The 30 acre hill top property Stella Nova was listed for
$59 million in 2019. After 4 price drops it sold for $20.6 million (per Zillow - only 35% of the list price).
Nile Niami originally hoped to sell "The One" for $500 million (video tour), but the unfinished property ended up at auction and despite drawing five bidders sold for "only" $141 million net of fees (against debt of $256 million). The buyer was self-made bllionaireRichard Saghian (paying only 28% of the original ask price).
The Mountain was originally marketed for $1 billion (Jeff Hyland declined to take the listing at that price) Despite a supposed bid of $400 million and rumored interest from the likes of Tom Cruise and Jeff Bezos, it failed to draw a buyer willing to take on the debt (reportedly ~$200 million) and reverted back to the Mark Hughes Trust. Vanity Fair's August 2022 article is a fascinating read of the long history.
Don Abbey reportedly purchased the entire 22 acreShelter Island in Montana (near Glacier National Park) for $1.76 million in 2000. After beginning construction it ran into cost overruns and lawsuits then took a decade to complete. Abbey listed it for $78 million, then $59 million, then $29 million. Then a $13.95 million price brought more attention, but it still took three years to sell in 2018 (the price was undisclosed). The state tax board apparently ruled that the property was worth $41.8 million in 2015 though Abbey claimed the island’s taxable worth was far less at $9.8 million (he may have been right). The 2014 tax bill for the property was $367,696. You can watch video of the property, which includes a helipad for year-round access.
Beverly Hills Sale-to-List price tends to average 95% or more, but at the top end of the market that's often not the case. 25 Most Expensive Listings Worldwide per Robbreport are recent listings that may or not sell for much lower than the original list prices.