The top sale at weekend auctions was a North Bondi penthouse within the former site of Blue Water Grill restaurant.
It sold under the hammer for $4.02 million.
It last sold for $5.75 million in 2006 when bought by the horse breeder Dean Fleming's family. The $1.73 million loss equated to 5% decline annually during its six-year ownership.
The three-bedroom apartment is one of six in the Ramsgate Avenue block.
The block's last ominous sale was $1,785,000 for a three bedroom 189 square metre apartment that fetched $2.15 million in 2007.
The North Bondi penthouse offering had about 110 square metres of internal space plus 164 square metres of outdoor decking.
It was listed as now with a family of five, the Flemings are moving to something bigger.
Pre-auction he suggested he was realistic when it came to price with the McGrath agents Di Baker and James Dack giving the price guide as "between $4 million and $6 million".
"That's the market. You've got to meet it," Fleming told Fairfax Media after the weekend auction.
"It's disappointing, but it's time to move on."
A buyer from Melbourne secured the property with just one bid over the telephone.
Sydney recorded a 60.3% weekend clearance rate, according to Australian Property Monitors.
In Melbourne there was a clearance rate of 60% compared with 59% last weekend and 51% for the same weekend last year, according to Enzo Raimondo at the Real Estate Institute of Vicoria.