The Bayside family has bought the Woollahra pub, The Light Brigade Hotel, for about $9 million.
It comes two months after they sold the Newport Arms to Justin Hemmes.
"When we sold the Newport Arms, we did so knowing that it would not only serve as a chapter in our family's history in the hotel industry closing, but equally, would serve as a precursor to the next chapter; a new chapter," hotelier Kaine Bayfield told the Australian Financial Review.
Ray White Hotels' Andrew Jolliffe and Joel Fisher brokered the deal on behalf of Haritos Hotels ending an eight-year association with the hotel.