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Our Favorite Mercedes-Benz Headed to Auction in Monterey

Some of Mercedes’ finest meet on the auction block during Car Week

Mercedes is always an auctioneer's favorite, and this year's cluster of Monterey auctions is no different. Here are our favorite Mercedes-Benz' crossing the auction block during Car Week.

300 SL Roadsters and Gullwing Coupes

The vaunted Mercedes-Benz 300 SL has quite the presence in Car Week. Bidders can vie for one of six 300 SL variants up for grabs, in both Gullwing and roadster form. Considered an auction staple, these consistently pull seven figures, regardless of history or options

In terms of special options, racing provenance, or celebrity ownership, none of these six SLs are particularly noteworthy. Regardless, these cars would make fantastic additions to any collection. Our favorites are the candy apple-red 1954 Mercedes-Benz 300 SL Gullwing coupe sporting period-correct Rudge knock-off wheels and the handsome 1961 300 SL Roadster draped in aptly-named Fantasy Yellow paint.

1971 280 SE Coupe and Convertible

From an outsider's perspective, you would have a difficult time explaining why these cars are so valuable to collectors and enthusiasts. Visually, they are handsome cars, but their large dimensions and soft character eliminate any pretensions of performance.

The secret to the impressive market value of the Mercedes W108 is the incredible craftsmanship, quality, attention to detail, and timeless slab-sided bodylines. W108s are best viewed as the first S-Class Coupe; large two-door variants of the full-sized W108 four-door. Production numbers were low, leading to tall price tags and demand that can never seem to catch up.

Gooding & Co. offers a coupe and an ultra-desirable cabriolet. Both cars are from 1971; powering each is the fantastic 200-hp, 3.5-liter M116 V-8 engine. The coupe wears a special midnight blue roof and wheel covers in contrast to the stark white body, blending well with the blue-and-tan interior.

The Cabriolet was purchased new by 'Ol Blue Eyes himself as a birthday present for his 23 year-old daughter. Tina Sinatra enjoyed the car for 15 years before selling it to her neighbor, who continued to maintain and drive the car for many years. The Cabriolet was sold to the current owner in 2002, who continued to enjoy the car until this year.

Expect the coupe to claim $250,000 - $275,000, and Sinatra's 280 SE Cabriolet to take home $275,000 - $350,000.

An Extremely Rare and Obscure 2004 CLK DTM

Before the mighty CLK63 AMG Black Series landed on our shores, Europe was busy playing with the 2004 CLK DTM AMG. Like the Black Series, the DTM is a hardcore, stripped-out, hunkered-down variant of the regular CLK AMG, putting lap-times ahead of creature comforts.

Externally, the DTM wore aggressive boxed fender flares, meant to ape the appearance of contemporary DTM race cars. A functional aero kit was added, including a front splitter, rear diffuser, and large trunk-mounted wing. Special lightweight wheels shod with super-sticky tires hide massive track-ready brakes. Inside, the cockpit is covered from roof to floor with carbon fiber, leather, aluminum, and microsuede surfaces.

Under the hood, a potent 5.4-liter supercharged V-8 engine spits out 574 hp and 590 lb-ft of torque, enough twist to slingshot this weapon to 60 mph in just 3.9 seconds, on its way to a top speed of 199 mph.

If this sounds like the perfect garage companion to your Black Series, you might want to hold-off on bidding. The CLK DTM was never officially imported to the U.S., meaning this particular example remains in the States under the Show and Display clause. As such, the new owner might not be able to register it for street use, and must be content with trailering the car to trackdays and events.

The 2004 Mercedes CLK DTM is expected to change hands for $350,000 - $425,000.

Three Pre-War 500 K Cabriolets

If you were a star or starlet from the 1930's, and wanted to uphold an extravagant appearance, you drove a Mercedes 500K Cabriolet. The swoopy, voluptuous roadster was an icon of automotive elegance and excess during the pre-war era and has become a Concours darling.

Three very different forms of the 500 K are up for grabs during Monterey. RM Sotheby's is steward to a gorgeous 1934 500 K Cabriolet A, wearing Mercedes' own Sindelfingen bodywork. This wonderful Benz was sold new to an owner in Switzerland, and eventually made its way to the streets of Cleveland, where it enjoyed  a long ownership under department store owner Walter Halle. The car was gifted to a museum in 1990, when it was sold into private ownership.

Gooding & Co. 's 1937 540 K Cabriolet C is an evolution of the 500, utilizing variants of the same powertrain, chassis, and running gear. Of course, the 540 K carried a little more power, a little more luxury, and a little more refinement over the 500, but not enough to separate the two from each other.

This 540 K is presented with the desirable "steep rear" bodywork, and is painted in the same bright red hue as the 1934 500 K. It was delivered new to a British customer, and survived the ravages of World War II before turning up in Colorado in 1975 after a 40-year gap in ownership history. After a stint in a Las Vegas collection, the 540 K traveled to Japan, where it remained until it was acquired by the current owner in the early 2000s.

Finally, Bonhams presents a 1935 500K Cabriolet A in a rich blue color, with a history stretching through a multitude of owners. The car retains its numbers-matching 5.0-liter  supercharged inline-eight engine, allowing a top speed of right around 100 mph.

All three of these Mercedes' are expected to take home $2,000,000 - $2,600,000.

An Artifact from Before Mercedes was Mercedes-Benz

This gaslight-era car is a relic from Daimler's pre-Mercedes-Benz history, a 1904 Mercedes-Simplex 28-32 HP Five Seat Rear Entrance Tonneau. This purple wooden-wheeled car has a storied history almost as long as its name.

The Mercedes-Simplex was a robust and luxurious car created by the Daimler Motoren Gesellschaft (Daimler Motor Society) corporation, a predecessor to modern Mercedes-Benz. Under the hood of this runabout is a 5.3-liter four-cylinder engine, pushing out a contemporarily-impressive 32 hp. This was routed to the rear wheels through a four-speed manual transmission, mated to a chain drive. This was enough get-go to motivate the Simplex to a top speed of 65 mph, a very high top-speed for the era.

After serving as the runabout for a wealthy lumber baron, this Mercedes-Simplex was drafted into military use, a fate found readily by powerful and reliable luxury cars of that era. Following the war, the car was sold to a French farmer, who stored it on his property until an avid collector and enthusiast purchased and restored it back to show condition.

The car enjoyed a history of shows and event participation, eventually sold to a preeminent car collection in 1999, where it has remained until recently. Now, for the first time in the past decade, a Mercedes-Simplex will cross the auction block to the tune of $2,500,000 - $3,000,000.

1952 Mercedes-Benz 220 Cabriolet A "Rose Garden"

Renowned artist Hiro Yamagata has an interesting outlook on automotive restoration. According to RM Sotheby's, the Japanese silk-screener lovingly brings Mercedes' 220 Cabriolets back from destitute condition, before covering them from bumper-to-bumper in vivid paintwork.

This particular example wears a design known as the "Rose Garden," and has remained in the private collection of known collector Vinnie Mandzak, and now carries a sale estimate of $200,000 - $250,000.