at the rural property. No information as to the value of the property or when the Leavers purchased it were available on the land titles.

Mr Leaver was the chairman of Gold Coast-based property developer Sunland between 1994 and 2005. He also previously sat on the board of listed investment house CVC Limited as did Mr Gould, though both men have since stepped down.