You Wynn some — and you lose some.

Casino mogul Steve Wynn is rolling the dice and relisting his Ritz-Carlton penthouse for $70 million. That’s after coming up craps when he tried to sell it two years ago in hopes of only recouping its purchase price.

Wynn also hopes for a wash on the West Coast, where his opulent Beverly Hills compound just went under contract for roughly $50 million, the same price he paid for it a decade ago.

The offloading efforts for the two properties came within days of each other at the end of June and represent massive progress for extravagances Wynn has tried to unload for years.

Both properties’ prices have jumped around like balls on a roulette wheel, with the California mansion priced as high as $135 million, followed by subsequent markdowns to the $50 million level.

Wynn bought the 27,000-square-foot, 11-bedroom California enclave, known as Villa Lulu, in 2015 for $47.9 million from Guess fashion co-founder Maurice Marciano. 

In New York, Wynn purchased the Ritz-Carlton duplex for $70 million in 2012, listed it for $90 million in December 2022, slashed the price to $65 million, then withdrew the listing in early 2024 before its current relisting at $70 million.

Regardless of whether the price has been a moving target or not, “The property is spectacular, based on its size and its views,” said Deborah Grubman of the Corcoran Group, which shares the New York property’s listing co-exclusively with Sotheby’s International Realty’s Serena Boardman.

The two-floor 50 Central Park South residence spans almost 11,000 square feet, or the size of a private plane hangar that can fit 1,500 people.

Its living room alone once served as the original hotel’s grand ballroom and now features 15-foot-high ceilings and 10 giant arched windows, five of which look out over Central Park. 

For all its size, the residence only has three bedrooms, massive ones to be sure, plus four full baths and two half baths.

The bedrooms are located downstairs in private quarters and are accessed via a sweeping marble staircase. The primary bedroom, which overlooks Central Park, has a spa-like marble bath, its own gym, a massage room and an enormous dressing room. The other two bedrooms feature generous views, while a staff room contains an ensuite bath and a laundry room. 

The aerie also contains a library and a media room, while an outside terrace stretches almost 45 feet along the length of the unit. 

The current $70 million ask for the property is the result of having “a serious seller and an appropriate price,” based on the home’s attributes and area comps, Grubman said.

Still, breaking even isn’t something the casino impressionado has been comfortable with before.

Wynn got his gaming chops not totally far from the Manhattan penthouse, in upstate Utica, N.Y., where he worked as a teenager at his father’s Lafayette Street bingo hall. The younger Wynn was on his way to Yale when his father died, and he took over the bingo business, which had grown along the East Coast. His father was a big gambler and Wynn also assumed his $350,000 in debts.

Wynn paid them off, and with money from the now profitable bingo halls and some borrowings, he headed to Las Vegas in the late 1960s where he, and probably Wayne Newton, became the public face of the gambling mecca.

While Wayne warbled, Wynn went to work, often horse-trading real estate with Howard Hughes and his estate to create luxurious properties and position them as lavish mega-resorts for high rollers and families.

Wynn demonstrated his affinity to dazzle early on. Starting with a small stake in the New Frontier Casino, where a bingo hall was installed, he went on to craft properties featuring a 54-foot volcano (the Mirage); full-sized ships battling with cannons (Treasure Island); and massive puppets, holograms, and a 40-foot waterfall (Wynn Las Vegas) as destination vacations.

Wynn saw his gaming empire crumble. He pulled out of the business in 2018 amid sexual misconduct accusations (claims that he has repeatedly denied) and resultant fines, an alleged payoff and lawsuits, and has been an active real estate investor since. 

Now 84 years old, Wynn is worth $3.9 billion according to Forbes, with hundreds of millions of dollars in residential properties.

For the New York penthouse, the $70 million ask only gets the buyer so far. There are $565,000 in annual carrying costs for tax payments and common fees.