David FitzPatrick bought the $1.265m (€978,000) apartment a day after the last government's bank guarantee in 2008.
Newly filed documents show he sold the apartment on March 16 this year for $951,000, (€734,900), a loss equivalent to €242,000 on what he paid for it.
It is understood the proceeds of the sale were used to pay back borrowings to Anglo, now called the Irish Bank Resolution Corporation.
Documents seen by the Irish Independent reveal how Mr FitzPatrick (31) used the property as collateral to borrow $50,000 (€38,500) from Anglo -- drawing from an €87m secret loan facility the FitzPatrick family had with the failed bank.
Papers in the New York Land Registry show that, up until May 2009, Mr FitzPatrick had been afforded a $1.257m (€968,900) line of credit by the bank from the €87m FitzPatrick loan facility.
The sale of the apartment took place just weeks before Mr FitzPatrick's marriage last month to solicitor Barbara Clear, a niece of K Club owner Michael Smurfit.
He is now understood to be renting another luxury apartment elsewhere in Manhattan, in a building with views of the Statue of Liberty.
Mr FitzPatrick was employed in the New York office of Anglo. However, staff at the office said last night that he had not worked there for two years.
He bought the apartment in the trendy East Village district on October 1, 2008, a day after the Fianna Fail/ Green Party government bailed out his father's ailing bank as part of its €400bn bank guarantee, which covered the country's six main banks, including Anglo.
Less than three months later, on December 18, Sean FitzPatrick resigned as Anglo chairman and admitted for the first time that he had hidden €87m in secret loans from shareholders by shifting the loans around.
A day later, his successor David Drumm quit as chief executive -- two days before the government pumped €1.5bn into Anglo.
In January, after four tumultuous months, the Government was forced to recall the Dail from its Christmas break and nationalise Anglo Irish.
A day after the announcement of the guarantee, Mr FitzPatrick paid $1.265m for the "mint condition" one-bedroom apartment in Manhattan, which included a fully fitted kitchen and hardwood floors. The property also has a "private landscaped roof deck" reached via a spiral staircase from the living room.
Eight months later, papers filed with the New York Land Registry show that he secured a $50,000 (€39,000) mortgage on the property from Anglo Irish Bank, dipping into an €87m credit allowance set aside for the FitzPatrick family.
This facility is understood to be the same €87m in secret loans that Sean FitzPatrick controversially transferred to another institution, Irish Nationwide, in an effort to hide the extent of Anglo's loans to its directors. Deeds to the property show that New York real estate agent Cindy Scholz snapped up the apparent bargain when Mr FitzPatrick sold it, though last night she declined to comment on the purchase.
Meanwhile, the documents also list Mr FitzPatrick's new address as an apartment in the One West Street development known as Ocean Luxury Residences, a skyscraper block of apartments beside Battery Park.
Monthly rent on one-bedroom apartments start at $2,995 (€2,300), while two-bedroom flats start at $4,295 (€3,300).
The sales blurb for the condominium promises that "the moment you enter, you're transported to a 14th Century Venetian Palace".
Amenities on offer to residents include a "state-of-art fitness centre", "complimentary Sunday brunch" and use of a roof for "sunset gazing, entertainment, or simply relaxing".
Mr FitzPatrick's wedding to solicitor Barbara Clear in April had a strong New York theme.
Tables at the K Club, where they held their reception, were named after Big Apple landmarks. Mr FitzPatrick is reported to have proposed to his wife in the city. The couple chose New York department store Bloomingdales for their wedding gift wish list, which included items such as Waterford Crystal champagne flutes.
Attempts to contact Mr FitzPatrick about the sale of his apartment were unsuccessful last night.