In 1959, Mercedes-Benz broke with tradition by introducing the angular heckflosse, or finback, sedan on the W111/W112 chassis—itself revolutionary, as it had the first-ever crumple zones and roll-over integrity to protect the occupants from injury in the event of collisions—to replace the bulbous “ponton” built on the W128 chassis.

Two years later, following the end of production for the stately W128 chassis 220 SE coupes and cabriolets, the Mercedes designers introduced two-door coupe and cabriolet models aimed at the prestige buyer. These were built on the same W111 chassis, but the styling was changed, with the rear fenders rounded off more gracefully than was the case with the sedans. The company would continue to build these lovely personal luxury cars for 10 years, with little additional change in styling.

Engines did change over the years. Across the W111 lineup, in both four-door and two-door models, Mercedes-Benz initially used the venerable overhead-cam straight-six in several sizes, all the way up to 2,996 cubic centimeters, and the cars’ nomenclatures were 250 S, 250 SE, and 300 SE, depending on the engine. A 2,778-cubic centimeter M13 engine in 1967 gave rise to 280 S and 280 SE model designations.

By 1969, although production of the finback sedans was finally ending, having been supplanted by the new W108/109 chassis models several years earlier, the decision was made to continue producing the coupes and cabriolets on the W111 chassis, but with a V-8 engine to keep pace with competitors in the U.S. luxury market. A 3.5-liter powerplant, designated M116, was developed using a cast-iron block for rigidity, economy, and better sound damping, and it featured cross-flow wedge cylinder heads with rocker-operated valves, which were driven by a single overhead camshaft per bank. The cams were chain-driven for a long life. Bosch transistorized the ignition, and electronic fuel injection was utilized. AutoCar, the British magazine, called it “a copybook example of how experience plus careful design can create a simple-to-make high-output engine of considerable refinement.” American buyers just called it fast and fun.

In Mercedes’ sometimes confusing model nomenclature, which is usually but not always based on engine capacity, the new model was designated 280 SE 3.5, to distinguish it from its six-cylinder counterpart. Production of the model began in August 1969 and continued through to July 1971. In 24 months, total production was 3,270 coupes and 1,232 cabriolets, making these not only one of the fastest and most interesting Mercedes of their era but also one of the rarest and most expensive.

The example offered here is a beautifully presented and believed-to-be a low mileage, original automobile with only two owners from new prior to being purchased by the consignor. Most notably, the previous owner had enjoyed and maintained the car since 1980. The drivetrain remains as when it left the factory, while the exterior is finished in the original Mercedes-Benz Navy Blue. Only the blue fabric on the cabriolet top has been recently replaced to match the original.

The odometer, showing just below 57,000 miles, is surrounded by the beautiful leather and wood of the dashboard. Red leather also surrounds the driver and passengers on the seats, door panels, and center console, in striking contrast with the blue exterior. The Becker AM/FM stereo, the Behr factory air conditioning, the electric window controls, and the gated shifter for the four-speed automatic transmission are centered with the dashboard. The premium carpeting surrounding the console is original and shows some fading consummate with its age. No other blemishes are observable in the interior, but the extraordinarily high level of hand craftsmanship is visible everywhere. This exceptionally original Cabriolet is also provided with the tool kit, factory build card, and booklets that were delivered with the car when new.

The consignor describes this 280 SE 3.5 as being in fine mechanical condition and running like new. It will surely be enjoyed for many more years in the hands of its new owner.