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The 15 most expensive cars sold at Monterey Car Week

From barely-driven Bugattis to race-winning Ferraris to achingly beautiful Alfa Romeos

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A black Ferrari convertible parked by the sea
Image: RM Sothebys (Fair Use)

The events that make up Monterey Car Week, feature some of the most expensive, rare, and gorgeous cars known to man. Many of them appear at auction, where they’re offered to the highest bidder. Some Monterey auction cars sold for under $10,000, but the cheapest car on this list sold for $3.36 million.

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Many of the cars on this list have backstories that are too long to include on a slide, so if you want to learn more about each lot click the title of each slide and it will take you to the auction website to learn more. I am generally more a fan of cars that are owned by millions, rather than cars that cost millions, but that doesn’t mean I don’t appreciate most of the cars on this list.

From barely-driven Bugattis to race-winning Ferraris to achingly beautiful Alfa Romeos, this list is full of gorgeous, rare, and unfathomably special cars. Special doesn’t even begin to describe many of these cars; some are truly irreplaceable. These are the most expensive auction lots that sold during Monterey Car Week.

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This is one of 20 Sport Noire Chirons ever produced worldwide, and its odometer only reads 418 miles.

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This is the second of 10 twin-cam Ferrari 275 GTBs specced with alloy coachwork. It’s the winner of multiple awards, and has a well-documented provenance by a Ferrari historian.

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This is one of 80 Chiron Super Sports with 1,,578 horsepower and a 273-mph top speed. It shows just 243 miles on the odometer which is sad, but it looks pristine.

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This convertible Doozy has a 420 cubic-inch inline-8 cylinder engine that produces 265 horsepower and has a three-speed manual transmission. It’s one of three Disappearing-Top cars fitted with dual rear spare tires, and retains its original engine, chassis, and firewall. It’s among the most desirable of all Duesenbergs.

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The Alfa Romeo 2.3 is a legendary car that was used in racing , and obviously has a gorgeous coachbuilt design. Though this example was never fully restored, it was well-kept and is the winner of numerous concours awards. It was sold with its original logbook and a fascinating history file.

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This is the first Porsche 935 ever built, with chassis number 935-001. It was a factory prototype used for testing and development, and had an illustrious racing career. It has been fully restored to concours standards, and is the sole Works Martini Racing Porsche 935 in private ownership.

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Listen to that glorious sound : Ferrari 333SP onboard

This is one of nine 333 Evoluziones built by Dallara, and has several podium finishes and wins under its belt, including Pikes Peak, Sebring, and Halifax. It also raced in the 1997 24 Hours of Le Mans, and was raced by Alboreto, Montermini, Moretti, Papis, Theys, and Vélez.

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1958 12 Hours of Sebring

This is the last of 17 three-louver Tour de Frances built, and was delivered new to American racing driver George Reed. It has an admirable racing history, and has a well-documented provenance. It’s presented as it was originally sold with a matching-numbers engine.

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This is the most successful of all racing 275 GTB/4s, and was the only car to achieve a class victory in a major international race. It won its class at the 1969 24 Hours of Daytona, and it still has its original, matching-numbers engine and gearbox.

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This is the last of four 857 Sports ever built, and has multiple podium finishes in 1956, including with Carroll Shelby and Jack McAfee. It’s been restored, and has a matching-numbers 276-hp four-cylinder engine.

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This F50 is the 47th of 349 ever built, and one of 55 original US-delivery F50s. It has 8,556 miles in the odometer, and is in outstanding condition. It was the platinum winner at Cavallino Classic Palm Beach last year, and is Ferrari Classiche certified and has its original books.

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A black Ferrari convertible parked by the sea
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This car was used in the 1967 Italian film Le Dolci Signore, and is the 19th of 50 long-wheelbase cars ever built. It has a matching-numbers engine, and retains its factory color combination of Nero over Rosso.

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This is a one-off car that was the prototype for the 410 Sport Scuderia Ferrari Works cars. Carroll Shelby drove it to victory at the 1956 Palm Springs Road Races, and retains the original numbers-matching engine.

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This gorgeous Spider is one of five long-chassis 8C 2900B Touring Spiders known to exist. It has a twin-supercharged inline-8 engine with 180 horsepower, and a 4-speed manual transmission. This was the first time it has ever been publicly auctioned.

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This little convertible was the most expensive lot sold during Monterey Car Week. It’s the first-ever Ferrari 250 GT SWB California Spider and was showcased at the 1960 Geneva Motor Show. It’s widely regarded as the finest and most important 250 GT SWB California Spider available. It has never publicly been available for sale prior to this auction, and has its original delivery colors. It has the factory-equipped competition-spec engine, covered headlights, and removable hardtop.

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A version of this article originally appeared on Jalopnik.

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