Tommy Hilfiger's Plaza penthouse
This 5,600-square-foot duplex in The Plaza hotel has been on and off the market since 2013, when fashion designer Tommy Hilfiger and his wife, Dee Ocleppo, first listed it for $80 million.
It was later dropped to $75 million, then to $68.95 million, and then to $58.9 million before it fell off the market in April. It's now back on the market for $50 million.
The condo is located on the 18th and 19th floors of the Plaza and has four bedrooms with views of Central Park and Fifth Avenue.
Trump's St. Martin chateau
President Donald Trump's luxurious St. Martin estate, which he owns through two companies called Excel Venture I LLC and Excel Venture Corp I, was listed for $28 million in May. It's also known as Château des Palmiers.
Its price was later brought down by a little more than $11 million, to $16.9 million, in August.
Trump typically uses the Caribbean escape as a rental property, and, according to the disclosure, he gets between $100,000 and $1 million a year from it. The sale is being handled by a revocable trust run by Donald Trump Jr. and Trump Organization executive Allen Weisselberg.
It reportedly survived Hurricane Irma relatively undamaged, in contrast to the widespread destruction that was brought to the rest of the island of St. Martin.
The Obamas' summer rental
President Obama and his family rented this sprawling, 7,000-square-foot mansion in Martha's Vineyard for an entire summer in 2013, but that seems not to have made the house any easier to sell.
Now it'll be just a little bit cheaper to live like the first family all year round. The house listed in July 2015 for $22.5 million. Just three months later, the house already had a 15% price chop.
Now, nearly two years later, the house is still for sale, at a discounted price of $17.75 million.
Alan Wilzig's toned-down Tribeca townhouse
Though not in a celebrity in the traditional sense, Alan Wilzig is an entrepreneur and semiprofessional race car driver who served as the real-life inspiration for a character in "The Wolf of Wall Street."
He's also been trying to sell his New York City townhouse for years. It's been on and off the market with different brokers and at different prices, initially listing for $44 million in 2014 and making its way down to $18.75 million in October.
The townhouse has looked progressively more tame as it's relisted over the years.
Michael Jordan's suburban Chicago property
Michael Jordan listed his Highland Park, Illinois home for nearly $29 million in 2012.
Five years later, multiple price chops have not helped it move off the market. It's currently for sale for about half that — $14.885 million.
There's a home theater, world-class workout room, and a massive set of gates bearing the number "23."
Steve Cohen's mansion in the sky
Billionaire hedge funder Steve Cohen has been seeking a buyer for his Manhattan duplex penthouse since 2013.
It's had a number of different listing prices: $115 million, $98 million, $82 million, $79 million, $72 million, $67.5 million, and now, $57.5 million.
The 9,000-square-foot space has five bedrooms and six baths. Cohen is an avid art collector, and the home has a dedicated gallery to put his pieces on display.
Matt Lauer's Sag Harbor estate
Matt Lauer is having a hard time offloading his home in the Hamptons. He originally listed for $17.995 million in July 2016. He cut $1 million from the listing price in September 2016, and now it's asking $14.9 million.
The 8,000-square-foot home sits on top of a 25-acre private lot. The home was built in a stunning traditional style with plenty of space for entertaining guests and a backyard pool to lay out by.
50 Cent's Connecticut mansion
50 Cent first listed his 50,000-square-foot home in Farmington, Connecticut, for $18.5 million in 2015. In the fall of that year, he lowered the price significantly, to $8.5 million, after he had filed for Chapter 11 bankruptcy.
He again lowered the price, this time to $5.995 million, in 2016, and the price has remained the same since.
The home is totally over the top, with "21 bedrooms, 25 bathrooms, an indoor pool and hot tub, a substantial night club, an indoor court, multiple game rooms, a green screen room, a recording studio," among many other opulent features, according to the Douglas Elliman listing.
