The 30 Cars Expected to Sell for the Most Money at the 2016 Pebble Beach Auctions (2024)

An original works entry to the 1932 Mille Miglia, this Bugatti is claimed to be mostly original (it was restored in 2013) and to have numbers-matching components. Given the fact that new Bugattis today start at $2.5 million, spending $10 million on one of these surely seems worth it to one-up commonplace-by-comparison Veyrons and Chirons.

Photo by Mathieu Heurault / Gooding & Company

Originally fitted with a four-passenger "tourer" body, this Bentley 8-Litre was rebodied with Le Mans–style Vanden Plas bodywork in 1938. The Bentley flitted among a number of owners until it was purchased in 1968 by one of the owners of the Ferrari 500 Superfast that's also on this list of utmost expensive cars. That owner eventually sold the car 45 years later, but, you know, small world.

Photo by Darin Schnabel / RM Sotheby's

Dual overhead camshafts on an inline-eight with a gear-driven supercharger? This impressive powerplant motivated Alfa's 8C 2300, of which just 190 were built. The racing version, dubbed the Monza, paired this engine with lighter bodywork and a shortened chassis, although not all were built by Alfa Romeo. This car was, but others were produced by Scuderia Ferrari, Enzo's race team before founding his eponymous car-building enterprise. Gooding & Company's auction listing seems to boast that this car wasn't built by Ferrari—it's pretty rare that declaring a car wasn't assembled by Ferrari is a good thing.

Photo by Brian Henniker / Gooding & Company

This rare Alfa was fully restored only recently from a rolling chassis—which had been shortened in length and modified to fit a Corvette V-8 at some point early in its life in Brazil—and a Touring Spider body that had been discarded in the 1950s by a team in Argentina that may have been working with the very same Alfa 8C 2900B some years later. The potentially matching set was reunited in the late 1990s, the frame lengthened to its original dimension, and a dual-supercharged four-cylinder engine sourced and fitted. The story is almost too improbable to believe, but it's a good tale, and this is going to be an expensive car.

Photo by Darin Schnabel / RM Sotheby's

Billed as "one of the last great unrestored Ferraris" by Gooding & Company, the 166MM Berlinetta is indeed unrestored—in fact, it borders on scruffy. We think it's perfect, at least for an early racing Ferrari. Under its worn hood sits a 2.0-liter Colombo V-12 engine (for perspective, today's Mazda MX-5 Miata has a 2.0-liter inline-four—one that makes 15 more horsepower than this twelve) paired with a five-speed manual. This particular Ferrari had its original Touring body updated by Zagato in 1953 before eventually ending up on a Detroit used-car lot, where a couple traded a Triumph TR2 and some money for it. A later owner blew the engine and replaced it with a small-block Chevy V-8 (!) before selling it (with its original engine) to a college student who daily-drove it for years and later put it in storage for decades. The (former) student eventually sold the car in 2007 to a collector who rebuilt and reinstalled the original V-12. To think that, throughout the 1960s, this championship-winning Ferrari was used as a regular car—even one for a student!—and then forgotten until recently is quite cool. It also makes us wish we had a time machine to go back and snatch up all these discarded old Italian race cars, which back then were deemed of little use in a world making constant, rapid automotive progress.

Photo by Mathieu Heurault / Gooding & Company

This is one of three examples, and it was displayed at the 1954 New York auto show. It sports stunning Anglo-Italian Bertone bodywork. It's not rocket science that this Aston is expected to bring big money. This DB2/4 Spider even has relevant Pebble Beach provenance: It won a class award at the Concours d'Elegance in 2007.

Photo by Mike Maez / Gooding & Company

This car is being offered by one of the men who originally raced it more than 60 years ago, Jim Hall. The car has survived without modification or damage. Phil Hill and Carroll Shelby raced the 750 at the 12 Hours of Sebring in 1955, finishing so closely next to a Jaguar D-type that an official review ultimately declared the winner (the victory went to the Jag). The following year, it was sold to Dick and Jim Hall, who raced it for another few years before retiring it to a life of leisure.

Photo by Darin Schnabel / RM Sotheby's

This car won the 1956 24 Hours of Le Mans with Ecurie Ecosse and has had just two owners since Ecosse let it go. Per RM Sotheby's auction catalog, this is "unequivocally one of the most important and valuable Jaguars in the world."

Photo by Patrick Ernzen / RM Sotheby's

When you think of Ferrari, the automaker's bleeding-edge racing technology, exotic lightweight materials, and sophisticated design probably come to mind. In 1956, the 250GT Berlinetta Competizione "Tour de France" epitomized those essential Ferrari qualities—with a leaf-sprung solid rear axle, four-wheel drum brakes, and single overhead cams. Okay, the racing/grand-touring coupe also boasted triple Weber carburetors and a fully synchronized four-speed manual transmission, hot stuff for its time. This specific car competed at the Mille Miglia, the Tour de France, and numerous hill-climb events.

Photo by Darin Schnabel / RM Sotheby's

BMW produced only 252 507s; combine that rarity with the car's stunning looks, and it's not difficult to imagine where RM Sotheby's came up with its pre-auction estimate for this example. The somewhat zany green color seen here is not original. The car was sold in 1957 with an off-white paint job and a red interior and was at some point repainted black.

Photo by Robin Adams / RM Sotheby's

Want to know what the difference is between an original Porsche 550 Spyder and those kit cars you see far more often? Those kit cars won't be auctioned for seven-figure prices, ever. They also lack the real 550A's racing provenance. This Porsche placed fifth overall at the 1958 24 Hours of Le Mans and won its class at the Nürburgring 1000-kilometer race that same year. It was raced frequently through the early 1960s with much success.

Photo by Mathieu Heurault / Gooding & Company

It's a classic Ferrari, it's gorgeous. and it's rare—need we say more? Oh, and it's certified by Ferrari Classiche, the Italian automaker's in-house provenance rubber-stamper.

Photo by Robin Adams / RM Sotheby's

One of only nine aluminum-bodied long-wheelbase California Spiders, this 250GT comes with a reasonably successful privateer racing history. In fact, the car spent much of its early life racing before being put away in Wisconsin through the latter 1980s and being resurrected in the 1990s to as-raced specification. It's also stunning to behold.

Photo by Brian Henniker / Gooding & Company

The 250 is one of the most desirable Ferrari models of all time, and this early short-wheelbase Berlinetta Competizione iteration is a former NART team car and took seventh overall in the 1960 24 Hours of Le Mans. It retains its original engine and transmission as well as its aluminum bodywork.

Photo by Mathieu Heurault / Gooding & Company

Fully restored in 2010, this beautiful Ferrari 250GT short-wheelbase berlinetta is perhaps better than it was when new. As it should be—the restoration was overseen by Ferrari Classiche, the automaker's in-house restoration service.

Photo by Brian Henniker / Gooding & Company

Ferrari's Superfast series of the 1960s came to include only 36 cars. This is one of them. The car originally was displayed at the 1965 Chicago auto show. After quickly passing through two owners, by 1966 the car found its way into the possession of a Detroit-area doctor, where it stayed (including more than 20 years of storage) until recently. It has just 14,075 miles on the odometer.

Photo by Pawel Litwinski / RM Sotheby's

This Mark I Ford GT40 is one of 31 road-spec cars built and is for sale through RM Sotheby's. Unlike the car later on this list going under the hammer at Mecum, this GT40 has no particularly juicy history—it's simply a really nice, original GT40 set up for road driving. As a Mark I, it is very nearly identical to the racing-spec GT40s that stormed Le Mans in the latter half of the 1960s—and we'd be okay with owning it.

Photo by Patrick Ernzen / RM Sotheby's

As if classic Ford GT40s needed a popularity bump, this year's class victory for the Ford GT at Le Mans is sure to generate even greater interest in Ford's original Le Mans project. This GT40 is one of 31 Mark I road cars and is said to have originally been used for promotional purposes by Ford's marketing department back in the day.

Photo by RM Sotheby's

Yet another 275GTB/4! This one, however, is painted an incredible shade of brown and still wears its original black leather interior well. 275GTB/4s may be thick on the ground at this year's Pebble Beach auctions, but only 330 were produced over the car's three-year run between 1966 and 1968.

Photo by Mathieu Heurault / Gooding & Company

This 27,000-mile 1968 330GTS graced the December 1969 cover of Road & Track and boasts William F. Harrah (of casino fame) as its original owner.

Photo by Brian Henniker / Gooding & Company