Jeff Bridges became well-known for his laidback portrayal of The Dude in The Big Lebowski, and his Montecito home appears to have been influenced by that particular character. With a sunken living room, almost floor-to-ceiling windows, and a terrace, there was a lot of light and peace to be found. Plus, the added privacy of the 19.5 acres the home sat on. Including a meditation room, recording studio, pool, two guest houses, fruit orchards, hiking trails, and vineyards, it’s surprising that Bridges’ listing sat on the market for two years before selling in 2017 for $16 million.
You’d think a man as famous as Frank Sinatra would attract some interest, but the singer’s previous home was put on the market for just under $5 million and didn’t get a single bite. Villa Maggio, located just outside of Palm Deserts and overlooking Palm Springs, seemed to struggle despite the home’s beautiful surroundings and interior. The home was listed on and off for 15 years without getting a sale. Sinatra himself commissioned Villa Maggio in 1967 and created a true getaway for himself, his family, and his guests. The main house has 5 bedrooms and the guest house has 3. There’s a pool and pool house on the property as well as a tennis court and helipad. After several price drops, the listing appeared back on the market in 2021 for $4.25 million. It looks like this home will need a buyer who appreciates remote areas and cinema history.
Matt Lauer drew the wrong kind of attention in 2017 after complaints of inappropriate behavior, and unfortunately, his reputation might have been the cause for the lack of interest in his Sag Harbor home. Spanning 14,000 square feet, the home sits on just over six acres near the Peconic River and includes two guest houses as well as a tea house. It’s an area designed for privacy, but the estate itself seems bare. Lauer initially listed the 12 bed, 12 bath estate for $44.8 million in June 2019, and took a huge loss when it recently sold for $33.8 million.
Christina Aguilera listed her Hollywood Hills home in April 2008 for just under $8 million. She purchased it five years earlier for $5 million and, though it eventually sold, the singer had to accept a loss. The 6,500 square foot home was a Steve Hermann design, with views of the LA skyline and both indoor and outdoor living areas. Despite including a pool, spa, theater, and home gym, the listing languished for three years and eventually sold for $4.6 million; less than she paid for it. At this point, with two homes of very different styles lingering on the market, the singer herself seems to be the common denominator.
Bruce Willis is a well-loved actor with a net worth of $250 million. He’s played a myriad of characters, but remains a stoic man in the public eye. His Spanish-style Beverly Hills mansion, built in 1929, may be understated compared to the luxurious abodes of other actors, but appeared tasteful. A large wooden deck, tennis court, and acres of open spaces created an attractive and peaceful space. However, the home sat on the market for over a year before it finally sold in 2014 for $16.5 million.
Tommy Hilfiger, fashion designer and namesake of his founding company, put his Manhattan penthouse up for sale after a decade of owning it. However Hilfiger’s tastes as a designer might be what kept the penthouse on the market for several years. Originally two separate apartments, Hilfiger and his wife purchased the spaces in 2008 and joined them for a total 6,000 square feet. The twelve rooms include hand-painted murals, domed ceilings, dark walls, and a custom-paneled office. The penthouse was originally listed for $80 million but accepted an offer of $31.2 million.
Calvin Klein, the well-known fashion designer, owned a beachfront bungalow in Miami, Florida that buyers just weren’t interested in. While Klein has made a name for himself as a designer, his fashion sense doesn’t seem to have translated to home interiors. The home was covered in white-washed wood that may have appeared outdated to potential buyers, and it sat for two years before finally selling for a lowly $12.8 million.
While some celebrity homes may be understated to the point of being boring, others are just too much. Ryan Seacrest’s estate in Beverly Hills seems to have scared buyers away with just how luxurious it is. Originally listed in 2020 for $85 million, the high price tag came with a three-acre property, seven bedrooms, ten bathrooms, two guesthouses, a pool house, a wet bar, a wellness center, a therapy room, and more. The home was also previously owned by Ellen DeGeneres and is reportedly one of the most costly in the area. There’s a long list of other inclusions that may have been just too much. After all, not everyone is attracted to excess. Seacrest lowered the price to $74.5 million in August 2021 and it hasn’t moved since.
Demi Lovato tried to unload her Laurel Canyon mansion only months after suffering a reported overdose at the location. It was originally listed for $9.5 million. With four bedrooms and seven bathrooms, it’s not clear what exactly kept buyers from taking an interest.
Considering their popularity, you would think any home listed by Barack and Michelle Obama would be snapped up in a heartbeat. However, their Martha’s Vineyard home – listed in 2015 for $22.5 million – stayed listed for three years before selling for $15 million in 2018. It’s unclear what was driving buyers away from this particular listing, as the area is secluded, the house is a reasonable size at 7,000 square feet, and upgrades include an infinity pool, marble bathrooms, and a master suite. Obama was still in office and in residence at the White House when this home went on the market, but his tenure as President didn’t help boost interest in this property.
In December 2018 Rihanna listed her Hollywood Hills home for $7.3 million. The gated .44-acre property is in a desirable neighborhood (Mount Olympus) and the home itself is just over 7,000 square feet. But several outlets noted that Rihanna’s aesthetic was all over the place in putting this abode together. That’s not too surprising considering how she’s grown as an artist, but it made for a confusing and inconsistent design. Frosted glass railings, herringbone floors, and dark brown cabinetry clash noticeably in the photos. In October 2021, the price was cut and it finally sold in 2022 for just $6.8 million; a loss for the singer.
Pierce Brosnan, best known for his portrayal of 007, listed his Malibu mansion in September 2020 and took it down a year later when it wasn’t selling. The original listing price was $100 million; pretty steep for the market, but Brosnan and his wife commissioned the property themselves. It took just over a decade to complete. The home was just over 12,000 square feet and featured five bedrooms and fourteen bathrooms. Other features include a movie theater, guesthouse, saunas, steam room, Japanese soaking tub, recording studio, and more. The photos show a light-filled, open space in almost every room, as well as an attractive outdoor area. It’s unclear why the house never sold, but Brosnan apparently wasn’t willing to drop the price and it hasn’t shown up on the market since.
For her second appearance on our list, Christina Aguilera took another loss for the home she purchased from Ozzy and Sharon Osbourne. The Spanish-style mansion made an appearance with the Osbournes on MTV Cribs and apparently, Aguilera liked what she saw. Some outlets labeled the décor “garish” and photos show an excess of red velvet and overdone chandeliers. Buyers viewing the home would have had to look past piles of cheesy furniture and clashing paint colors. The 10,000-square-foot mansion finally sold after two years on the market for $11.5 million – $2 million less than what she originally listed it for.
If you weren’t already aware, Dwayne “The Rock” Johnson is a horse lover, as proven by the 45-acre estate in Powder Springs, Georgia where he lived for several years. Photos of the empty home show a clean slate, beautifully utilizing both stone and wood in muted colors. It’s classy and a little old-school with a smaller but interestingly shaped pool out back along with outdoor living spaces and fireplaces. The Rock bought the property for roughly $9 million in 2019 and had it back up on the market in just a few short years. In January 2021 he listed it for $7.5 million, acknowledging that he’d be taking a loss on the property. Other equestrians with the right wallet will be happy to gain from his loss, as the property includes a 12-stall barn, riding arena, and viewing deck.
With a net worth of $800 million and a staggering amount of accolades across her career, Celine Dion cuts an intimidating figure; maybe that’s why her Florida mansion took four years to sell. At first glance, the aerial photos are a bit cringe…unless you really love water slides. A resort-style pool area – literally massive – takes up a stunning portion of the acreage, complete with a water slide and bridge. Three of the swimming pools utilize geothermal heat, a tennis court, a golf range simulator, an outdoor kitchen, and cabanas complete the feeling of overkill. Dion purchased the home for just over $7 million in 2008 and listed it for a jaw-dropping $72.5 million in 2013. It sat for four years with one price drop before selling in April for $28 million.
Jason Biggs has repeatedly played funny, sweet guys in quite a few movies, and he brings a sense of nostalgia to his fans. Biggs’ family home in LA seemed a perfect fit for the actor, with its contemporary style and cozy, minimalist interior. The 2,700 square foot home came with three bedrooms and four baths with dark wood floors and walls of windows. Despite the small property – only .2 acres – the views and private drive were definitely a selling point. However, Biggs’ home was on and off the market for almost a year, eventually selling for $2.56 million. Biggs himself moved on to larger homes that, thankfully, sold quicker when the time came. It’s unclear what held his Sunset Strips contemporary back.
Shakira, the Colombia singer often referred to as the “Queen of Latin Music,” has made the news more recently for financial troubles as she battles accusations of tax fraud. Unfortunately for Shakira, fame doesn’t always bring smooth sailing, and she struggled for years to offload this property. The beach house, located in Miami, was first listed in December 2013. It seemed reasonably priced for the area and photos show a clean, crisp, minimalist mini-mansion; not too extravagant, but definitely tasteful. With six bedrooms, a pool, water frontage, and a dock, for whatever reason buyers avoided this home until it finally sold in 2021 for just over $11.5 million. Maybe the minimalist approach was actually too little for the Miami market.
When it comes to Sonja Morgan’s townhouse, some people might picture a classy, upscale place for the Real Housewives star to spend her time on the Upper East Side. Unfortunately for Sonja, this wasn’t a good buy – it’s pretty confusing what made her purchase the home in the first place, as one glance at the outside makes it obvious why no one has put in an offer yet. Sonja’s neighbor is a twenty-story condo complex and to make things worse, her townhouse abuts the complex’s parking garage. Step outside and there’s a gaping two-car entrance only feet away. Inside the five-story home is light, airy, and charming, with classy chandeliers, fireplaces, and a backyard garden. But it doesn’t look like Sonja will be selling this place anytime soon – at least not for the $8.7 million she recently re-listed for.
Apparently, Bruce Willis is no stranger to selling failures. Bruce Willis struggled to sell his Bedford mansion, just an hour north of Manhattan. Many people dream of living in the country with city access, but for whatever reason, buyers snubbed Willis’ digs for almost a year before it finally sold. Bruce and his wife Emma Heming listed the home for $12.95 million as they looked to shift to California. The Bedford property held four buildings, including the main house of 9,000 square feet, and has been described as “scenic.” The 22.6-acre property guarantees privacy, but may have deterred city clients with its wide open spaces. Eventually, the Bedford mansion sold for $7.66 million.
50 Cent – real name Curtis James Jackson – is a man not only of gold grills, but a gold heart. When he finally sold his Farmington, Connecticut home for $2.9 million, it was at a loss – but he put that $2.9 million toward his non-profit, G-Unity. Jackson bought the property in 2003 for just over $4 million from Mike Tyson. The over 50,000 square foot(!) mansion included nineteen bedrooms and twenty-five bathrooms and was done up in a clean white-and-wood combo. However, it definitely had some character distinct to the rapper, with a nightclub and indoor basketball court included. The home was listed in 2007 and spent a grueling twelve years on the market before eventually selling.
Mary J. Blige is an impressive woman – she’s a singer, songwriter and actress often referred to as the “Queen of Hip-Hop Soul.” But when her New Jersey home was listed in August of 2019, a big red flag was raised right away: there were no photos with the listing. Any homebuyer knows that a lack of photos means there’s a problem somewhere, although it’s hard to figure out just why the Queen tried to get away with only a write-up of the property. Her agent noted that a gym, office, and three fireplaces were included in the home, but there’s not much else said. Blige reportedly had the property on and off the market for almost a decade, and it eventually sold for $5.5 million. It was a huge loss for the singer-songwriter as she’d purchased it in 2008 for $12.3 million. Makes you wonder what happened to the home for the price to drop so drastically…
Keith Richards, of the Rolling Stones, owned a Greenwich Village apartment in a popular area that bounced on and off the market for two years. With four bedrooms and four baths in a 2,700 square foot area, the apartment was listed by Richards and his wife for just over $12 million. Each room was full of symmetry, color, and minimalist design. Overall, Richards managed to walk the line between interesting and outright strange. Buyers drawn to art deco vibes should’ve been flocking to the area, but the apartment sat before eventually selling for $9 million – a loss for the rocker.
Sylvester Stallone shows up once again with his La Quinta home appearing on the list this time. Several parties call this retreat “stunning,” but Stallone took a hit when it finally sold in 2020. He accepted an offer of just over $3 million – more than $1 million less than he paid for it. The wood-and-stone design of the home is a great fit for its desert surroundings. For whatever reason, it came on and off the market for years before finally selling. With a barbeque, spa, and man-made creek, it’s hard to understand why no one was clamoring to get their hands on a Stallone property. Can’t win them all.
If you were asked to picture the home of Burt Reynolds when he was at the height of his career, you probably wouldn’t be too far off from the property that was sold in 2015. Unfortunately for Burt, it went into a foreclosure sale for $3.3 million. With wall-to-wall carpeting and mirrored walls, there’s a lot of cringe in the design that added age in a bad way. Almost all of the listing photos show a very dated home with dated furnishings included. But someone saw potential and eventually snapped up the Florida home.
Spears has had her ups and downs over the years, and unfortunately her Beverly Hills mansion was part of the trouble. Britney paid $6.75 million for the home in January 2007 and listed it only months later for $7.5 million. This was immediately after her very public breakdown, so there was a lot of speculation in the media. The Spanish style mansion and property has stunning views, a movie theater, outdoor BBQ area, plunge pool, maid quarters and more. Her interior designer did an amazing job balancing opulence with moderation and each room is tasteful, but rich. Things started looking up for the popstar and in 2021, she finally accepted an offer of just over $4 million. A loss, but she’s likely happy to be rid of this burden.
Kid Rock is notorious for partying, often appearing around town or in music videos in chill attire: hats and sunglasses. His colonial-style home in Detroit was very…specific. With dormers and colonnades, the design itself was interesting. But perhaps the colonial look didn’t pair well with Kid’s love of water-related hang time. The property included a private boathouse, roof deck, and Jet Ski lifts. There was also a house-wide patriotic theme, complete with eagles and spangled decorations, which came with the home. It was an odd combination of furnishings and amenities, to say the least. The 6,000-square-foot mansion eventually sold for a little over $2 million. For whatever reason, the new owners kept every inch of the rock star’s pad exactly as-is.
A home owned by Tom Cruise could be either classy or crazy. It’s hard to tell with the Mission Impossible star which side you’re likely to get. But the estate located in Colorado seems to reveal another side of Cruise. Decked out in fine wood and comforting living areas, it manages to feel both cozy and stately at the same time. A vast wilderness landscape waits right outside almost floor-to-ceiling windows. Cruise listed the home for $59 million in 2014; a steep price, but lovers of the outdoors might have thrown a few looks its way due to the beautiful surroundings. When it didn’t sell, Cruise removed the listing and ended up re-listing in March 2021. It finally sold two months later for $39 million; less than he was hoping for.
Donald Trump has gone from entrepreneur to celebrity to US President, but still can’t seem to sell his St. Martin chateau. Originally listed in 2017 for $28 million, the home is still on the market. The words “lavish” and “sumptuous” have been used to describe the main home and connecting villas, one of which is used for staff. Amazingly, the buildings and surrounding land have withstood literal hurricanes and come out almost unscathed. According to sources, Trump has been using the property as a rental and doesn’t spend much time down there himself. Apparently he no longer sees it as a viable income source or worth his time. Thus the recent price drop to $15.5 million.
Erika Jayne, the reality star known for her antics on Real Housewives, has been caught up in ongoing bankruptcy proceedings after her split with husband Thomas Girardi. The home owned by the two (purchased by Girardi in 1980 for $1.3 million) had to be sold off to deal with accusations of embezzlement and fraud. Located in Pasadena, California, the home encompasses 10,000 square feet. It was described by the listing agent as “old world opulence.” But maybe that opulence is what’s pushing buyers away. It takes a certain kind of person to love solid bronze front doors and walnut paneling. A little character goes a long way and this ex-couple may have overdone it. The coffered ceilings, silk wallpaper, and sprawling gardens are just…a lot. It was originally offered for $13 million in May 2021 and reduced multiple times. In June of 2022, it sold for half that price at $7.5 million.
P. Diddy (Sean Combs) is a jack of all trades. Rapper, singer, record producer and executive, entrepreneur, and actor; unfortunately, real estate just isn’t his thing. Like many before him, Combs made the potential mistake of tailoring the apartment to his specific tastes. Skidmore, Owings & Merill designed the space. Apparently, the rapper decided he didn’t need one of the bedrooms. He had the designer team turn it into a media room instead. One of the bathrooms became a wet bar. Some have speculated that the location – the Park Imperial – just isn’t desirable anymore, as other celebrities have left the area. Combs bought the apartment for $3.82 million in 2005. It was listed for $8.5 million in 2012, but had no interest. The price dropped a handful of times before landing at $6.5 million. It finally sold for for $5.7 million – a cash offer.