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40 Most Expensive Classic Cars Of Today’s High-Priced Auto World

Vukasin HerbezApril 12, 2022

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34. 1957 Buick Roadmaster

The forgotten piece of Americana is this ’57 Roadmaster. At the top of Buick’s model line, Roadmasters were cars that combined elegance with prestige and powerful engines. This example, priced at a cool $185,000, is the most desirable model because it is convertible and powered by a 364 V8 engine producing 300 HP (via Classic Cars).

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Even by today’s standards, 300 HP is not insignificant. But for late 50’s standards, it was insanely powerful. This example was the object of no-cost restoration and is perfect as a result.

1967 Ford Mustang GT fastback
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33. 1967 Ford Mustang

Mustang got its first redesign in 1967 when Ford introduced a slightly bigger and more luxurious model. The design was better and more elegant and the options list was longer than ever. Performance lovers finally got a big-block option with the 390 FE V8 engine producing 325 hp. However, if you think this was a crazy-fast Mustang that burned rubber, you’re mistaken (via MediaFord).

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This was indeed a fast car, but it was more of a Grand Tourer than a muscle car because of its specs. The engine was taken from the Thunderbird and was more suited for cruising than drag racing. With the bigger dimensions of the 1967-68 Mustang and better equipment, this was the perfect engine for making a compact luxury coupe. If you want this legendary pony car, be prepared to pay over $70,000 as a result.

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32. 1964 Jaguar E-Type

Introduced in 1961, Jaguar E-Type was a sensation on both sides of the Atlantic. Despite Jaguar’s long-lasting tradition of fine sports cars, the E-Type was years ahead of its time. The car had a superb design, four-wheel disk brakes, independent rear suspension, and powerful straight-six engines. It was derived from the Le Mans-winning C and D Type racers. And it was as fast as any Ferrari or Maserati at the time as a result (via Hagerty).

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But the best thing was the price. The E Type had the looks, power, and performance of high-priced Italian exotics but cost just a fraction of the price. However, today drivers will need to pay over $70,000 for a decent example because of its rich tradition.

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31. 1957 Ferrari 335 S

With a price of “about $36 million,” the 1957 Ferrari 335 S is one of the most expensive cars ever sold. This astronomical figure probably has you asking, is this car worth such a fortune? It probably is because it’s one of the most legendary Ferrari race cars from the 1950s. The 335 S was a very successful racer based on iconic 250 series models.

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It is powered by a 4.0-liter V12 engine with almost 400 HP and a top speed of around 190 mph, making it the fastest car in the world when released in 1957 because of this performance (via Ferrari).

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30. 1939 Alfa Romeo 8C 2900B Spider

With a sales price of just under $20 million, this incredible Alfa Romeo was one of the most expensive pre-war cars ever sold. What makes it so valuable? A lot of things. First, it was based on Le Mans-winning chassis with a smooth, straight-eight engine, which provided this gorgeous roadster with convincing performance.

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Second, its unique body was designed by Carrosseria Touring from Milan, one of the finest coach-building companies ever. Third, its rarity was a significant factor. Only 32 such cars were ever constructed, only 12 had convertible bodies, and only 7 had roadster bodies on an extended chassis. This is one of those seven incredibly sought-after machines that fetched an unreal price because of their rarity (via Classic Car Auctions).

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29. 1962 Ferrari 250 GTO

Probably the most legendary, sought-after, and valuable classic Ferrari is the 250 GTO. The car was introduced in 1962 as the high-performance/racing version of the 250 series. The car was a separate model due to numerous changes to the engine and chassis. The 3.0-liter V12 delivered around 300 HP and the car was a winner on race tracks worldwide as a result of its power.

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Only 36 cars were ever made in two distinctive series. The 250 GTO, although it was road legal, was practically a race car for the street. It cost over $20,000 new. But today if you want one, you might need to be a billionaire since the asking prices are over $45 million as a result of its rich history (via Ferrari). In fact, one even sold for a record $48.4 million in 2018, making this car a record-setting model because of its value (via Forbes).

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28. 1935 Duesenberg SSJ

Despite being on the market for only 24 years, from 1913 to 1937, Duesenberg left an everlasting mark on the global car industry thanks to this vehicle. This brand was so fantastic that even today, 80 years since it was gone, people still recognize the name and the legacy. Affectionately called “Duesy,” Duesenberg was responsible for some of the greatest American-made cars.

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The idea behind the brand was to offer luxury cars with powerful engines and uncompromising performance. Duesenberg had the performance, and the hearts of most models were fantastic straight-eight engines that were hand-built and very fast for the day. The SSJ models had supercharged engines with 320 HP. This was an insane number in 1930 as a result. That’s why this model sold for $22 million recently (via Supercars).

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27. 1964 Aston Martin DP215

Car fanatics know Astons are very expensive. After all, James Bond’s favorite car cannot be cheap because of the prestige required. However, we never knew that a racing prototype from 1963 could achieve an astronomical $21.4 million price tag at auction in 2018. This race car was built to compete in the 1963 Le Mans and did so with celebrity drivers behind the wheel.

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However, it didn’t win. It managed to go almost 200 mph on the legendary Mulsanne straight. Carefully restored and wholly original, this is a precious piece of racing history because of its speed (via RM Sotheby’s).

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26. 1994 McLaren F1 LM

There’s much written about the F1. Car writers have discussed how it was designed and how it changed the supercar world forever. The F1 was introduced in 1992 and stayed in production until 1998. McLaren produced 106 cars during that period including the GT-R versions, which were highly successful racing models (via Motor Authority).

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The F1 featured a bespoke 6.1-liter V12 engine made by BMW Motorsport, which delivered 627 HP and had a six-speed manual transmission. The example pictured is the ultra-rare LM semi-competition version, of which only five were built. Hence its insane price of $19.8 million as a result.

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25. 1937 Bugatti T57 S Atalante

As one of the finest pre-war brands, Bugatti is always fetching high prices at auctions. But the 57S Atalante is a true collector’s dream. It’s a gorgeous coupe powered by a straight-eight engine with a beautiful coupe body.

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This one sold for over $8.5 million and it could fetch a bit more if sold again. The wealthy customers held Bugatti’s exclusivity, performance, and unique engineering aspect in high regard, hence the extreme prices (via Supercars).

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24. 1985 Porsche 959 Paris Dakar

The Porsche 959 is one of the fastest and most technologically-advanced supercars of the 1980s. The 959 was a super Porsche in every way; not just in design but also in performance and price. The 959 had a 3.0-liter turbocharged flat-six engine with 450 HP that was transferred to all four wheels over an intelligent AWD system, the first of its kind (via RM Sotheby’s).

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The car was also equipped with traction control, ABS, and a host of electronic systems, which helped the driver as a result. Since it was so advanced, it was highly successful for off-road racing due to these improvements. The Dakar-winning example sold for almost $6 million.

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23. 1964 Ford GT40 Prototype

The story of the Ford GT 40 is a saga of enormous effort, incredible support, luck, and several talented people all gathered at one place in one moment in time to create history. The GT 40 became an outright legend and a symbol of an American race car dominating the European racing scene (Via Robbreport).

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It won four Le Mans races in a row and defeated Ferrari on its turf. Logically, such vehicles will have hefty prices, and recently, the 1964 prototype sold for an impressive $7 million.

8 Most Expensive Vintage Cars Only Ultra Rich Can Afford - Marketing Mind
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22. 1931 Bugatti Royale Kellner

Ettore Bugatti only made 6 Royale models with enormous 13.9-liter engines. Each sold at an astronomical price when the car was released in the early ’30s. Despite the name, no king ever owned one and all six proved to be a tough sell due to its price.

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Today, the Kellner version (Kellner was a coach-builder) is one of the most iconic Bugattis because of its rarity. It was sold for almost $10 million in the early ’90s. If an example went on sale today, it would most likely fetch at least double that figure as a result of its status as one of the rarest, most expensive classic cars on the market (via CarBuzz).

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21. 1954 Mercedes W196 Silver Arrow

The post-WWII Mercedes Benz renaissance started not on the streets but on the race tracks. The weapon of choice was a silver W196 F1 car with legendary driver Juan Manuel Fangio behind the wheel (via New Atlas).

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The vehicle was unbeatable because of its many qualities. It showed that Mercedes is a design powerhouse with much to deliver. Of course, such an iconic machine can’t be cheap due to its lofty status in the car industry. It sold for an astonishing $31 million.

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20. 1934 Bugatti T59 Sports

Bugatti built his name on the world’s race tracks before conquering the luxury market. That’s why racing models are always a bit more sought-after than sedans or coupes.

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This particular one has a stellar racing history, original condition, and some documented light restoration. Knowing all of that, the selling price of over $13 million shouldn’t be surprising as a result (via Sports Car Market).

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19. 1931 Duesenberg Model SJ

This car is another Duesenberg from a similar period but with different mechanicals and a more formal body. The SJ Convertible Coupe was an elegant roadster, one of just three made (via Supercars).

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However, what makes this one so special and expensive is that this is the only one equipped with a supercharger straight from the factory. Also, the first owner was William Lyons, the man behind Jaguar. It sold for a cool $4.5 million because of its rarity and speed.

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18. 1962 Ferrari 330 Testa Rossa

Even though Ferrari produced numerous racing cars from the very beginning, the Testa Rossa is one of the most popular and significant. Based on 250 architecture but with dozens of improvements, this was one of the most successful race cars of the period (via Rick Carey).

1962 Ferrari 330 TRI/LM - Images, Specifications and Information
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The 330-series engine provided more power than its predecessors, which meant more speed and competition success as a result. This particular example sold for $6.5 million and was known to participate in the 1962 24 Hours of Le Mans race.

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17. 1964 Ferrari 250 LM

Despite the name and the 3.0-liter engine, the 250 LM could not be considered a genuine part of the 250 Series because of two important details. First, it was introduced at the end of the production. Second, it was a mid-engined model with racing aspirations (via Bloomberg).

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However, it never successfully raced. Only 35 were ever produced. But regardless of that, it managed to achieve a ludacris $67 million at the auction due to its highly-desired history and speed.

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16. 1934 Mercedes 540K Roadster

The 540K was the ultimate pre-war Mercedes luxury convertible. Powered by a supercharged straight-eight engine, it was extremely expensive. Only a dozen or so were built.

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Not many have been preserved because of the overall rarity. The ones that were sold for astonishing prices due to the car’s history. The last one fetched almost $12 million on auction a few years back (via Sports Car Market).

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15. 1962 Shelby Cobra 260

The Shelby Cobra is one of the most iconic American sports cars. Based on the AC Bristol but powered by Ford’s V8 engines, the 260 V8 version is one of the early examples with significant history.

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The later models got a more powerful 289 V8, but those early 260 V8 models are very sought after by collectors because of several reasons. Each original Shelby Cobra is very expensive, but this one sold for a whopping $13.7 million. This was due to the fact that it was actually Carroll Shelby’s car (via Classic Car Auctions).

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14. 1964 Ferrari 275 GTB Speciale

The successor to the 250 GT was the 1965 Ferrari 275 GTB. It had a slightly bigger V12 engine, more performance, and better technology due to recent advancements. However, it retained a classic design with a long front end and short rear. It sold as a coupe and a convertible with a GTC nameplate (via Motor Trend).

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This example was “C,” and was known for its unique features as a semi-racing car. They were enough to set the sale price at almost $26.5 million as a result.

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13. 1957 Ferrari 250 Testarossa

One of the first extremely successful Ferrari race cars was the gorgeous 1957 Testarossa. The car had a 250-series V12 engine of over 300 HP that was unbeatable in the late ’50s as a result.

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The success of racing models helped Enzo Ferrari sell more streetcars and establish Ferrari due to that success. Of course, every Testarossa is extremely valuable. But this one sold for almost $40 million (via Auto Blog).

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12. 1931 Bugatti Royale Berline de Voyage

As you probably know, only six Bugatti Royales were made and one of them was Brline de Voyage. This model featured a closed body and plenty of space. It was envisioned as a luxury sedan for traveling, hence the name. However, it was too expensive and only one such car was ever constructed because of its price tag.

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This is that vehicle. It managed to fetch almost $14 million at auction due to its rarity and remarkable history (via Journal Classic Cars).

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11. 1956 Ferrari 290 MM

With an auction price of $22 million, the 1956 Ferrari 290 MM is one of the most expensive cars ever sold. Even though this model isn’t a household name in Ferrari racing history, it is still significant due to the list of drivers who drove this car (via Top Car Auctions).

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Practically anybody who was a celebrity driver in the 50s was behind the wheel, making this red Barchetta a true example of a well-preserved racing machine.

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10. 1961 Aston Martin DB4 Zagato

As a world-renowned sports car brand, Aston wanted into racing in the early 1960s, briefly becoming the owner of “the world’s fastest production car” title. Their weapon was the Aston Martin DB4 Zagato, a lightweight 300 HP version of the DB4 Grand Tourer (via Motor Trend).

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Aston’s engineers tried hard to achieve this power output with three carburetors and two spark plugs per cylinder. The original example sold for over $13 million.

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9. 1953 Jaguar C-Type

During the 1950s, Jaguar was heavily involved in racing, especially at Le Mans. First, there was a C-Type racing car, but soon, the company developed a brand new and much-improved D-Type that proved to be an equally successful and influential racing car (via Robb Report).

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The C-Type was the car that launched Jaguar as a performance brand and managed to win the legendary 24 Hours of Le Mans race. Very few were built since it was a purpose-made race car, and surviving examples are known to fetch high prices. This one achieved over $13 million.

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8. 1956 Ferrari 250 GT Berlinetta

Based on the 250 Europa, the GT was Ferrari’s main model up to 1964. It was also the definition of the 250 Series and one of the first Ferraris produced in significant numbers, which brought some financial security to the factory (via Supercars).

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Numerous versions were available, and this one was called Tour de France since it was victorious in the race held under the same name. It was a bit more potent than stock and featured several race-spec modifications. The price? $13.2 million.

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7. 1970 Porsche 917 K

In 1971, Steve McQueen made an ultimate racing movie with “Le Mans.” The film featured real racing and real racing cars, especially the legendary Porsche 917. However, even before the movie was released, the Porsche 917 was a legend in racing circles.

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The 917 incorporated everything that Porsche as a company had in its arsenal. It had a unique body of lightweight materials, a flat-12 engine made out of two flat-six units, exceptional aerodynamics, and a top speed of over 200 mph. Today, it has a price of over $18 million (via IMSA).

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6. 1979 Pontiac Trans Am

Unfortunately, the days of big cube engines and high horsepower ratings were gone in 1979, so Pontiac decided to invest in new technology to generate power. That new technology was turbocharging, and in late 1979 it introduced the Trans Am Turbo (via Hagerty).

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The engine in question was a 301 V8 with a Garrett turbocharger bolted onto it. The power output was relatively modest at 200 to 210 HP, but the torque was high at 340 lb.-ft, which resulted in a hint of performance. Highly-preserved examples can fetch over $50,000 at auctions.

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5. 1984 Jeep Grand Wagoneer

The Grand Wagoneer is the ultimate vintage luxury off-road vehicle. The fact that it was produced from 1963 to 1991 with just a few tweaks is proof of its qualities. The Wagoneer was powered by numerous inline-six and V8 engines. It had both rear-wheel and all-wheel drive.

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The most coveted models came from the 1984 to 1991 Chrysler era, when the car went through a series of upgrades. With air conditioning, high-quality audio, power seats, and optional woodwork, the Wagoneer was a well-equipped car. The cleanest examples can fetch $100,000 at auction (via Carscoops).

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4. 1991 Jaguar XJS

When it was introduced in 1975, Jaguar XJS had the daunting task of eclipsing the aging-yet-still-gorgeous E-Type. Although it wasn’t as beautiful as the car it replaced, this ugly duckling was still a sales success, with production lasting up until 1996 (via Hemmings).

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On the classic car market, though, the XJS is in E-Type’s shadow. But that means one thing – you can find a V12-powered example for quite a reasonable sum. One of the best examples you can find is this convertible with low mileage and a price of just over $28,000.

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3. 1962 Plymouth Valiant Custom

One of the best and most interesting classic American compact cars was the legendary Plymouth Valiant. With flamboyant styling, smaller dimensions and engines, and a low price, Chrysler deliberately presented the car in Europe, hoping to sell many cars there.

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The Valiant was styled after many of Chrysler’s concept cars from the late ’50s and looked much more expensive and upscale than the rest of the compact car market. This one is a renewed custom car valued around $100,000 (via Classi Cars).

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2. 1969 Plymouth Barracuda Convertible

Introduced just two weeks before the Ford Mustang, Barracuda was the first pony car in history. During most of the 1960s, it was in the shadow of the Mustang and Camaro yet in 1969, it debuted with upgraded styling and more options.

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The 1969 model was available in three body styles, and here we have a cool-looking convertible equipped with period-correct wheels and a desirable color combination. The price is relatively affordable at almost $40,000 (via Classic Cars).

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1. 1957 GM Futurliner

One of the craziest but still roadworthy concept cars was the famous GM Futurliner bus. Designed in 1939 as a part of the Parade of Progress, Futurliners were custom-made buses that used a regular GM Truck Division drivetrain.

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Redesigned for the ’50s, Futurliners gained a recognizable shape and each one of them was designed to show specific technology or achievement. The interior featured an information desk. GM produced 12 of these vehicles and only nine of them survived. One of them sold recently for a staggering $4.4 million (via Barett-Jackson).

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