An accountant who committed “industrial scale dishonesty” to fund an extravagant lifestyle has been jailed for 11 years and five months.

Stephen Day, 51, plundered more than £1 million from several companies, defrauded three NHS organisations he secretly worked for at the same time, and targeted a female friend in a romance fraud despite being in separate relationships with two men.

The judge who sentenced him at Leeds Crown Court on Thursday told him “there was no boundary of dishonesty that you were not prepared to cross” as he tried to evade detection at various points by falsely claiming he had cancer.

Day purchased several properties in Scotland, including a 45-acre estate which had its own salmon fishing area on the River Annan, and is it thought another development in South Africa to let out as a holiday rental, according to investigating detectives.

His ill-gotten gains funded a taste for luxury holidays, expensive furniture, car accessories and his love interests, neither of whom knew of the other, the court heard.

Day, of Quiech Mill, Blairgowrie, who previously lived in Aberford, Leeds, used his status to be appointed as director, financial director or company secretary of four organisations including a care home provider for vulnerable people and the management company of the block of flats where he lived in Manchester city centre.

Once in place he sought to empty their bank accounts into his own and hide the trail with false ledger accounts and documents.

After he took over the accounts at Asia House in Manchester, where he owned a flat, he faked a bank mandate which give him unfettered access to money belonging to members of the residents’ association.

Another victim was Gloucester-based Avida Care, where he became the financial director and took on the responsibility for payroll and support services. When he failed to attend meetings and provide financial information he lied that his mother had died and he had been diagnosed with cancer.

Day also admitted fraud by misrepresentation as he failed to disclose to three NHS trusts that he was working full-time for them all at the same time on a combined daily £2,000 salary, on top of his other interests.

The defendant resorted to more lies as he struggled to meet all his commitments by again claiming he had cancer, had been involved in car crashes and was mourning the loss of his father, who had actually died nine years earlier.

In short you have caused misery, hardship and anxiety to many. This was industrial scale dishonesty purely to fulfil your own greed

His deception cost Merseyside Commissioning Support Unit, South East Staffordshire and Seisdon Peninsula Clinical Commissioning Group and Cheshire and Wirral Partnership Trust a total of about £88,000.

Judge Simon Batiste said his most cynical fraud was committed on a female friend who he had met again many years later through a professional networking site.

Day said he had been widowed two years earlier and went on to her groom her as he concocted reasons to borrow more than £4,500 from her as his financial dealings caught up with him.

The judge said: “There was no boundary of dishonesty that you were not prepared to cross. The consequences have been enormous both financially and in other respects, including businesses losing viability and being wound up, people losing their jobs, reputational damage, loss of credit rating and people being unable to sell their homes.

“In short you have caused misery, hardship and anxiety to many.

“This was industrial scale dishonesty purely to fulfil your own greed.”

Day, who pleaded guilty to 12 counts of fraud and theft totalling nearly £1.4 million between 2012 and 2015, was also disqualified from being a director for nine years.

Following sentencing, Detective Sergeant Stephen Donohue, from Greater Manchester Police’s specialist fraud investigation team, said: “Although the investigation has now closed, our work does not stop here and we will now look at a proceeds of crime hearing to try and recoup some of the funds he stole, to recompense his numerous victims.”