#13: The Glamorous Halston Penthouse

The asking price: $38 million, lowered to $21 million

What it was bought for: $18 million

The Halston Penthouse, once the epicenter of glittering soirées attended by icons like Liza Minnelli and Andy Warhol, now faces a quieter chapter. Listed in 2011 with a jaw-dropping $38 million price tag, this architectural masterpiece has seen its asking price tumble to $21 million after years of lingering on the market.

Despite its storied past and striking design, including dramatic 32-foot ceilings and a sunken living room bathed in natural light, the legendary home struggled to captivate modern buyers until fashion designer Tom Ford purchased it in 2018 for $18 million.