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World’s Most Expensive Classic Cars
1937 Bugatti Type 57S – $4.4 million

When relatives of the recently deceased and “eccentric” Dr. Harold Carr opened the garage he’d left to them in his will, they had no idea what to expect. Sure they’d heard that there might be a Bugatti in there, but that was just a bit of local legend. As it happened, there really was a Bugatti in there—and, when it went to auction at Bonham’s Retromobile car show in February of 2009, it sold for €3,417,500—around $4.4 million at the time.

This 1937 Bugatti Type 57S Atalante was originally purchased by Earl Howe a month after it left the Bugatti works. Over the 8 years that he owned the car, Howe added new bumpers, a luggage rack and rearview mirrors. It was later brought up to SC specification with the addition of a Marshall K200 supercharger by its next owner, J P Tingay. Eventually, the car found its way into the hands of Lord Ridley, who held it for a year before selling it to Dr. Carr. Combine this pedigree with the fact that only seventeen Type 57S’s—a version of the Type 57 modified specifically for competitions—were produced and you have quite an expensive car.
1961 Ferrari 250 GT California Spyder – $10.8 million

Sold in May 2008 at the RM Auctions/Sotheby’s Ferrari Legend and Passion auction, this Ferrari 250 GT was owned by former Magnificent Seven star James Coburn for twenty-five years. During that time, Coburn would test his skills against fellow enthusiasts Steve McQueen and James Garner. In fact, one of the latest lines of Ferraris, also designed by Pininfarina, has been named “California” in honor of Coburn’s car.
1957 Ferrari 250 Testa Rossa – $12.4 million


One of only twenty-two of its kind, chassis no. 0714TR features a distinctive pontoon-like design by Carrozzeria Scaglietti. The Ferrari 250 TR is famous for having won ten of the nineteen races in which they were driven between 1958 and 1961.
This particular TR won 4th place when driven by Piero Drogo in the 1000 km Buenos Aires in January of 1958. Drogo drove it one more time, in the Grand Prix of Cuba, before he sold it to American Alan Connell who drove it in nine races and spent most of that time in 1st or 2nd place in class. It featured in twelve more races between 1960 and 1963, making it one of the most raced Ferraris of all time.
It was sold at auction in Maranello, home of Carrozzeria Scaglietti and birthplace of the TR, for an impressive sum of €9,020,000.
1934 “Star of India” Rolls-Royce Phantom II Continental – $13 million

Hans-Gunther Zach, owner of the Rolls-Royce museum in Germany, is selling off his entire collection–including the museum’s premiere acquisition, the Star of India.
This bespoke Rolls was one of 281 Continental Phantom II’s ever produced. Built for the Maharajah of Rajkot, one of its custom features is, among its 14 headlights, a pair that turns with the steering wheel. Also particular to the Star of India is its unique orange-over-aluminum color combination.
The Star of India was auctioned alongside twenty-four other rare Rolls-Royces and another three Bentleys. After the auction, it appeared for sale at $13 million, but the listing was later removed.
Peter D. Williamson Bugatti Type 57S Atlantic – $30-$40 million

If you thought the Bugatti Type 57S above was expensive, then check out this piece of phenomenal piece of Bugatti history. The Bugatti Type 57SC Atlantic was based on the “Aérolithe” concept car. The Aérolithe’s Electron and Duralumin construction required external riveting, resulting in a distinctive seam not unlike a dorsal fin. Despite the Atlantic’s aluminum construction, which required no such riveting, the seam was retained.
Only four Type 57SC Atlantics were produced and only two have survived to this day. Fashion guru Ralph Lauren owns one while the other was owned by late Bugatti collector Dr. Peter Williamson. The Williamson Bugatti, chassis #57374, was the first Atlantic off the production line and was originally owned by Lord Philippe de Rothschild of London. While it was drastically modified by its second owner, Dr. Williamson restored it to its original specifications after acquiring it for $59,000 in 1971. After Williamson’s passing, it was sold to an undisclosed buyer, reportedly for a sum between $30 and $40 million.