Donald Trump has invested in countless properties over his lifetime, spanning everything from one-bedroom condos and local casinos to the dizzying heights of Trump Tower and his Mar-a-Lago HQ. But bearing the Trump name isn’t always a ticket to success, and some properties have haemorrhaged cash along the way.

Now, after the Trump Organization was found liable for massive fraud after allegedly overvaluing swathes of its properties, Donald Trump could lose some of his most iconic buildings, including his beloved New York City tower. Click or scroll through to discover Trump’s biggest real estate wins – and his most devastating losses, plus the properties teetering on the brink...

It’s no secret that Donald Trump has made his fortune through real estate. His passion for property – and the cash it generates – was passed down to him by his father Fred Trump (pictured here, right). According to a New York Times investigation in 2018, the former president inherited the equivalent of at least $413 million (£340m) from his father ⁠– a huge portion of which was real estate assets. Let's take a look through some of Trump's most notable deals...

The acquisition of the Commodore Hotel in New York was one of Donald Trump’s early wins in the world of real estate. Trump bought the rundown business in partnership with the Hyatt Organization in 1976, for $10 million, which would be about $54 million (£44.5m) today, and took on the hotel’s $1.5 million (£1.2m) of debt in the process.

It was a risky investment but over the following years, the property mogul transformed the 34-storey building into one of the Big Apple’s most iconic accommodations: the Grand Hyatt Hotel, which was rebranded in 2021 as Hyatt Grand Central New York.

By 1996, business was booming and Trump sold his half of the hotel to Hyatt for $142 million (£117m). Trump’s first major property success may not be standing for much longer though, as there are plans to permanently close the hotel after 2023. Developers intend to tear down the building and replace it with a 2 million-square-foot skyscraper, which will house retail and office space, as well as a smaller hotel.

Before he became the 45th president of the United States, and even before his 14-series stint as host of The Apprentice, Donald Trump’s name was already synonymous with big money and lavish property. Trump bought this mansion in Greenwich, Connecticut in 1982 for his then-wife, the late Ivana Trump, for a reported $4 million, the equivalent of $12.7 million (£10.5m) today. 

The rolling six-acre estate offered sweeping views of Long Island Sound and the interiors were remodelled to suit Trump’s signature excessive style. Here, Trump is pictured posing next to the mansion’s grand double staircase in 1987.

Donald and Ivana's million-dollar marriage didn’t last however, and Ivana got the couple’s home as part of the divorce settlement. She went on to sell the property for $15 million in 1998, which would be a cool $28 million (£23m) today.

Surprisingly, the buyers have been trying to offload the home since 2009, when they listed it for an eye-watering $50 million (£41m). Since then, it has been on and off the market several times, according to Zillow. Despite an interior update and a hefty price slash – it was last put on the market for $29.9 million (£24.6m) in August 2022 – it still hasn't found a buyer and the listing was pulled once again in July 2023.

Perhaps Donald Trump’s best-known addition to the soaring Manhattan skyline, Trump Tower was the epitome of eighties excess when its 58 storeys opened in 1983 – but could it prove to be his downfall?

Funded by $130 million in loans, which equates to around $401 million (£329m) today, the opulent high-rise featured fine dining eateries, high-end retailers and luxury residences.Trump initially claimed to have sold 85% of the residential units before the building opened, stating at the time that: “The apartments will bring in $268 million, all profit." 

However, a Forbes exposé published in February 2023 cast doubt on these figures, and as such, leaves the true success of Trump Tower as something of an enigma. According to the Forbes report, only 60% of the apartments had been sold by 1983, and the tower had allegedly made $45 million (£38m) by the end of its first year, significantly less than the figure Trump previously touted.

Of course, Trump Tower has had its successes over the years. When Gucci moved into the building in 2006, the deal reportedly brought in more than $15 million (£12.4m) a year on average in rent. The property was used also as a hub for Trump's 2020 election campaign, bolstering the tower's income by $1.6 million (£1.3m).

However, Forbes reported that according to historic interviews, Trump has anecdotally exaggerated the tower's finances, predicting an annual profit of around $80 million (£66m) in a 2015 interview with the publication. According to records, Trump Tower reportedly made more like $15 million (£12.4m) in net income that year.

While Donald Trump and the Trump Organization have denied any wrongdoing, Trump Tower's seemingly erratic valuations landed the former president in hot water with New York Attorney General Letitia James.

On 21 September 2022, James filed a civil lawsuit against Trump, his organisation and family members, alleging that he "falsely inflated his net worth by billions of dollars" to benefit from tax benefits and favourable loan conditions.

Trump's private penthouse in the building, where he is pictured here with the late Japanese Prime Minister Abe Shinzo, is named in the complaint, which claims: "Mr. Trump’s own triplex apartment in Trump Tower was valued as being 30,000 square feet when it was 10,996 square feet." The alleged inflation puts the penthouse's value at $327 million (£270m) in 2015, which the New York Attorney General's office declared "absurd" when the most expensive apartment sale in the building was just $16.5 million (£13.6m). 

On 25 September, Judge Arthur Engoron found Trump and his sons Eric and Donald Jr liable for fraud in the case brought by Letitia James. The trial to determine damages and other potential punishments began in New York on 2 October.

Central to the investigation was the tower's overall value. According to the claims, different valuation formulas were used to calculate Trump Tower's worth throughout the years. A different methodology was used in 2015, which saw the building valued at $881 million (£735m), $170 million (£140m) more than the year before and bizarrely, nearly $250 million (£206m) more than the recorded value the following year.

Considering the wildly inconsistent valuations and financial representations, it's difficult to tell if Trump Tower has been a great money-maker for the former president. But with Judge Engoron stripping the Trump Organization of its New York business certification, it may prove Trump's biggest loser yet. The future of the tower – and of Trump's entire empire – hangs in the balance. 

In 1984, Donald Trump opened the Trump Plaza Casino and Hotel, which would become the pièce de rèsistance of his sprawling Atlantic City empire in New Jersey. Building and decorating costs for the 32-storey Plaza added up to around $210 million, or $622 million (£512) in today's money – most of which was funded through loans.

The real trouble began when Trump started pouring money into new ventures such as the Trump Taj Mahal, instead of existing casinos like the Plaza, and just one year later, his mountain of debt had ballooned to an eye-watering $3 billion, the equivalent of some $8.6 billion (£7bn) these days.

Following multiple bankruptcy filings, Trump Plaza eventually closed its doors in 2014. Despite attempting to have his name removed from the casinos, Trump doesn’t seem to view his business interests in Atlantic City as a failure. In a 2016 interview with The New York Times, he said the city had given him “growth” and boasted that "the money [he] took out of there was incredible". The casino was demolished in February 2021. It goes to show that success is a matter of perspective...

Trump Marina Hotel Casino in Atlantic City paints a very similar picture. After welcoming throngs of gamblers in the 1980s under the name of Trump’s Castle, and then later rebranding as Trump Marina Hotel Casino, the business started to flail as much-needed funds went elsewhere. Along with the Trump Plaza and Taj Mahal casinos, Trump Marina landed their owner in multiple bankruptcy courts. 

Trump Marina Hotel Casino was eventually sold for just $38 million (£31m) in 2011, which was around a tenth of the selling price initially advertised in 2008. The waterfront site in New Jersey is now a Golden Nugget hotel and casino.

Donald Trump bought his famed Mar-a-Lago resort in Palm Beach, Florida in 1985. After his initial offer of $15 million, $43 million (£35m) in today's money, was rejected by the then-owners, Trump decided to play hardball and – in one of his craftiest real estate moves – purchased the land between the estate and the ocean for $2 million (£1.6m). He then announced plans to erect a building that would block Mar-a-Lago’s enviable sea view, knowing the move would put off other potential buyers. The tactic worked, and Trump paid just $8 million for the estate and all its contents, the equivalent of $23 million (£19m) now. 

Mar-a-Lago was transformed into a private club, charging new members a $100,000 (£82k) initiation fee. The venture brought in $15.6 million (£12.8m) in profits in 2014 alone. The joining fee was doubled to $200,000 (£164k) when Trump became president in 2017. Incredibly, not even the COVID-19 pandemic or controversies around the Trump presidency could turn this business success sour: Mar-a-Lago brought in $22.9 million (£18.9m) in revenue in 2020. 

While the club appears to continue to turn a healthy profit, it's been consumed by scandal in recent years and a legal battle that could even see Trump serving prison time...

Not only was the former president indicted in June 2023 over his alleged mishandling of government documents taken from the White House to Mar-a-Lago, but the estate was also named in Letitia James' fraud lawsuit, along with Trump Tower.

James claims that the club was falsely valued from 2011 to 2021 based on the premise that the estate's land could be developed and sold for residential use, despite Trump signing away his development rights. Consequently, its peak valuation during that period of a staggering $739 million (£609m), should have been more like $75 million (£61m), says the lawsuit.

As we know, Trump was found liable for fraud by overvaluing Mar-a-Lago and other properties, but the classified documents trial is yet to begin. Despite the controversy surrounding the property's financial statements, evidence still points to Mar-a-Lago as a successful investment and business venture – for now.

In 1995, Donald Trump brokered a deal to take over the ground lease of 40 Wall Street in Manhattan's sought-after financial district, and he described the transaction as one of his “favourite deals” in his 2008 book Never Give Up.

There have been competing reports about exactly how much Trump bought the ground lease for – at the time, The New York Times claimed the figure was just less than $8 million, or $16 million (£13m) today. According to Forbes, documents filed with the Securities and Exchange Commission show that its net operating income in 2019 was an exceedingly healthy $18.1 million (£14.9m).

Trump has leased the building for a term of up to 200 years and according to Bloomberg, it's his most valuable tower. 

Profits felt the impact of the pandemic, however, and the building's revenue in 2020 fell by more than 11% from the previous year as tenants looked to vacate the building's offices and retail premises.

40 Wall Street is also mentioned in the New York Attorney General's fraud lawsuit. According to the filing, an appraisal from 2012 put the property's worth at $220 million (£181m), yet the Trump Organization listed its value in 2012 as $527 million (£434m). In 2015, that figure grew to an even more eye-watering $530 million (£436m) according to the company. Contrastingly, The Real Deal reported that the building's valuation slumped to a significantly lower $130 million (£107m) in 2021. 

In total, Trump spent some $200 million (£164m) on renovation works, according to the Trump Organization website, and the skyscraper has been heavily mortgaged. 

In a blow for the former president, Bloomberg reported in February 2023 that 40 Wall Street had been placed on a lender watchlist due to its falling income. The property is said to have a remaining mortgage of $126.5 million (£104m) with Wells Fargo and drops in the building's commercial performance have raised alarm bells. Loans placed under lender watch indicate an increasing risk to the lender and are consequently subjected to increased monitoring and scrutiny. 

Occupancy is one of the reasons why the building has been placed under the microscope. The third quarter of 2022 saw the vacancy rate at the tower increase by almost 18%, according to official filings. Demand for high-rise office leases in Manhattan has shrunk since the pandemic, with more companies embracing remote working or hybrid arrangements. 

Moreover, expenditure has reportedly grown by 11% since 2015's exorbitant valuation of $540 million (£445m). It may be too soon to call if 40 Wall Street is heading for disaster, but things certainly don't look promising for Trump's trophy skyscraper.

Next on Donald Trump’s list of acquisitions is this majestic property in Westchester, which Trump bought in 1996 for a reported $7.5 million, or $14.7 million (£12m) in today's money. The Seven Springs estate brought a golf club-shaped twinkle to the property mogul’s eye, and he planned to convert the 212-acre estate into another Trump-branded course for the rich and famous, but protests from local residents put a stop to his plans. 

Trump then reportedly tried to build luxury homes on the site, but the project was held up by litigation and never materialised. Consequently, the estate was kept as a vacation retreat for his family.

With beautifully manicured lawns and decadent interiors, this luxurious slice of real estate consists of two homes, a number of outbuildings and rolling land.

Despite the property's lack of development, it's another of Trump's properties that has been plagued by legal woes. Seven Springs is currently the subject of a criminal probe by the Manhattan District Attorney, as well as being one of the 20 Trump properties named in the civil fraud lawsuit by New York Attorney General Letitia James. 

Back in 2002, Trump National Golf Club decided to add another plush retreat to its roster. This dazzling estate in Bedminster lies 40 miles west of New York City in New Jersey and came with a $35 million (£29m) price tag. Two years later, the property was transformed into a luxury club and golf course befitting the Trump brand. Bedminster’s 36-hole golf course was designed by renowned architects Tom Fazio and Tom Fazio II and it is accompanied by a 16-acre practice facility, an indoor golf centre and even equestrian facilities.

Membership for this illustrious hangout is estimated to cost around $350,000 (£289k), and those who have forked out for membership are then allowed to rent one of three luxury cottages or 11 suites during their stay. 

Donald Trump carries out plenty of his business dealings at his New Jersey estate, so the property hasn’t been without its controversies. Records released in July 2021 suggest the club’s finances saw a tremendous boost during Trump’s term in office, as the Secret Service spent $10,199.52 (£8.4k) of taxpayers’ money on 18 nights at the resort.

The club proved the third-biggest earner of all Trump's golf courses between January 2022 and April 2023, hauling in an impressive $46.2 million (£38m), according to Sportico. What's more, Bedminster is one of three Trump golf clubs to host the Saudi-backed LIV Golf tournaments in 2023, no doubt bringing in a pretty penny too.

Along with other Trump resorts, Bedminster is also listed in Letitia James' fraud lawsuit. It's alleged that fixed assets were used to calculate the value of the club, rather than income, a method that overlooks depreciation. Nevertheless, while Trump's dealings at the estate may have raised more than a few eyebrows, it's still thought to be a solid money-maker.

Donald Trump has strong ties to Scotland, with his mother having emigrated from the country to the United States in 1930. The real estate tycoon snapped up land in Balmedie, Aberdeenshire almost 80 years later, and converted the 1,400-acre plot into his smallest golf resort. But business was never really booming, even pre-pandemic.

Closures during the pandemic triggered losses of $1.3 million (£1.1m) for 2019, and in 2020, the Balmedie club reportedly incurred losses of $1.6 million (£1.3m). While less than in previous years, pre-tax losses came to just under $850,000 (£700k) in 2021, begging the question of where Trump is going wrong with the Scottish leisure estate. Grand plans to build a residential village close to the estate have also come to a standstill, as reported by Forbes.

The Aberdeenshire course is also named in the New York District Attorney's fraud lawsuit, which alleges that the club's valuation used "improper methods".

Dominating the Las Vegas skyline is the 64-storey Trump International Hotel, which made Donald Trump a tidy $18 million (£14.9m) during his stint in office. Opened in 2008, the hotel is owned by the Trumps and business partner Phil Ruffin. Between them, they sold more than 60 studio, one-, two- and three-bedroom apartments between 2017 and 2020. 

Sales really boomed when Trump was first sworn in, and the hotel generated almost $7 million (£5.8m) in 2017. By 2019 interest was tapering off, but condo sales still made up for around $4.4 million (£3.6m) in revenue. Between 2019 and 2020 revenue dropped from $22.9 million (£19m) to $9.2 million (£7.6m), as reported by Reuters, but this property still counts as a win for Trump – for now.

As with numerous other real estate investments in this round-up, the Trump Organization has been accused of inflating the value of the Las Vegas hotel in the civil fraud lawsuit brought in 2022.

In 2008, Donald Trump added a Greek Revival-inspired mansion to his expansive property profile, at a cost of just under $10.4 million (£8.6m). The bright white, two-storey property was built in 1981 and a row of 11 slender columns highlights its faux-historic style. Green shuttered windows span the outside walls and give a glimpse into the marble-lined foyer, which stretches into 15,000 square feet of immaculate interiors.

Trump flipped the North Rodeo Drive house in Beverly Hills just a year later for $9.5 million (£7.8m), making a loss of $850,000 (£700k). Before it was briefly owned by the Trumps, the pristine mansion had belonged to Omar Bongo, the former President of Gabon, for decades. 10 years after selling his Beverly Hills pad, Donald Trump had upgraded to another building known for its imitation Greek architecture – the White House.

Donald Trump heralded Trump Tower Tampa (pictured in the painting here) as a property that would “redefine both Tampa’s skyline and the market’s expectations of luxury” when construction work was announced in 2005. Set to be a 52-storey riverside apartment block, locals were quick to put down deposits on the yet-to-be-built residences bearing the Trump name. Yet, over the next couple of years, it transpired that it was only Trump’s name ⁠– and not his money or business acumen ⁠– that was linked to the project. 

Developers had agreed to pay the host of The Apprentice a $2 million (£1.6m) licensing fee, which later increased to $4 million (£3.3m), to use his brand to bolster interest, but that wasn’t enough to prevent the project from falling foul of the real estate crash of the mid-noughties. The Tampa developers eventually declared bankruptcy with only $3,500 (£2.9k) in assets and the plot (pictured) was later bought up by another Florida real estate developer. Trump may not have lost millions, but the project left local buyers out of pocket and dented the TV star’s reputation. 

Built to the tune of $73 million (£60m) between 2005 and 2009, Trump International Tower Chicago was set to be the tallest building in the world, but plans were altered following the attacks on 11 September 2001. That said, the building isn’t exactly a wallflower at 98 storeys, and the 5-star addition to the Trump Tower line-up was named Travel+Leisure’s best large city hotel in North America in 2010.

Two years later, a cash buyer snapped up the 89th-floor penthouse for a cool $17 million (£14m). The story of the last couple of years isn’t quite as rosy, however. The hotel’s revenue dropped from $26.2 million (£21.7m) in 2019 to $14.3 million (£11.8m) in 2020, likely as a result of the pandemic.

In 2021, the tower's property taxes were cut by $300,000 (£247k) after assessors slashed the value of the building's office space, since 95% of the square footage was reportedly vacant. 

The Doral Hotel and Country Club – one of South Florida’s most famous golf clubs – was taken on by the Trump Organization in 2012. The 700-room resort came at a price of $150 million (£124m), and Trump quickly announced multimillion-dollar plans to renovate the hotel and its golfing facilities. He also rebranded the 50-year-old resort as Trump National Doral Miami. While business at the club initially boomed, over the years, things took a turn for the worse, before making a shocking comeback in 2022.

In 2015, the resort generated $92.1 million (£76m) in revenue and $13.8 million (£11.4m) in operating income according to Forbes, but as Trump ascended up the political ranks, profits at the golf club started to slide. By 2017, revenue had slipped to $75.4 million (£62m) and operating income was at $4.3 million (£3.5m). Although 2018 and 2019 saw a slight uptick, revenues were a long way off the dizzying heights of the 2015 numbers. 

The situation only worsened when the pandemic hit America. The resort closed its doors at the beginning of the outbreak and hundreds of employees were made redundant. Revenues then tumbled to $44 million (£36m) in 2020, which was a 40% drop compared to the previous year.

However, post-pandemic, Doral became the jewel in the crown of Trump's golf empire and raked in a staggering $159.3 million (£131m) between January 2022 and 14 April 2023, according to Sportico. Although that figure takes into account the hotel earnings as well as the income generated from the golf course, it overshadows the income from Trump's second-most lucrative golfing asset – Trump Turnberry, Scotland – by over $100 million (£82.4m). 

Trump announced expansion plans for the property in January 2022. 2,300 luxury homes will be added to the site, while more commercial and retail spaces are also in the pipeline. The new additions follow a staggering $250 million (£206m) renovation of the Doral undertaken in 2016, which was unveiled by Ivanka Trump. 

That might sound rosy, but Trump reportedly financed part of the golf resort with a $106 million (£87.3m) loan from Deutsche Bank. When added to mortgage costs, that brings his total debt to $125 million (£102m). Doral, and the loan, are – you guessed it – currently under investigation as part of the New York District Attorney's fraud lawsuit against Donald Trump and the Trump Organization. While the club is definitely a money-maker for now, let's see where it stands after Trump's legal battle with Letitia James...

​​In 2014, Donald Trump confirmed he had purchased the Turnberry Golf Resort in Scotland. Trump paid $45 million (£37.5m) for the entire South Ayrshire complex, including its hotel. The business mogul himself then reportedly invested a further $139 million (£115m) in the estate. Taking on the esteemed golf course was no hole-in-one though, as Turnberry lost $21.3 million (£17.6m) in 2016. Deutsche Bank also refused Trump a loan for the resort that same year, according to the New York Times. 

The resort was closed for most of 2020 due to the pandemic, causing sales to plummet, and expenses remained high, racking up around $4.2 million (£3.4m) in operating losses. The Trump Organization secured a total of $4 million (£3.3m) in Covid-related grants from the British government, yet still reported losses of $5.3 million (£4.4m) in 2021 across its two Scottish golf clubs.

However, like Doral, Turnberry thrived post-pandemic and was Trump's second-highest earning course from January 2022 to 14 April 2023. The course and hotel combined generated an impressive $52 million (£43m). Talk about a comeback! As with Trump's other Scottish golf club, the valuation of Turnberry is similarly under the microscope after it was named in the Letitia James' fraud lawsuit. 

Another initially loss-making golf course belonging to Donald Trump is Trump International Golf Links & Hotel in Co Clare in Southern Ireland. Trump spent around $20 million (£16.6m) on the estate in 2014, as reported by Forbes, and invested a further $13 million (£10.7m) in redecorating the property and revamping the golf course.

Between 2014 and 2019, Trump lost $14 million (£11.7m) on the golf course and hotel, thanks to soaring operating costs. The pandemic could not have come at a worse time for the property, and despite receiving $600,000 (£502k) of government grants, Trump lost an incredible $4.4 million (£3.7m) in 2020 alone. Between 2014 and 2022, Trump lost a total of $18 million (£15m) on Doonbeg.

However, after international travel bounced back, so too did Doonbeg's ability to make a buck and it raked in $21.8 million (£18m) between January 2022 and April 2023. The club certainly seems to have turned its luck around!

Donald Trump's penthouse in his Trump Park Avenue building in Manhattan has been on and off the market since 2007. In the past, the building has been the home of Trump's eldest daughter Ivanka and her husband Jared Kushner. Ivanka has lived in a number of Trump Organization-owned properties, including this two-bedroom, two-bathroom apartment several floors down from the penthouse suite, which she took on as a 'modest' starter home back in 2004. 

In 2017, Trump finally found a buyer for the penthouse, though the sale was regarded as controversial, as the buyer, Angela Chen, was rumoured to have ties to Chinese military intelligence.

The deal was a solid sale for the Trumps though, as Chen paid just under $15.9 million (£13.1m) for the luxury penthouse. The final price is even more staggering when compared to the virtually identical penthouse just one floor down, which sold for almost $2 million (£1.6m) less in 2016.

The apartment was one of 18 salubrious Park Avenue residences belonging to the Trump family. The Trump Park Avenue building is currently named in a fraud lawsuit brought by the New York Attorney General, after valuations of the property ranged from $90.9 million (£75m) to $350 million (£288m) between 2011 and 2021. 

Why have one gorgeous beach-front home in the Sunshine State when you can have two? This stunning seaside residence was reportedly bought by a company owned by the Trump family for just short of $18.3 million (£15m) in 2018. Neighbouring Mar-a-Lago, the property on Ocean Boulevard had belonged to Donald Trump’s sister, retired judge Maryanne Trump Barry, and it’s safe to say it’s since become a reasonable family money-spinner, but the question of whether it will deliver a decent return on investment in the long term is still unanswered.

Once the sale had gone through, the pristine Palm Beach pad was listed to rent on Trump International Realty for $100,000 (£82.7k) a month. The price was quickly reduced to a more reasonable $65,000 (£54k) in 2019, likely due to a lack of tenants. The beach house went up for sale in March 2021 and was listed for $49 million (£41m). The property was then relisted for a hefty $59 million (£49m), before being removed from the market. It's now available to rent once again, now listed for an extremely optimistic $149,000 (£123k) a month. Only time will tell if this investment delivers a profit for the Trump Organization. 

Donald Trump acquired a 4% interest in the federally subsidised housing complex Spring Creek Towers in Brooklyn from his property mogul father Fred Trump. The gargantuan affordable housing blocks were sold in 2018 for $905 million (£748m), of which Donald Trump got a sizeable $33 million (£27m).

The Trump Organization snapped up a Tudor-style home in Beverly Hills for $7 million (£5.8m) in 2007. Built in 1927, the five-bedroom, six-bathroom property sits among a 29,185-square-foot estate and is surrounded by a hedged lawn. The mock period property may have been a nod to the former president’s childhood home (pictured), which was a quaint mansion in Jamaica Estates in Queens, built to replicate a Tudor design.

The Beverly Hills house was dark grey in colour, but it was given a vibrant orange makeover when the Trumps took over. In 2019, the Trump Organization sold the property in a quiet, off-market sale for $13.5 million (£11.1m). Pictured are the interiors of Trump's childhood home, which was sold off to a mystery Chinese investor in 2017.

The Trump Organization was awarded the lease to the building in 2012 by the General Services Administration, which is an arm of the US Government and he opened the hotel in 2016, while he was the Republican presidential nominee. Between 2017 and 2019, annual revenue was reportedly around $52 million (£44m) – barely enough to cover the interest on the $170 million (£140m) loan given to the business by Deutsche Bank. The pandemic only worsened the situation and profits fell below $20 million (£16.5m). 

In 2019, and amid dwindling financials and criticism of a conflict of interest – the hotel became a hub for those looking to gain favour with the then-president – Trump listed the property for around $500 million (£411m), but couldn't find a buyer.

In June 2021, it was revealed that the Trump Organization was trying to sell the hotel once again, after revenues at the property dropped by 62% in 2020. Along with the $170 million (£140m) loan, the Trumps also spent around $200 million (£164m) renovating the property, as reported by The Washington Post, so there was a significant sum to try to reclaim in the sale. 

The lease of the property was sold in 2021 to investment firm CGI Merchant, who turned the property into a Waldorf Astoria. The sale price was a staggering $375 million (£314m), which certainly makes this precarious piece of property a win.

Described as “one of the greatest mansions in the world” by Donald Trump when he bought it in 2013, Le Château des Palmiers is an elaborately adorned villa perched on 4.8 acres of Plum Bay beachfront on the French West Indies island of St Martin. Between 2014 and mid-2016, the 11-bedroom beachside abode earned Trump between $200,000 (£164k) and $2 million (£1.6m) in rental fees, but he decided to put it up for sale in the first half of 2017 for $28 million (£23m).

At around $10 million (£8.3m) more than the typical asking price for the location, it’s perhaps unsurprising that Trump’s oceanside property garnered little interest from serious buyers. Within three months, the price tag was slashed by 40% and the château was listed for $16.9 million (£14m), before it was cut once again to $15.5 million (£12.7m). It appears to have been pulled from the market for the time being, but it's still available to rent for up to $60,000 (£49k) a week in the high season.

Before Trump snapped the property up, it was listed for $19.7 million (£16.3m) by the previous owners – so if Trump paid the asking price, the investment will amount to a loss if it sells for its most recent price tag. Whether it’s the Trump name, the struggling real estate market, or a combination of the two, this Caribbean home is proving difficult to shift.

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