In the ultra-competitive housing market, buying a home can cause you to have to move fast. But on the flip side, selling your house is, most of the time, seemingly speedy. According to Zillow, in 2020 it took just 25 days on average to have a home go under contract in the U.S., and in certain months, nearly half of homes had an offer accepted on them within a week of them going to market. When you compare this to the amount of time that homes stayed on the market just a decade before (140 days, in 2010), it's clear that being a home-seller just keeps getting easier.

Unless you're a celebrity, that is. While the rich and famous can enjoy perks when it comes to homeownership that most of us can merely dream of (infinity pools, more space than a shopping mall, million-dollar views ... you get the gist), when it comes time to sell up, things can go awry. In certain cases, trying to sell a one-of-a-kind property can have its downsides, and some of the best-known names in the world have ended up with homes that they just can't get rid of. Let's take a look at some celebrity homes that nobody wanted to buy.

Christina Aguilera took three years to sell her Hollywood Hills pad

When Christina Aguilera bought her four-bedroom, seven-bathroom home in the Hollywood Hills back in April 2003 per Variety, she may well have thought she struck real estate gold; even though the home cost her a cool $5 million, such a desirable location and property is bound to appreciate, right?

Well, unfortunately, it wasn't to be. The 6,500-square-foot Steve Hermann-designed property — which boasted enviable views of the L.A. skyline, incredible indoor-outdoor living with the master bedroom adjoining the pool and outdoor space, and a home gym — should have been snapped up when she listed it for $7,995,000 in April 2008. But it quickly became apparent that even a "Genie in a Bottle" couldn't get the house to move for that price, and it would take at least another three years before Aguilera finally closed on a sale for the home. And when she did? It went for $4,653,815 — over $300,000 less than she paid for it originally. With a home like this, which included a home theater and 12-seat spa, it's difficult to understand why it wasn't snapped up sooner.

50 Cent's house sold for less than he bought it for

"Get Rich or Die Tryin'" might have been the motto of 50 Cent (real name Curtis James Jackson) at one point, but turns out it's easier said than done in some instances. Such was the case when it came to Jackson's property endeavors, which would make the hardiest real estate investor shudder. Jackson's Farmington, Connecticut property was bought in 2003 for $4.1 million from none other than Mike Tyson, according to The Wall Street Journal. The mansion, which stretched over 50,000 square feet, came with a frankly wild 19 bedrooms, 25 bathrooms, an indoor basketball court, a nightclub, and was decorated in an opulent white-and-wood style, per CNBC News.

Turns out, very few people need the kind of home that 50 Cent did, so he struggled to find a buyer when he first listed it in 2007 — and we mean struggled. In fact, it was such a struggle to shift it, that it took ... wait for it... 12 years until it finally sold. And when it finally changed hands, it was 84% less than its original listing price in 2007, at a final total of $2.9 million. 50 Cent, however, put the money from the sale to admirable use, with the proceeds from the sale going to the G-Unity Foundation, the rapper's non-profit.

Billy Joel tried to list his house at a massive price ... and it didn't work

When it comes to the sky-high prices of celebrity homes, it's easy to feel as though money's no object. But listing a property at the wrong price can affect people at any scale of the wealth spectrum, and legendary singer-songwriter Billy Joel learned this the hard way when he tried to sell his 13,000-square-foot Palm Beach County Mansion (per Town & Country).

The eight-bedroom, eight-bathroom Mediterranean-style property, with marble and onyx décor throughout and sweeping views of the Intracoastal, was bought for $11.8 million by Joel in 2014; when he relisted it a year later, he asked for an astronomical $29 million, according to the Daily Mail. No dice, unfortunately, and the singer had to reduce the asking price in 2016 by $2 million. However, that still wasn't quite enough, and Joel had to reduce the price again, and again, and again, ending up with an asking price of $16.9 million in 2018. Looks like money can buy you pretty much anything, but the one thing it can't buy is home buyers!

Frank Sinatra's old house has languished on the market for years

The most famous crooner on the planet, Frank Sinatra, had an impressive property portfolio to show for his work. Among Ol' Blue Eyes' homes was an Upper East Side penthouse (no doubt where he'd sing "New York, New York" while gazing out over the East River), an oceanfront home in New Jersey, and his most famous of all, the four-bedroom, seven-bathroom property he dubbed the "Sinatra House" in Palm Springs (per Elle).

But even Sinatra's legacy and star appeal aren't enough to shift one other property of his, his five-bedroom "Villa Maggio," designed by Sinatra himself and nestled in California's Coachella Valley. Over the years, Sinatra's former property has been listed countless times, dropping in asking price from $4,995,000 in November 2007, to $3,950,000 in September 2015, according to Realtor. And despite this home, which also comes with a tennis court, pool, and astonishing views of the California valleys, as of October 2021 it was still listed on the market, at a slightly higher price of $4,250,000 (via Berkshire Hathaway HomeServices).

Celine Dion built a waterpark in her home, and still couldn't sell it

Putting the words "Celine Dion" and "water park" together might not have been anyone's go-to, but when the Canadian singer began creating her own water paradise in Florida in 2010 per House Beautiful, the two things were linked forever. Dion's home, built with late husband René Angélil, was built on five acres of land bought for $7 million — and has not just a 20,000-square-foot, 13-bedroom, 14-bathroom Bahamian-inspired mansion, but a full-on water park. We're talking two water slides, two swimming pools, water cannons, a lazy river, and enough water to sink the Titanic (half a million gallons of it, in fact. Is that enough, actually? How big was the Tita- ... never mind, you get what we mean).

So this one-of-a-kind home, basically any kid's dream palace, should have surely been snapped up instantly when it was listed in 2013. But with an eye-watering asking price of $72 million, it all proved a little pricey for most people, and the property stayed on the market for a nightmarish four years before it finally sold in 2017. With a final selling price of $38.5 million, it was at almost half of the initial amount — but let's be real, that's still not a bad mark-up.

Keith Richards made a loss on his home sale

The legendary British rocker Keith Richards was clearly after a slice of New York luxury living when he purchased his Greenwich Village penthouse for $10.5 million in 2014, according to Forbes. The four-bedroom, four-bathroom home is located in the historic (and endlessly pricey) One Fifth Avenue, and the two-story duplex's luxurious décor more than matches its iconic location. The home matches bright white, airy interiors with plush furniture and pops of pop art throughout, creating a classy, chic home that also incorporated a cocktail den, the walls adorned with framed records, in true rocker fashion.

But buying a home in such a premium spot can mean that when it comes to selling up, things can get a bit complicated. Unfortunately, this is what Richards found when he and wife, Patti Hansen, listed the property in 2016 for $12.2 million. It all proved too much for potential buyers, and the penthouse would then languish on the market for a further two years, before selling for an ultimate loss on the original buying price, at $9.95 million. With a net worth of $500 million (yeah, no biggie, that's about how much we've got too), according to Celebrity Net Worth, we doubt that Richards was losing too much sleep. Still, he won't be getting no Satisfaction from losing out on half a million.

Steve Cohen's initial asking price was way too high

As a super-wealthy hedge fund manager and owner of the New York Mets, Steve Cohen knows a thing or two about a deal. Yet Cohen has been hounded not only by alleged complications in his professional life (via The New York Times), but also when it comes to his property acquisitions and attempts to sell them. This was the case back in 2013, when Cohen listed his ultra-luxury penthouse in midtown Manhattan for — wait for it – $115 million, according to Bloomberg. 

A glance at the property can tell us in part why the home entered the market at such a price. With a two-story living space that boasts floor-to-ceiling windows overlooking Manhattan and Central Park, and five bedrooms and six bathrooms in pretty much the best location in the city (East 58th Street), clearly Cohen was feeling confident.

Well, no dice. The penthouse would stay on the market for another eight excruciating years, finally finding a buyer in April 2021. And when it did, it had undergone a more than significant price cut, down to a final asking price of $29.5 million, over $85 million less than its initial cost. Sorry, Steve!

The Obamas' Martha's Vineyard property took years to shift

If you're like us, you may have wondered once or twice how the Obamas, one of the most famous and powerful families in the world, live their lives. Turns out, they like to unwind at Martha's Vineyard — and way before they bought their current vacation home, a seven-bedroom, eight-bathroom waterfront estate (per Town & Country) in 2021, they had another property in the area, a secluded 7,000-square-foot mansion, according to Insider.

However, when it came to selling this earlier home, not even the chance to own a piece of property that belonged to literal Barack and Michelle Obama could shift it. The estate, which came with its own infinity pool, a master suite with a private den, and luxurious bathrooms decked out entirely in marble (via Town & Country), was listed for $22.5 million in 2015 — towards the end of Obama's time in his permanent property, the little-known White House. Yet that all proved too much for buyers, and it would be another three years before the house finally sold in 2018, for a substantially lower amount of $15 million, to the Menemshovitz Realty Trust.

Michael Jordan's house proved impossible to sell

Michael Jordan may have been unstoppable on the basketball court, but his real estate woes are the stuff of legend for entirely different reasons. Jordan's Highland Park home is as iconic as his reputation: per Forbes, it's a 56,000-square-foot estate built in a secluded location with pure luxury oozing from every part of the home. Built over seven acres, the home contains (among other things) nine bedrooms, 15 bathrooms and four half baths, an indoor regulation-size basketball court (which should come as no surprise to anyone), a cigar room, a wine cellar, a forest preserve, and gates with his famous No. 23 adorned across them.

Yet herein lies the problem: According to Forbes, the sale of the property came up against difficulty due to the hyper-customized nature of the home (to Jordan's remarkable endeavors and career achievements). Add to that the enormous size of the property and difficulty in maintaining it, and buyers are few and far between — so much so that after listing it for the first time for $29 million in 2012, in 2020 it was back on the market for $14.9 million, almost half the price.

Pierce Brosnan's house was taken off the market again after a year

Former "James Bond" Pierce Brosnan surely developed a taste for the finer things in life during his stint as the world's most famous secret agent. But does the rest of the general population share his taste? This was the trouble he came up against when he tried to shift his Malibu home back in September 2020, according to the New York Post, for a stomach-churning $100 million. A year later and with no buyer in sight, Brosnan had to take his property back off the market, without any reduction in price tag.

Taking a look at the property, we can certainly see why Brosnan thought it could score that amount. The oceanfront home is frankly gorgeous, created in a Southeast Asian-inspired aesthetic with floor-to-ceiling windows highlighting both the incredible water views and the grounds of the property, including a saltwater pool, a fire pit, and a private beach path. The main house (dubbed the "Orchid House") has almost 12,500 square feet of space, and in combination with the guest house, there are five bedrooms and 14 bathrooms to choose from. Might just be a little pricey for most.

Sean Combs' house took four years to sell

Sean Combs knows more than a little about getting people to buy things, with an empire that's worth $900 million and includes the Ciroc vodka brand (per Celebrity Net Worth). Regrettably though, master of rebranding Combs (also known as P. Diddy, Diddy, Puff Daddy, and Puffy) couldn't translate this ability to the sales of his own Park Imperial property, which he originally listed in 2012 for $8.5 million, according to Curbed New York. The luxury three-bedroom apartment, which came with grand views of the city, its own media room, and a bathroom-turned-wet-bar, was originally bought for $3.82 million back in 2005, but selling it was another story.

In fact, it took four years of headaches and renegotiations of the price before Combs finally sold the property in 2017, states The Wall Street Journal. When it went, it was for substantially less than he listed it for originally, at $5.7 million. One saving grace? It was an all-cash deal. We guess things could be worse!

Sylvester Stallone's house was on and off the market for a decade

With his decades-long Hollywood reputation, you might expect Sylvester Stallone's properties to be snapped up instantly by those who want a slice of his history when they go on sale. In truth, it hasn't quite turned out that way for the "Rocky" star, who's had a long and difficult history with trying to sell one of his properties, a La Quinta home set in the exclusive Madison Club gated community, according to Dirt.

The Mediterranean-inspired home, which offers nearly 4,900 square feet of space, two master suites (one with its own wet bar), and an outdoor kitchen, was acquired in 2010 by Stallone for $4.5 million. Yet just a year later, it was back on the market — and continued to be, on and off, for almost a decade. In 2020, the property went back to sale again, this time with a price of $3.35 million, far less than Stallone had paid for it years before, in what's undoubtedly a bit of a hit for the star. Elsewhere, Stallone also reduced the price on another of his properties for sale, a mansion in L.A., dropping from $110 million to $85 million in 2021, according to Insider.

Jennifer Lopez's house had to be reduced by $10 million

"Love Don't Cost A Thing," sang Jennifer Lopez once upon a time — but as her potential house buyers have found, property can sometimes Cost A Little Too Much. This was the issue when J. Lo called time on her Hidden Hills Estate property, which she originally bought for $8.2 million back in 2010, according to Variety. The over-17,000-square-foot mansion, which contains nine bedrooms and 12 bathrooms, also included its own two-story entertainment wing with an enclosed staff apartment, a 20-seat theater, a professional recording studio, and two walk-in closets in the master suite.

But all the commodities in the world couldn't seem to justify Lopez's original asking price when she listed it in January 2015 at $17.5 million — and buyers balked, leaving the property on the market for two long years. When the home finally sold, it was for a far more modest $10 million — $7.5 million lower than her original intended sale point. It's worth pointing out that J. Lo still made a profit on the house, but that's still gotta smart a little.

Jeff Bridges ended up with half his original asking price

One wouldn't expect the King of Cool Jeff Bridges to be rattled by something like property sales, but even he must have felt a bit unsettled by the amount of time it took to sell his Montecito home — two years, in fact, according to Architectural Digest. The stunning property was bought for just under $7 million back in 1994 (per the Los Angeles Times), and had originally been listed for resale for a whopping $29.5 million. However, that all proved a little too much for buyers, and when the home finally did change hands in 2017, it was for a decidedly more modest $15.925 million, around half of the original asking price.

The plus side for the buyer is that they gained a home for a clear bargain that is positively gorgeous. With once-in-a-lifetime views of the Montecito foothills, the villa-inspired property contains vaulted ceilings throughout, décor which combines wood, stone, and antique effects with modern furnishings, a master suite with its own fireplace, and lush greenery surrounding the home. Bridges also seems to have a bit of a claim on the Montecito market, too; in 2019, he sold another Montecito home, to none other than Oprah Winfrey, according to the Los Angeles Times. If you folks ever need a housesitter, you know where we are!