The Wellington-based company's recent annual report showed the Drury family were the software company's largest single investor with 17.7 million shares or 12.58 per cent of the company.
Drury quit as chief executive and separated from his wife Anna last year. He remains on the company's board as a non-executive director.
A recent run-up in Xero's share price, giving it a market cap of $9.1b, has made the Drury family billionaires on paper.
The share sale revealed today was Drury family's largest.
Its major payday was in November 2017 when it sold shares worth $95 million.
Xero shares jumped more than 10 per cent last week after it reported its first cashflow positive result and a maiden net profit in the second half.
For its year to March 31, the ASX-listed, NZ-headquartered cloud-accounting company posted a net loss that expanded to $27.1 million from the year-ago $24.9m.
But beneath the headline loss were some numbers that got investors pumped.
Xero had positive free cash inflow for the first time of $6.45m, 1.2 per cent of revenue, in the year compared with a $28.5m outflow the previous year.
And in the second half of the year it made a net profit of $1.4m - the first time the company had been in the black since it was founded by Rod Drury back in 2006.
Revenue jumped 36 per cent to $552m.
Subscribers rose from 1.37m to 1.82m, a 31 per cent increase.
Craigs Investment Partners deputy head of institutional research Stephen Ridgewell had a more measured approach to the result. He called it "solid" but also noted that Xero's free cashflow forecast - the only guidance metric that could be eked out of the company today - was, at around $9m for 2020, only a third of the analyst consensus.
Ridgewell had a hold rating on the stock based on valuation.
