These homeowners may have started out with fabulous fortunes, but as maintenance and mortgage fees mounted, they simply couldn't keep up with their accruing debts. Take a peek behind the doors of some of the most opulent homes in America, and discover just how their owners went from millionaires—sometimes billionaires—to filing for bankruptcy, forced to relinquish the properties which had in many cases decimated their bank accounts. Click or scroll on to find out more...

Once the private residence of one of the world’s most renowned fashion designers, Casa Casuarina has a backstory as elaborate as its interiors. Also known as the ‘Versace Mansion’, the 23,000-square-foot property graces Miami’s star-studded Ocean Drive. However, in 2013 its Telecom entrepreneur owner, Peter Loftin (far right), was forced to put the landmark up for auction after his company was placed into Chapter 11 bankruptcy.

So how did Casa Casuarina find itself at the mercy of the highest bidder? Built in 1930 by architect and oil heir Alden Freeman, the incredible mansion was inspired by the Alcazar de Colon, a colonial palace in the Dominican Republic where the family of Christopher Columbus resided in the early 16th century. However, the real story doesn’t start until Gianni Versace stumbled upon the property more than 60 years later.

Following a reported $33 million (£29.4m) worth of renovations, Versace commissioned a grand new south wing, mosaic garden, and dazzling 54-foot-long swimming pool lined with 24-carat gold. Tragically in 1997, the designer was assassinated on the steps of his beloved home. At the start of the Millenium, it was bought by Loftin for $19 million (£16.9m) and in 2009, was leased by hotelier Barton G. Weiss.

In December 2011, VM South Beach (belonging to the Nakash family) filed a federal foreclosure suit, alleging Peter Loftin had defaulted on a $25 million (£22.3m) mortgage note, according to Forbes. Later, Loftin countered the suit, alleging multiple counts of fraud. A bankruptcy trustee also laid claim to the property as a minority shareholder, Scott Rothstein, had been convicted of a $1.2 billion (£1b) Ponzi scheme. 

By July 2013, a US bankruptcy court had approved the sale and it was declared as ‘the most unique property that has ever been sold at auction'. Despite its sweeping staircases, unique sculptures, and hand-painted walls, the mansion’s asking price nose-dived from $125 million (£111m) to $75 million (£67m), and the infamous property sold to VM South Beach LLC for just $41.5 million (£37m).

Dubbed ‘the largest and most expensive urban property in the world’, Nile Niami’s $500 million (£445.9m) passion project ‘The One’ was seized by the LA County Superior Court in September 2021. With more than $200 million (£98.1m) in debts, the 105,000-square-foot mansion was auctioned off for just $141 million (£125.7m)—less than half the $295 million (£263m) listing price.

Designed by renowned Los Angeles architect Paul McClean, the gargantion hilltop home is situated in the celebrity-clad neighbourhood of Bel Air. Having defaulted on $165 million (£147.1m) in loans used to finance the project, according to court filings obtained by CNBC, the producer-turned-developer’s LLC, Crestlloyd, filed for bankruptcy and the 21-bedroom, 49-bathroom complex entered receivership.

It comes as no surprise that several of The One’s claimants opposed the sale, blaming the lack of certificate of occupancy, alongside the war in Ukraine for scaring off potential bidders. However, interested parties from the Middle East and Asia were reported to have toured the excessive dwelling—likely drawn by its endless list of luxurious amenities, including a 50-seat cinema, spa, four-lane bowling alley, and even a nightclub.

Conversely, the iconic property’s largest creditor Don Hankey, holding $132 million (£117.7m) in claims, supported the lacklustre result, along with Chad Roffers, president of Concierge Auctions where Niami’s monolith was sold. On the day of the auction in March 2022, the gavel went down on the winning bid belonging to Richard Saghian, founder of apparel line Fashion Nova. 

Despite the shortfall in asking price, The One still obliterated the record for a home sold at auction in the US and the world, previously belonging to a Beverly Park mansion that was auctioned for $51 million (£45.5m) in 2021. At least there will be enough space in the 10,000-bottle wine cellar when Saghian comes to celebrate his ‘steal’ and can accommodate his party guests in the 50-car underground garage.

Designed and commissioned by plastic surgeon to the stars, Dr Alex Khadavi, this Bel Air mansion is the stuff of dreams. The palatial home boasts 21,000 square feet, including seven bedrooms, 11 bathrooms, a champagne tasting room, a home theatre, and a tequila bar. Extravagant marble finishes estimated at $7 million (£6m) and 24-karat gold dust embedded in the floors ensure this unique home is the absolute pinnacle of opulence.

The property recently sold at auction for $45.8 million (£40.8m), reports CNBC, but had been listed since May 2021 for an eye-watering $87.8 million (£78.3m). Khadavi is reportedly furious at the result. The celebrity cosmetologist’s mansion was up for auction as he has filed for bankruptcy, and the proceeds will not be enough to pay off his debts.

Grand steel entrance doors are a reference to Frank Lloyd Wright’s mirror house. A floating marble bridge leads towards a towering front door that pivots open to reveal breathtaking views. On the main floor, a retractable DJ table sits in the middle of the foyer and a glass elevator is located in a Feng Shui koi pond with a Salvador Dali clock.

The cost of construction ballooned to more than $46 million (£39m), and Khadavi even fired his architect and contractors before the build was complete. He allegedly grew agitated during the works and according to the Daily Mail, stated: "people don't take pride in what they do. Nobody wants to work these days." Despite a rocky road to completion, the grand residential home stands proud, with stunning panoramic city views—hence the name 'Palace of Views'.

The interior furnishings are the height of luxurious and futuristic living. A unique NFT gallery houses digital art, with physical pieces adorning the walls throughout the house. An opulent soaking bathtub is in the main private bathroom, which features gold fixtures, dripping with luxury.

Dubbed America’s most expensive home, this $125 million (£111.5m) mansion in Beverly Hills was once a hub for some of America’s most illustrious elite. Hosting John and Jackie Kennedy on their honeymoon back in 1953 and later being used as a set in Marlon Brando’s iconic film The Godfather, this property is really a piece of Golden Age Hollywood history.

Real estate investor Leonard Ross purchased the mansion back in the 1970s but filed for Chapter 11 bankruptcy due to a whopping $75 million (£66.9m) in unpaid debts, reported Gulf News. He tried, unsuccessfully, to sell the property in 2018 for $135 million (£114m) and later became embroiled in a legal battle with mortgage lenders.

The house takes influence from Italian and Spanish architecture, with ornate carved ceilings and wall panelling. Originally built in 1925 by architect Gordon Kaufman—a key figure in the construction of the Hoover Dam—the impressive property boasts many period features that add to its heritage charm. Externally, the house looks like an Italian villa that would fit perfectly on a Tuscan hillside.

The ‘H’-shaped main house greets guests with a huge 50-foot entrance hall and comprises 19 bedrooms, 29 bathrooms, two screening rooms, two dining rooms, reception rooms, a billiard room, and its own double-storey library. Outside, you’ll find a further dining area that accommodates 400 people, a guest house, two tennis courts, and a pool with pool house.

Expansive, manicured gardens stretch across 3.7 acres and boast a series of water features, entertaining spaces, and architectural archways—a stunning backdrop for events. In fact, Ross’ 1990s renovation of the iconic property was with the express intention to hire it out for events, with the hope that the estate would become self-sustaining. Unfortunately, this income stream didn’t materialise, but the stunning architecture speaks for itself.

Former business billionaire Sam Wyly was forced to sell his stunning Tudor-inspired Texas estate back in 2017 as one of the requirements of a civil judgement, in which Wyly was ordered to pay the Internal Revenue Service $1.1 billion (£892m) by a federal bankruptcy judge. The five-bed, five-bath mansion was placed on the market for the first time in 50 years for a court-approved $12.5 million (£11.1m).

Sam Wyly was first placed on Forbes’ list of richest Americans back in 2000, with an estimated net worth of $750 million (£685m), skyrocketing to $1 billion by 2010. However, following a series of investigations by the Securities and Exchange Commission and the Internal Revenue Service that same year, Wyly was charged with federal tax fraud to the tune of $1.3 billion (£1.2bn), one of the largest tax evasion cases in history. The loss of this Highland Park property was just one of the many consequences of Wyly’s bankruptcy settlement.

The 7,579-square-foot home was designed by celebrated architect Charles D. Hill in 1924, and features three fireplaces, hardwood floors, and highly intricate, Tudor-style woodwork throughout. Overflowing with character, the home offers all the elegance and grandeur of its 16th-century inspirations, with all the modern comforts that years of painstaking renovation and restoration have afforded.

The home features a formal dining room, living room, kitchen, sunroom, study, and game room, and is replete with charming details including crown moulding, mullioned windows, French doors, and a barrel ceiling. Set on just over an acre, the property boasts stunning views of the Dallas Country Club in Highland Park, which it overlooks.

A particular highlight of this opulent estate is the master ensuite, which looks more like a cathedral than a domestic washroom. With a vaulted ceiling, oak-panelled soaking tub, crystal chandelier, and exquisite mosaic floor, this is certainly a bathroom fit for a king.

This 50,000-square-foot, 52-room mammoth of a mansion in Farmington, Connecticut seems to carry a bankruptcy curse for any who attempts to own it. The property was originally constructed in 1985 for Colonial Realty founder Benjamin Sisti, who went to prison for bankruptcy fraud just over a decade later. Sisti sold the home to Lithuanian businessman Romas Martsinkiavitchous, who was also facing bankruptcy, and who then passed the property to former boxer, Mike Tyson.

After spending millions in renovations, Tyson attempted to offload the property less than a year later when he, too, went bankrupt, eventually selling to renowned rapper 50 Cent for $4.1 million (£3.7m) in 2003. Inevitably, 50 Cent filed for bankruptcy in 2015, and while he had attempted to shore up his floundering finances by placing the property on the market for $18.5 million (£16.5m) in 2007, it was not until 2019 that the ill-fated estate finally sold for just $2.9 million (£2.6m), an 84% price cut.

However, it’s not hard to see why the enormous estate struggled to secure a buyer, nor why it has successfully bankrupted each of its successive owners. With 21 bedrooms and 25 bathrooms, the property is one of the largest private residences in America, and cost 50 Cent $108,000 (£96.3k) a month in maintenance, including $5,000 (£4.5k) on gardening alone, court papers revealed when the rapper filed for bankruptcy.

With countless lavish special features, the property feels more akin to a hotel than a home. As well as its numerous bedrooms, the mansion includes a range of opulent additions courtesy of its two most recent owners, which include an indoor pool and hot tub, a nightclub, an indoor NBA-sized basketball court, indoor shooting range, multiple game rooms, a green-screen room, a recording studio, movie theatre, and, most unconventional of all, stripper poles.

The home sits on 17 acres, which includes a second, outdoor basketball court featuring a G-Unit logo, a helicopter pad, and an infinity pool. While the estate is currently supposedly under the ownership of Florida businessman and serial restauranteur Casey Askar, we can’t help but wonder how long he’ll be able to hold on to such a problematic property!

In 2017, actor Stephen Baldwin lost this expansive Hudson River home to foreclosure after failing to pay his mortgage for six years. With a $7,000 (£6k) monthly mortgage, Baldwin’s debt had snowballed to a jaw-dropping $1.1 million (981k) by 2016. The debt-driven house sale was also not the first period of financial difficulty for Baldwin, who was charged with failing to file his New York State tax returns for many years in 2012, according to the Daily Mail.

Baldwin initially took out a loan of $812,500 (£725k) to purchase the 3,071-square-foot home back in 2000, but within a decade had stopped paying his monthly mortgage. After the property was foreclosed by the bank, it was sold at public auction for a shocking $100 (£90), despite its estimated value of just over $1.5 million (£1.4m) at the time of sale.

With four bedrooms, four and a half bathrooms, and sweeping views of the Hudson River, the property is certainly worthy of its six-figure price tag. Originally built in 1850, the home is steeped in plenty of history, having played host to a young Jackie Kennedy, who spent her summers there when the estate was owned by her uncle, according to listing agent, Compass.

 While the home has been lovingly renovated over the years to keep it in line with modern standards, the property has nevertheless maintained much of its mid-century charm, with leadlight windows, clawfoot tubs, and wide-plank hardwood flooring. Spread across three storeys, the main floor offers large, light-flooded family spaces, with the bedrooms housed on the second storey, and the basement providing recreational space.

In spite of its age, the home’s interior is remarkably bright and airy, with high ceilings and a beach cottage-inspired colour palette. The brand-new kitchen features bright white cabinetry, granite countertops, a farmhouse sink, and stainless-steel appliances. The property is also designed to maximise the stunning views of the Hudson River, with numerous terraces, sunrooms, and covered porches, each overlooking the newly constructed Tappan Zee Bridge.

Life imitated art for this Leaving Las Vegas star when Nicholas Cage lost his sprawling 14,306 square foot Vegas mansion to foreclosure. Despite his Forbes ranking as the fifth-highest paid actor in the US last year with earnings of $40 million (£35.7m), Cage’s extravagant spending habits have led him to lose several of his homes, unable to pay off the numerous loans he has taken out against them.

Cage purchased the property in 2006 for $8.5 million (£7.6m), and attempted to sell it in 2008 for $9.95 million (£8.9m), later lowered to $9.49 million (£8.5m), but with no success. One year later, the bank foreclosed on the mansion amid revelations that Cage owed $14 million (£12.5m) in unpaid taxes, and the home was almost immediately snapped up by a buyer for just $4.95 million (£4.4m).

According to the New York Post, Cage considered buying back the property when it was placed on the market again for $6 million (£5.4m) just last year, but it never came to fruition. Why did the home still hold such a special place in his heart in spite of all the financial difficulties it posed? Well, with seven bedrooms, 11 baths, a 10-car garage, and breathtaking views of the glittering Las Vegas skyline, there is certainly lots to love about this problematic property.

The home’s open floor plan is clearly designed for entertaining A-listers, with flawlessly connected living, dining, and kitchen spaces, not to mention the commercial elevator for staff and deliveries. A state-of-the-art media room provides the perfect setting for home screenings, while downstairs, the finished basement includes a game room, kitchenette, staff quarters, and plenty of storage space.

If you’re looking for relaxation, the enormous 3000-square-foot master suite boasts its own steam room and sauna, as well as a luxurious walk-in closet. Alternatively, take a dip in the infinity pool overlooking the city below, and let your troubles drift out over that dazzling skyline.

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