30 Cars Expected to Sell for the Most Money at the 2016 Pebble Beach Auctions

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.

Vying for the distinction of most expensive car on offer at Pebble Beach if you rate cost by dollars per horsepower, this 112-year-old Mercedes-Simplex packs 32 horsepower and features brakes on only its rear axle. Despite its age, the car is said to be capable of “65-mph-plus” performance.

The LaFerrari might be the hottest Ferrari hypercar on the block these days, but the mighty Enzo is still a rare and valuable stallion. Fewer than 400 cars were built, and of those just four were said to have been painted black like this one.

Can you spot the schnoz on this Ferrari? The longer, lower nose was incorporated into the GTB in 1966 to reduce front-end lift at speed. And with a 3.3-liter Colombo V-12 engine, speed came easily to the 275GTB. As you’d expect, this is a rare Ferrari, but it’s also fairly low on our estimated-sale-value list, making it something of a bargain. Right?

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

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.

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.

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.

One of many 275GTB/4s available from a variety of auction houses this year at Pebble, this Ferrari holds the distinction of carrying the highest pre-auction value estimate. It also looks neat in its Grigio Mahmoud paint and was previously owned by Ferrari mechanic Terry Myr, who sold the car in 2015 out of “necessity.” This is a polite way of saying the 2015 sale was forced by Myr’s conviction for tax fraud. (There’s no word on whether his crime was influenced by income lost from not being able to charge himself labor and repairs on this expensive Ferrari.)

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.

Duesenbergs are timelessly cool, and this particular model features the extra-cool “disappearing top” body and is the only one to wear Bohman and Schwartz coachwork. It also happened to be owned by actress Marie Dressler. If you don’t know what or who any of these are, Google them.

Bonhams claims that the Ferrari LaFerrari it’s selling is the first model to be offered for sale publicly, further noting “no restrictions to ownership”—presumably in a nod to Ferrari’s restrictions on resales by original LaFerrari owners (at least for a time). Either way, we aren’t sure how this jibes with Mecum’s sale of another LaFerrari, but first or not, this bright-red example is expected to sell for a slightly lower price than the Mecum car. It’s a bargain! Oh, wait . . .

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.

As mentioned, Mecum Auctions this year will be offering the “holy trinity” of modern hypercars for sale at Pebble Beach; the hyped trio includes this Ferrari LaFerrari as well as a Porsche 918 Spyder and the McLaren P1 that appeared earlier on this list. The LaFerrari is bathed in a sinister Nero DS Opaco matte-black paint finish (one of three LaFerraris so painted) and has just 211 original miles. We think it’d be far more fun to, you know, drive this LaFerrari rather than pay ridiculous sums for it just to park it in a hermetically sealed bag all the time, but we also can’t put our money where our mouths are because we don’t have $4 million.

The first GT40 road car delivered to North America, this Mark I Ford supercar briefly served as a test and validation car for the automaker in Dearborn, Michigan, before being pressed into service as a PR vehicle. As such, the GT40 is lavishly equipped; despite being essentially a racing car, it came with air conditioning, luggage boxes, a leather interior, and chassis undercoating. Mecum doesn’t specify whether the family that came to own the car (and keep it for more than 40 years) was upcharged at the dealer for the rustproofing but does note that the sealant did its job, keeping the car fresh and clean for its recent restoration.

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.

In the market for a race car driven by Rolf Stommelen, Paul Newman (yes, that Paul Newman), Brian Redman, and Bobby Rahal? This iconic, Hawaiian Tropic–liveried Porsche 935 is it, and the car won a few races you might have heard of in its day. It placed second overall (and first in its class) in the 1979 24 Hours of Le Mans and won the 1981 Daytona 24 Hours and 1983 Sebring 12 Hours outright. The car was raced extensively through 1987, continuing to perform well nearly a decade past new.

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.