More than 20 adults and children living in three Dublin properties have been given to the end of January to vacate the premises.
Ms Justice Leonie Reynolds made orders granting Galway-based credit management firm Everyday Finance DAC various orders requiring the residents to vacate and hand over possession of three properties located at Fairview Avenue in Dublin.
The properties were acquired by Everyday earlier this year when it bought loans used to buy the three houses and originally taken out by businessman Jerry Beades with PTSB in 2002.
However following lengthy legal proceedings involving it and its predecessors in title Everyday claimed it had been unable to obtain possession of the properties, and that the occupants would not co-operate.
The judge said she did not accept an argument advanced by some of the residents that they had valid leases in respect of the properties, for which €2.4m remains due and owing.
A stay was placed on the order to January 31 next.
The judge also refused an application by two of the residents Tomasz and Marta Skorupinska, who have two small children to adjourn the matter.
They wanted additional time to get lawyers to represent them.
The Judge refused that application on the basis they had previously had solicitors on record to advise and represent them for several months and had months to obtain new ones since discharging their previously legal representatives.
The Judge said that on reading recent sworn statements on behalf of the couple that it appeared they "had help" with the documents.
The judge said she was not prepared to allow any more delays in the case and told the couple that "time has run out".
In her ruling the Judge said possession orders in respect of the properties had been before the courts since 2012.
The Court heard the properties were acquired by businessman Jerry Beades in 2002, who it was claimed had borrowed €1.7m from PTSB in 2002.
Proceedings were brought following an alleged default on repayment of the loan.
The loans were acquired by a fund called Cheldon Property Finance in 2015.
An order for possession of the properties against Mr Beades was confirmed following a decision by the Supreme Court in 2016.
Earlier this year Cheldon obtained orders allowing it to execute the possession order.
It was unable to obtain possession and returned to the High Court.
Following a hearing in July Mr Beades, who has appeals before the Court of Appeal in regards to the possession orders, and his former spouse Brid Kavanagh, who had claimed an interest in the properties, gave undertakings.
These include that they would not impede Everyday, which took over the loans from Cheldon last April, in its efforts to take possession of the properties.
Proceedings were brought over the resident's occupation of the properties. Everyday claimed that the residents were present without a valid lease.
Everyday, represented by Mr Stephen Byrne Bl, said the residents had claimed they had a lease in regards to the properties, where they claims to have lived for several years.
However, no lease had ever been put to or sanctioned by the lender, or the parties that subsequent acquired the loans and was therefore invalid.
His client had attempted to negotiate with the residents and said they were unable to inspect the properties.
Last July when the matter first came before the court counsel said Everyday was prepared to allow the residents stay-on in the properties rent-free for several months so they could save enough for a deposit on new accommodation.
Counsel said the offer was not accepted. Counsel said the residents had not co-operated with it or its predecessors in title and because it's agents were not allowed to inspect the properties it had concerns about their condition.
The couple had argued that no consideration had been given to them, and said that Everyday's offer was unacceptable.