The streets might not be paved in gold, but the world's most expensive residential roads are brimming with prestige properties boasting some of the most eye-watering price tags we've ever seen.
Of course, it's not all glitz and glamour. Hiding behind these prestigious postcodes are stories of scandal, tragedy and intrigue.
Click or scroll on to stroll down the planet's most expensive thoroughfares and see for yourself...
London is the world's fourth-most expensive city according to the World Economic Forum, so it's no surprise that real estate here can come with a staggering price tag.
While the most expensive street in the capital is a hotly contested title that's frequently changing, Phillimore Gardens (pictured), is usually among the cream of the crop. Tucked away in the Royal Borough of Kensington and Chelsea, the leafy residential road boasts an average house price of £23.8 million ($30.3m), according to data from Halifax. Quite some feat given the national average is £288,000 ($366k).
Phillimore Gardens and its surrounding streets were built by William Phillimore in the 1770s and many of the grand houses are still owned and rented out by the Phillimore Estate today.
Thanks to its enviable position running alongside Holland Park, notable residents have long flocked to the street. After American shipbroker Ernest Simpson (pictured here in October 1936) divorced his wife, Wallis Simpson, he lived just around the corner on Upper Phillimore Gardens in a home "stuffed" with servants, according to The Times. Wallis infamously went on to marry King Edward VIII, sparking the abdication crisis.
Former British Prime Minister David Cameron also called Phillimore Gardens home, residing in the exclusive enclave as a young boy before his family moved to Berkshire.
Notable musical names including rock star Freddy Mercury lived in the area too, and former Rolling Stones guitarist Bill Wyman opened his restaurant Sticky Fingers on the corner of Phillimore Gardens in May 1989. Wyman is pictured at the opening with his then-girlfriend Mandy Smith. The eatery eventually closed due to the pandemic in 2021.
In 2019, Phillimore Gardens hit the headlines when the owner of a £2.5 million ($3.2m) flat in this end-of-terrace building rented out her luxury home with disastrous consequences. Elizabeth Stirling let out her immaculate five-bedroom apartment via Airbnb to a woman who claimed she wanted to host a small surprise baby shower and dinner party. However, her property was overrun with hundreds of revellers. The party was eventually shut down after a late-night court order was obtained by police, according to an interview Stirling gave to The Daily Mail.
While the home's resin floor was scratched and rugs were burned – reportedly amounting to thousands of pounds worth of damage – Stirling's art collection, which included original works by Andy Warhol, Jasper Johns, Joan Miro and Picasso, survived the ordeal.
The occasional police incident certainly hasn't hurt house prices. In the last six years, three homes on the road have sold for £37 million ($47m) and above, one of which was a two-bedroom semi-detached home.
If you'd like to live among London's elite on the capital's priciest street, some extravagant homes have been up for grabs in the area over the past year. This five-bedroom, five-bathroom townhouse was on the market in late 2023 for £24 million ($31m).
The home has been beautifully restored and claimed the title of London's Best Single Residence at the UK Property Awards in 2018, according to the listing. Key features in the state-of-the-art home include bathrooms clad in Italian marble, two original fireplaces and a bespoke Boffi kitchen with an additional chef's kitchen with its own walk-in fridge.
One of the priciest places to live in the whole of the US is Indian Creek Island Road in Florida. The expensive street is the only one on the island, stretching almost the whole way around the exclusive enclave. Known as 'billionaire bunker' island, the upscale community consists of just 32 lavish mansions, a highly-selective golf club and around seven vacant plots.
Thanks to its tight security, privacy and high-profile neighbours, homes on the island have gone for an average of around £31.4 million ($40m) since March 2021. That's a staggering figure when compared with the national average of £320,000 ($408k).
Let's take a look around and meet some of the street's most well-known residents...
Totally manmade, the pristine island hideaway was dredged from Biscayne Bay in the early 1900s. During the late 1920s, it was developed into an exclusive country club with an 18-hole championship golf course at its heart. It fast became a winter retreat for tycoons of industry – and has been ever since.
Indian Creek Island has long had a staid, conservative atmosphere and is considered the classier, understated alternative to Miami's other billionaire enclave, Star Island.
These days, the island's seclusion and top-notch security are a major draw for the moneyed inhabitants. A veritable fortress, Indian Creek has its very own police force that scrupulously vets visitors. The community is only accessible by bridge via a heavily guarded gatepost, while armed officers patrol the island on land and by boat 24 hours a day, seven days a week.
While you don't have to be a billionaire to live on 'bunker' island, it certainly helps. In fact, the most recent resident to move to the secretive community is none other than the third-richest man in the world Jeff Bezos, and his fiancée Lauren Sanchez. The couple reportedly picked up this home (centre) in October 2023, for a record-breaking £62 million ($79m). The mansion features seven bedrooms and 14 bathrooms. But it wasn't their only purchase on the island.
Just four months earlier, Bezos snapped up the £53 million ($68m) house next door (far left). The three-bedroom, three-bathroom home was built in 1965. Rumour has it that Jeff and Lauren may raze one or both properties to make way for an enormous mega-estate.
Bezos will be one of many billionaires living on the exclusive road. His new high-net-worth neighbours include hedgefund tycoon and former Sears CEO Edward Lampert, art collector and former Philadelphia Eagles proprietor Norman Braman and Hotels.com co-founder Bob Diener.
Among the celebrities who call Indian Creek Island Road home are NFL quarterback Tom Brady and Spanish crooner Julio Iglesias. Ivanka Trump and Jared Kushner and their three children also have two properties on the isle.
Back in 2020, Ivanka and Jared parted with £25.3 million ($32.2m) to snap up a coveted empty lot. Then in April 2021, the pair also picked up a £18.9 million ($24m) fixer-upper mansion nearby.
After a two-year renovation, the luxurious home was finally habitable and Ivanka celebrated her 42nd birthday there (pictured) on 30 October 2023.
You might be wondering why this rather unassuming street features in a gallery filled with incredible locations. Well, that's because this is Hallstrom Close, which was ranked the most expensive residential street in Australia in 2023. The distinctly ordinary-looking road sits on Hallstrom Point, a rocky promontory that juts into Long Bay, a prime position in Northbridge, an upmarket suburb on Sydney's Lower North Shore.
Let's find out why people pay a premium to live on such an unassuming street...
Hallstrom Close is named after Sir Edward Hallstrom (pictured here with George the gorilla in 1967), one of Australia's most well-known philanthropists and businessmen, and a past resident of the area.
After enduring a childhood of hardship and poverty, Hallstrom rose to become a millionaire fridge magnet, having invented and patented the highly successful 'Silent Knight' refrigerator range. He was also passionate about animal conservation and poured much of his money into Toronga Zoo, which is still open today.
Knighted in 1952, Hallstrom's last home, Figtree House, and its grounds, which contained a private zoo, stretched along the shore of Figtree Point, which is now Hallstrom Point – where Hallstrom Close lies.
The house was demolished in 1971, a year after his death, and was subdivided into eight housing plots. Many of the fig trees, which gave his house its name, still stand on the grassy point and have become a public reserve.
Homes on the close typically cover 3,455 square feet and have five bedrooms – and an impressive median value of £3.9 million (AUD$7.5m/$5m), according to The Property Tribune and January 2023 data from Suburbtrends. That's just over 10 times the current national average of almost £399,000 (AUD$758k/$507k), as recorded in December 2023.
This incredible house sold in 2011 for £3.2 million (AUD$6m/$4.7m).
Despite the fact Hallstrom Close was named after an eccentric inventor, it's fair to say the nine homes that stand on the road look a little conventional from the street.
But appearances are deceiving. This five-bedroom, four-bathroom home on the road sold in April 2021 for a staggering £4.7 million (AUD$8.9m/$5.9m), and is currently valued at around £5.2 million (AUD$9.9m/$6.6m).
So what is it that makes these homes so desirable?
The incredible view is why everyone is clamouring for one of Hallstrom Close's homes, although they rarely come onto the open market. Each waterfront mansion enjoys outlooks over the calm waters of Long Bay, taking in Bay Point and several waterfront reserves to the south.
The homes are built in levels that descend the rocky shoreline, making them much larger than they appear from the street. Each has its own jetty and deep-water dock and most have a swimming pool to boot.
Northbridge Golf and Cricket Clubs are just a few streets away, while the famous Sydney Opera House is a quick 15-minute drive south.
While there's nothing for sale on Hallstrom Close itself, take a few steps around the corner onto Coolawin Road and you'll find this incredible modern mansion, which is currently on the market.
Described in the listing as a "waterfront masterpiece," this newly built, architectural gem has stunning bay views and is accessed via a concrete bridge, which crosses over a "serene" central garden. The five-bedroom, six-bathroom home features fireplaces, bespoke cabinetry, a gym, a luxury steam room, a fully-tiled pool and a jetty for your boat.
While the price is only available on application, the suburb median is £3 million (AUD$5.8m /$3.9m), so be prepared to pay a premium!
It's easy to see why Vancouver's 'golden mile' is one of the priciest places to live in Canada. Otherwise known as Point Grey Road, the upscale street skirts the waterfront to the west of the city, overlooking English Bay.
The road stretches along a long oceanfront portion of Kitsilano, one of Vancouver's most coveted neighbourhoods. Known for its beautiful beach, public saltwater pool, seawall walking trail and 17 parks, Kitsilano attracts young professionals, tourists and high-profile Canadians alike. Point Grey Road continues west into the next neighbourhood, Point Grey, which has three beaches, a yacht club, a tennis club and an abundance of luxury properties.
According to a January 2024 report by real estate listing site Zolo, the average house price in Kitsilano is £822,000 (CA$1.4m/$1m), while prices in Point Grey come in at around £2.3 million (CA$4m/$3m). Let's take a look around...
Stars such as Ryan Reynolds and Joshua Jackson have lived in Kitsilano, but Point Grey Road's most high-profile house is known as the Chip Wilson mansion, named after its owner, the founder of athleisure brand Lululemon.
Built in 2008, the seven-bedroom, nine-bathroom mega-mansion (pictured) has over 15,000 square feet of living space and sits on a 0.7-acre plot. It also boasts a pool, a hot tub and a tennis court.
With an estimated net worth of £5.3 billion (CA$9.1bn/$6.8bn), the businessman certainly has plenty of money to splash on the £39 million (CA$74m/$55m) property.
Wilson isn't the only high-profile Canadian with links to this moneyed street. Before he became Canada's prime minister, Justin Trudeau was a French and maths teacher at West Point Grey Academy (pictured), a private school just around the corner from the westernmost end of Point Grey Road. Trudeau taught at the school for almost three years.
The future leader called Vancouver home for a time while he was studying for his Bachelor of Education degree at the University of British Columbia. He then spent his early teaching career learning the ropes in classrooms across Vancouver.
A diverse array of properties line Point Grey Road. Landmark homes on this wealthy stretch include this magnificent manse, built back in 1912. A historical gem of yesteryear in a region being slowly repopulated by flashy new-builds, it became Metro Vancouver's most expensive sale in more than three years when it sold for £15.9 million (CA$27m/$20.2m) in 2020.
It drew plenty of media attention during its time on the market, most notably because British tabloids speculated that Prince Harry and Meghan Markle were considering snapping up the estate. Alas, it was a rumour that ultimately came to nothing.
If modern masterpieces are more your thing, you could snap up this masterpiece-in-the-making on Point Grey Road for £9.3 million (CA$15.8m/$11.8m). Plans and permits are already in place to build the impressive four-bedroom, six-bathroom home, which will cover 4,400 square feet and offer sea views from each of its three floors.
Current plans include a rooftop deck with a hot tub, a 28-foot pool and a four-car garage with a car elevator and turntable, but – as it hasn't actually been built yet – the buyer can still make changes to suit their own tastes.
The new owner won't just gain 180-degree views of the North Shore Mountains and English Bay, they'll also be buying up a slice of life on one of the most exclusive streets in Canada.
Think of Germany's most expensive street and a sophisticated boulevard in Berlin, Munich or Hamburg may spring to mind. However, the country's priciest thoroughfare is Hobokenweg, located in the village of Kampen on the picturesque island of Sylt.
Renowned for its charming thatched cottages, sea views and peaceful position, property prices on Hobokenweg reportedly range between £3,200 (€3.7k/$4k) and £4,000 (€4.6k/$5k) per square foot as of May 2021, according to a local realtor. In comparison, the average price of a house in Germany in 2022 was around £223 (€260/$284) per square foot.
Homes on the extraordinary street are typically 3,200 to 5,400 square feet – something not typically found elsewhere on the island – and they rarely come onto the market. When they do, their scarcity means they regularly fetch double-digit millions. The most expensive thatched roof villa in the area reportedly cost over £25.8 million (€30m/$32.8m) and is said to be owned by a German IT entrepreneur.
So why does the road command such staggering prices? Well, it's largely down to the popularity of the area. Kampen has existed since around 1543 but it didn't become a tourist destination until the 1920s. Drawn to the charming cottages, rolling dunes and white sand beaches, artists and writers – including Nobel laureate Thomas Man – flocked to the village.
It was around this time that a local statue was declared, requiring all houses in Kampen to be traditionally built from brick with a thatched roof. The statue is still in effect today – even the bus stops in Kampen are thatched!
After the Second World War, tycoons made rich by West Germany's rapid regeneration holidayed in Kampen. Everyone from actors to playboys and politicians were drawn to the newly moneyed village, including Gunter Sachs, the famed art collector, photographer and third husband of Brigitte Bardot.
To this day, Kampen – and the wider island of Sylt – is the premier weekend getaway destination for the country's elite and it's easy to see why.
High-profile parties and society weddings are regular occurrences, while the Beach Polo World Cup is held yearly on Sylt's white sands and the Windsurf World Cup takes place in the island's azure waters.
So wealthy are the residents and holidaymakers of Kampen that the local vending machine supplies freshly baked bread, Dolce & Gabbana perfume, upmarket dog treats and luxury drinks.
10 minutes from Kampen lies one of the island's most popular locales – the famous beach of Westerland. A huge draw for tourists and residents alike, it's pictured here with its iconic hooded wicker beach chairs, called Strandkorb, which literally translates to beach basket.
Overflowing with natural beauty spots, it's easy to see why the rich and famous still gravitate to Sylt. American actor Kevin Costner is said to own a holiday house on the island, while German tennis player Boris Becker reportedly used to vacation on Sylt's sunny shores.
Given its famous visitors, it's no surprise that property on Sylt sells for millions of euros.
While homes on the highly desirable Hobokenweg rarely come onto the market, this delightful semi-detached cottage is currently for sale nearby for £5.8 million (€6.8m/$7.5m). The three-storey home has four bedrooms and three bathrooms and is built in the traditional Kampen style, in red brick with a neatly thatched roof, frieze gable, stable windows and wooden lattice windows.
Set away from the hustle and bustle of the city, Nassim Road is unarguably the most exclusive – and most expensive – road in Singapore. Once a sprawling nutmeg plantation, it's now a mix of embassies, up-market condo buildings and the most sought-after residential building of all: the Good Class Bungalow, or GCB, as they're known.
To understand the allure of Nassim Road, you first have to understand the Good Class Bungalow. An icon and a status symbol, a home can only be classed as a GCB if it has at least 15,000 square feet of land, while the building itself can't be more than two storeys high.
If that wasn't hard enough to come by in one of the world's most populous cities, a GCB can only be located in certain neighbourhoods of certain districts, and the home itself can't take up more than 35% of the plot.
Perched atop a hill on Nassim Road is Eden Hall, the official residence of the British High Commissioner to the Republic of Singapore and one of the most recognisable homes in the area. Known as 'The Wedding Cake' or 'Wedgwood House' due to the pale grey exterior walls covered with delicate white plasterwork, Eden Hall was built in 1904 for an Iraqi-Jewish businessman whose wealth was built on rice and opium.
When Singapore fell to Japan during the Second World War, the owner and his stepson were imprisoned and Eden Hall became home to a Japanese admiral. After liberation, British Forces took up residence before it was finally sold to the British Government in 1955 for just £56,000, which would be about £1.2 million ($1.5m) today.
To put that sum into perspective in modern terms, the British sold off half the land at Eden Hall in 2001 and one of those lots was resold in 2012 for £37.4 million ($47.8m), according to The New York Times. Such is the staggering value of Nassim Road real estate.
In 2019 the most expensive single home ever to sell on Nassim Road changed hands for £136 million (S$230m/$172m). The buyer is rumoured to have been Facebook co-founder Eduardo Saverin, though this has never been officially confirmed. The massive plot came with a pool and tennis court and covered 84,543 square feet of land, which is big enough to encompass five whole bungalows.
That same year, British inventor James Dyson bought a GCB just around the corner for £26.5 million (S$45m/$34m). The modern home, which includes an indoor waterfall and a cantilevered spiral stairway, was the vacuum mogul's second in the country. Earlier in the year, he bought Singapore's largest and most expensive apartment, a three-story super penthouse, which he snapped up for £43.5 million (S$73.8m/$55.5m).
More recently in 2023, a number of high-value homes on Nassim Road changed hands too. According to MSNews, three mansions – highly desirable GCB properties – were bought up for a total sum of £122 million (S$206.7m/$155m) by an Indonesian family.
The two-storey homes are said to have been extensively renovated in 2015. Each property reportedly offers five bedrooms and a swimming pool.
GCBs are typically only available to Singaporean citizens to purchase, however, exceptions are reportedly made for super-rich buyers who make a significant investment in Singapore's economy.
GCBs on Nassim Road come on the market extremely rarely, which only elevates their value. However, condos on the street are more readily available. The 14 units in Les Maisons Nassim (pictured) are currently under construction, but many have already sold.
This duplex penthouse with five ensuite bedrooms is currently available for £46 million (S$78m/$58.6m). It's set to become the most expensive apartment in Singapore should its incredible levels of luxury and "unmistakable status symbol address" attract the full asking price.
The Cape Town suburb of Clifton has long been South Africa's most expensive neighbourhood. Curling around a peaceful bay on the southern Atlantic seaboard, Clifton attracts the South African elite thanks to its white sand beaches, easy commute into Cape Town and exclusive residential streets. Historically, Nettleton Road is the priciest of them all.
Perched high up in the hills above the bay, Nettleton Road offers homeowners incredible views of the mountains to the south, as well as the pristine beaches and glittering sea below.
Homes on the exclusive street and nearby Clifton Road range from £3.3 million (R80m/$4.3m) to £12.6 million (R300m/$16m). Let's see what all the fuss is about...
You can spy Nettleton Road here, home to the distinctive glass-fronted black house at the top of the photo (more on that in a moment). As you can see, it has the most enviable position, rising above the hotels and apartment blocks below.
“It’s the most sought-after road on the African continent,” said Annette Hepburn, a Pam Golding estate agent in Clifton who spoke with Independent Online – and that was back in 2016 when Nettleton Road first topped the list of South Africa's most expensive streets. Asking prices have only gone up since.
Homes in this playground of the rich and famous are often super modern with "daring architecture, magnificent views and imposing façades," according to Paul Turner of Engel and Volkers Cape Town.
As of May 2023, Cape Town is reportedly home to 7,200 millionaires, 26 centi-millionaires and one billionaire, many of them no doubt settling in Clifton.
Just down the coast from Clifton, Llandudno is another highly desirable Cape Town location for the super-rich, with residences there commanding an average price tag of £1 million (R25m/$1.3m), according to 2023 data from real estate aggregate property24.
Home to one of the area's most scenic beaches, the enclave attracts wealthy nature lovers and those looking for a quieter pace of life.
Yet Llandudno can't eclipse the staggering house prices found throughout Clifton, which has seen figures soar some 800% since 2000.
If you have £7.2 million (R170m/$9.1m) to spare, you could live in one of Nettleton Road's most iconic buildings – recognise that black mirrored house from earlier?
An architectural landmark of the street, the cliff-hanging home enjoys a front-row seat to the best views of the Atlantic Ocean and the Twelve Apostles mountain range.
The minimalist, state-of-the-art home features floor-to-ceiling sliding doors, which open fully to reveal a terrace and a vertiginous, fully-heated infinity pool.
According to the listing, the five-bed, seven-bath home is completely off-grid, supported by a diesel generator, solar panels with backup batteries and a gas backup for additional heating – especially valuable given the enforced power cuts caused by South Africa's electricity crisis.
This magnificent home truly is the pièce de résistance of the country's most exclusive road.
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