High-profile barrister Charles Waterstreet will consider declaring himself bankrupt after he was ordered to pay more than $420,000 to the Tax Office in a long-running dispute over unpaid income tax.

Waterstreet, 67, was ordered on Wednesday to pay $420,456.21 and costs after a District Court judge found he failed to pay income tax in the financial years of 2012, 2013, 2014 and 2015, and did not pay subsequent penalties issued for failure to pay on time.

Barrister Charles Waterstreet has been ordered to pay more than $420,000 to the Tax Office. Credit:Ben Rushton

In court documents, Waterstreet denied some of the allegations levelled against him by the Deputy Commissioner of Taxation and said he could "neither confirm nor deny" others.

Judge Judith Gibson said Waterstreet had not offered a "substantive" defence to the allegations, adding some of his denials were "contradictory" and "not supported by any evidence".