Scarcely a year after he nabbed headlines by paying $8.2 million for an oceanfront home on Malibu’s Broad Beach, Ryan O’Connor is back making real estate waves once again. It’s all thanks to a very fortunate, highly lucrative deal the famously brash apparel entrepreneur scored; records show he’s quietly sold the Malibu house for $12.3 million — a whopping $4+ million profit before taxes and closing costs — to his next-door neighbor, billionaire private equity pasha Behdad Eghbali.
So O’Connor has taken his winnings and left Malibu, instead opting to shell out $13.6 million for something a little closer to L.A.’s heart, in this case a mansion set high above the Sunset Strip. The home’s modern, boxy architecture and charcoal grey exterior will provoke whiplashes, but the most impressive feature are the pools — yes, pools. Two of them, in fact, both infinity-edged with jetliner views of the Downtown L.A. styline and the Pacific Ocean.
Last sold in 2014 for $12 million to wildly wealthy window heiress Lori Milgard, the property completed a five-year renovation and expansion in 2020, resulting in the 5,000-square-foot contemporary seen here. It’s unlikely Milgard turned any sort of profit on the sale, and O’Connor scored the place at a giant discount — it was originally offered for as much as $19 million last year.
Like many homes in the tightly-packed Hollywood Hills, O’Connor’s swank new digs sit hard up on the street, with the attached two-car garage basically at curbside. Black metal front double doors given the place a sultry vibe and guard access to a brief atrium; just beyond is an all-glass door that pivots into the house itself.
