The 10 Most Legendary Mercedes Convertibles Ever Built

Few automobiles evoke the same sense of prestige, craftsmanship, and timeless beauty as antique Mercedes convertibles. These vintage Mercedes Benz convertibles are rolling sculptures, embodiments of automotive history, and symbols of an era when engineering and artistry went hand in hand.

Sophia Loren, the legendary Italian actress, was famously associated with a classic Mercedes-Benz SL convertible during the height of her stardom in the 1950s and ’60s. Often photographed with the car, she embodied Mediterranean glamour paired with German engineering. 

The SL’s beauty and open-top elegance perfectly matched Loren’s cinematic allure, making the pairing iconic in both automotive and Hollywood circles. Her presence helped elevate the SL’s status as a symbol of sophistication and star power. For collectors and enthusiasts, owning a classic Mercedes cabriolet is akin to possessing a piece of motoring royalty.

The 10 Coolest Mercedes Convertibles Ever Built

1. 1955 Mercedes-Benz 300 SLR

• A motorsport legend with gullwing DNA, this rare roadster is the holy grail of Mercedes convertibles.

This car was a thinly veiled race weapon disguised as a road-going masterpiece. Built to dominate endurance racing, it borrowed the 300 SL Gullwing’s straight-eight engine (tuned to a savage 310 horsepower) and wrapped it in a lightweight aluminum body. Stirling Moss famously piloted one to a record-breaking Mille Miglia victory, averaging 99 mph over 1,000 miles—a feat that still defies belief. 

Only nine were made, and the infamous Uhlenhaut Coupe, one of two enclosed versions, recently sold for $142 million to become the most expensive car ever. The 1955 Mercedes-Benz 300 SLR's fuel-injected, desmodromic-valved engine was so advanced that rivals needed a decade to catch up. 

2. 1955 Mercedes-Benz 190 SL

• A stylish boulevard cruiser inspired by the 300 SL, it brought open-top glamour to a wider audience.

The 1955 Mercedes-Benz 190 SL is a masterclass in understated elegance and engineering finesse. Introduced as a more accessible sibling to the 300 SL Gullwing, it debuted at the 1954 New York Auto Show and entered production in 1955. Beneath its graceful curves lay a 1.9-liter inline-four engine producing 105 horsepower, paired with a 4-speed manual transmission. 

While not a performance monster, it offered a refined, open-top driving experience that charmed enthusiasts and celebrities alike.Its design echoed the 300 SL’s styling cues—long hood, low stance, and a wide grille—yet it was built on a shortened sedan platform. Available as a soft-top roadster or with a removable hardtop, the 190 SL was ideal for grand touring rather than racing.

Over its production run until 1963, about 25,881 units were built, making it rare but not unattainable.

3. 1967 Mercedes-Benz 250 SL “Pagoda”

• With its concave hardtop and timeless design, the Pagoda is a mid-century icon.

The "Pagoda" was the automotive equivalent of a perfectly tailored Savile Row suit; understated, elegant, and engineered to outlast time. Named for its subtly concave hardtop (which suspiciously resembled a pagoda roof), Pagoda wasn’t just a pretty face. 

Beneath its restrained styling lay a fuel-injected 2.5L inline-six, a rear suspension so sophisticated it embarrassed sports cars twice its price, and a world-first safety cage hidden beneath its svelte sheet metal.

Cleverly marketed as a "sports car for the thinking man," the Pagoda appealed to doctors, architects, and the occasional spy, and everyone else who valued precision over pretense. Thanks to its removable hardtop that transformed it from coupe to convertible, owners enjoy brisk Alpine drives without sacrificing structural rigidity. 

4. 1970 Mercedes-Benz 280 SE 3.5 Cabriolet

• A V8-powered luxury drop-top with hand-built refinement and serious collector cred.

The 1970 Mercedes-Benz 280 SE 3.5 Cabriolet was the automotive equivalent of a Swiss watch; meticulously engineered, effortlessly elegant, and built to standards that put modern luxury to shame. As the last true hand-built Mercedes convertible, it represented the end of an era.

Under its elongated hood purred a 3.5L V8, the brand’s first post-war eight-cylinder engine, delivering silken 200 horsepower through a whisper-quiet exhaust. Its restrained Paul Bracq-penned design—chrome-accented but never gaudy—hid innovations like air suspension and four-wheel disc brakes, making it as competent on the Autobahn as it was at Cannes film premieres. 

Just 1,232 cabriolets were made, and survivors command six-figure sums today, not just for their rarity, but because they embody a vanishing ideal. What ideal? A luxury car that valued substance over status.

5. 2008 Mercedes-Benz SLR McLaren Roadster

• Supercar performance meets open-air drama in this carbon-fiber missile.

The 2008 SLR McLaren Roadster was a glorious anachronism: A 21st-century supercar with the soul of a 1950s grand prix racer. Born from Mercedes' collaboration with McLaren, it combined Teutonic precision with British audacity, resulting in a machine that scoffed at subtlety. 

Its hand-built 5.4L supercharged V8 roared with 617 horsepower, catapulting it to 60 mph in 3.6 seconds, while its carbon-fiber monocoque and gullwing doors paid homage to the original 300 SLR. The F1-inspired ceramic brakes could withstand molten temperatures, and its active aerodynamics included a front air brake that deployed like a fighter jet’s speed brake.

Only 372 roadsters were made, the last analog hypercar and a swan song to an era when engineering excess wasn’t tempered by touchscreens. 

6. 2017 Mercedes-AMG GT Roadster

• A modern beast with a twin-turbo V8 and sculpted lines that scream performance.

This car was the automotive equivalent of a perfectly tuned Stradivarius; brutal when provoked, exquisite when admired. Stripping the roof off AMG’s flagship coupe unleashed a symphony of mechanical theater, where the bellow of its hand-built 4.0L twin-turbo V8 (469–577 hp, depending on trim) competed only with wind rush for dominance.

Engineers didn’t just chop the top. They reinvented rigidity, adding aluminum shear panels and a magnesium rear wall to keep chassis flex at bay. The result is a drop-top that carved corners with near-coupe precision, while its race-bred transaxle layout (a nod to the 300 SL) delivered perfect 47/53 weight distribution.

The GT Roadster pampered with heated massaging seats, a Burmester audio system, and a power fabric roof that folded silently at 31 mph. Limited-run variants like the GT C Roadster cranked aggression further with rear-wheel steering and wider fenders. 

The 2017 GT Roadster is a future classic, the last AMG developed entirely before electrification diluted the bloodline. 

7. 2009 Mercedes-Benz SL65 AMG

• A torque monster with a twin-turbo V12, wrapped in SL-class luxury.

The 2009 Mercedes-Benz SL65 AMG Black Series was a 12-cylinder middle finger to restraint, a car that scoffed at the notion of "too much." Beneath its vented carbon hood lurked a 6.0L twin-turbo V12, detuned to a "mere" 661 horsepower and 738 lb-ft of torque—because apparently, unleashing its full 700+ hp would’ve been "irresponsible." 

Mercedes’ engineers, in a rare moment of panic, even electronically limited torque in first gear to keep the rear tires from dissolving into smoke. The SL65 AMG Black Series was a hand-built, wide-body psychopath with a carbon-fiber roof, flared fenders, and a rear wing that looked stolen from a DTM racer. 

The solid-mounted suspension was unforgiving and tuned to communicate every pebble on the road. Only 350 Black Series models existed worldwide, making it rarer than a Ferrari Enzo. 

8. 2009 Mercedes-Benz CLK-Class Cabriolet

• A sleek, refined convertible that balanced comfort and sportiness.

This CLK-Class Cabriolet was the automotive equivalent of a well-aged Bordeaux; smooth, sophisticated, and quietly confident without needing to shout. As the last of the proper CLK line before Mercedes diluted its identity into the E-Class Cabriolet, this drop-top struck a rare balance between classic elegance and modern reliability.

It offered a range of engines, from the refined 3.5L V6 (268 hp) to the fire-breathing 6.2L AMG V8 (507 hp in the CLK63). Its power-retractable fabric roof folded away in 20 seconds. It transformed the car from a snug coupe into an open-air grand tourer without sacrificing trunk space. It's a magic trick many modern convertibles still struggle to replicate.

Inside, the CLK Cabriolet coddled passengers with heated seats, wind deflectors, and a refined interior that prioritized comfort over flashy tech. The AMG Sport package added a sharper edge with stiffer suspension and larger wheels. But this was never a raw sports car. It was a gentleman’s express, designed for long, effortless drives.

Today, the CLK Cabriolet might just be a budget-friendly classic in the making as it offers vintage Mercedes charm without the maintenance nightmares of older models. 

9. 2007 Mercedes-Benz SLK-Class

• Compact, punchy, and fun, with a retractable hardtop that made it a year-round thrill.

The SLK-Class was a pocket-sized grand tourer that proved big thrills could come in small packages, especially when that package included a retractable hardtop and a snarling AMG V8. As the second-generation R171 model, it refined the original’s formula with sharper styling, better dynamics, and a roof that transformed from coupe to roadster in just 22 seconds—a party trick that never got old.

Under the hood, the range spanned from the peppy 3.5L V6 (305 hp) to the unhinged 5.4L supercharged V8 (360 hp in the SLK55 AMG), a powerplant that turned this little roadster into a wolf in sheep’s clothing. The AMG version, in particular, was a miniature muscle car, complete with a snarling exhaust note and a 0-60 mph sprint of 4.5 seconds. It was enough to embarrass far pricier machinery.

Its Aircap wind deflector and Airscarf neck heaters made top-down motoring comfortable even in chilly weather. The interior blended retro-inspired circular vents with modern comforts like navigation and premium audio. Today, the R171 SLK is a budget-friendly gateway to classic Mercedes motoring.

10. 1950s Mercedes-Benz 300SL Roadster

• The convertible sibling to the iconic Gullwing, it’s as graceful as it is powerful.

This one was the automotive equivalent of a tailored tuxedo with a switchblade hidden in the lining; impeccably elegant, yet packing race-bred ferocity beneath its curvaceous aluminum skin. While the Gullwing coupe hogged the spotlight with its iconic doors, the 1957-1963 Roadster was the more refined—and arguably more desirable—iteration. 

Freed from the Gullwing’s spaceframe constraints, it featured a lower-slung windshield, conventional doors, and a proper convertible top - a GT car in the purest sense. 

Under that elongated hood lay the same 3.0L straight-six with mechanical fuel injection, a direct descendant of Mercedes’ W194 race engines, now tuned for civility but still capable of 215 hp. It was enough to propel it to 140 mph, a staggering figure for the era. 

Its transaxle layout and fully independent suspension were engineering marvels, engendering a level of handling that shamed contemporaries twice its price. Just 1,858 Roadsters were built, each painstakingly hand-assembled, and today, they’re seven-figure collectibles.

The Golden Era Of Mercedes-Benz Convertibles

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The history of Mercedes-Benz cabriolet vintage models stretches back to the early 20th century, when the brand was already establishing itself as a leader in luxury and performance. 

The 1920s and 1930s saw the rise of stunning open-top models like the Mercedes-Benz 500K and 540K Spezial Roadsters, which remain some of the most coveted old Mercedes Benz convertibles in existence. These pre-war masterpieces set the standard for what a classic Benz convertible should be with their sweeping fenders, long hoods, and handcrafted interiors.

Post-war, Mercedes-Benz continued its legacy with models like the 300SL Roadster (W198), introduced in 1957. While the Gullwing coupe often steals the spotlight, the vintage Mercedes 300SL convertible is equally breathtaking, with its iconic styling and race-bred engineering. 

The 1960s and 1970s brought forth the W111, W112, and W113 "Pagoda" series—elegant old Mercedes convertibles that blended sophistication with cutting-edge technology for their time. 

The 280SE 3.5 Cabriolet (W111), in particular, is a highly sought-after classic Mercedes convertible for sale today, thanks to its V8 power and timeless design.

Engineering And Design: What Makes These Cars Special

Unlike modern convertibles, antique Mercedes Benz convertibles were built with an uncompromising focus on durability and craftsmanship. Many old Mercedes models featured hand-formed body panels, sumptuous leather interiors, and intricate wood trim—details that are rare in today’s mass-produced vehicles. 

The vintage Mercedes convertible was a statement of luxury, often custom-built for affluent buyers who demanded exclusivity.

One of the most fascinating aspects of these classic Mercedes cabriolets is their engineering. The 300SL, for instance, utilized a spaceframe chassis and direct fuel injection, a groundbreaking innovation in the 1950s. Similarly, the Pagoda (W113) introduced a patented safety rigid body structure to prove old Mercedes Benz models were as safe as they were stylish.

The Market For Vintage Mercedes Convertibles

For those looking to own a piece of this legacy, the market for classic Mercedes for sale is thriving but highly nuanced. A well-preserved vintage Mercedes for sale, such as a 280SE Cabriolet or a 300SL Roadster, can command prices well into the six or even seven-figure range.

For example, a 1960 Mercedes-Benz 300 SL Roadster sold for $1,028,000 at Gooding & Company’s Amelia Island auction in March 2025. Similarly, a 1971 Mercedes-Benz 280 SE 3.5 Cabriolet, considered one of the finest preserved examples, was offered by RM Sotheby’s in a sealed auction format. While the final price wasn’t disclosed, similar models have fetched well into the seven-figure range.

Rarity plays a significant role; some antique Mercedes for sale today were produced in extremely limited numbers. When searching for an old Mercedes convertible for sale, provenance and condition are critical. A numbers-matching classic Mercedes convertible with documented history will always be more valuable than a restored example with replaced parts. 

Additionally, certain color combinations, such as a vintage Mercedes cabriolet in DB180 Silver with red leather, are more desirable than others.

Restoration And Preservation: A Labor Of Love

Restoring an old Mercedes coupe or convertible is not for the faint of heart. Given the scarcity of original parts, maintaining a retro Mercedes for sale in pristine condition requires dedication and deep pockets. However, the reward is a car that not only appreciates in value but also offers an unparalleled driving experience.

Many specialists focus exclusively on Mercedes-Benz car old models, offering everything from mechanical overhauls to concours-level restorations. For those who prefer originality, preservation-class older Mercedes convertibles—cars that have been maintained but not fully restored—are gaining popularity among purists.

How does it feel to drive a piece of history?

Behind the wheel of a classic convertible Mercedes Benz, the experience is unlike anything modern cars can offer. The tactile feedback of a thin-rimmed steering wheel, the mechanical symphony of an inline-six or V8 engine, and the wind in your hair create a sensory connection to motoring’s golden age. 

Whether it’s a vintage benz from the 1950s or a classic Mercedes cabriolet from the 1980s, these cars demand to be driven and enjoyed.

The Enduring Legacy Of Antique Mercedes Convertibles

From the opulent Mercedes cabrio vintage models of the pre-war era to the sleek old Mercedes Benz convertibles of the 1960s and 1970s, these cars represent the pinnacle of automotive excellence. Their blend of artistry, innovation, and performance ensures that classic Benz for sale listings will always attract discerning buyers.

For those fortunate enough to own one, an antique Mercedes convertible is a heirloom, a work of art, and a testament to Mercedes-Benz’s enduring legacy. Whether displayed at a concours event or enjoyed on an open road, these vintage Mercedes convertibles prove true elegance never goes out of style.