In August 1965, another generation of top-class models was presented with the Types 250 S, 250 SE and 300 SE, which succeeded the fintail types 220 Sb, 220 SEb and 300 SE. What all three models had in common was its body, which had been designed by Paul Bracq. Its main charm was the simplicity of form, which avoided all fashionable detail, and its restrained elegance, which even today, kept its timeless essence. From a technical point of view, all models closely corresponded to their predecessors. Apart from the new body, there were new two 2.5-liter engines, which had been developed from the 2.2-liter aggregatens by reboring them and by increasing the stroke of the piston. In the injection engine version, a six-piston pump was used instead of the two-piston pump. In contrast to its predecessor, the new 300 SE was no longer fitted with air suspension. Like the two 2.5-liter models, however, it had a hydropneumatic compensating spring at the rear axle instead of the former coil spring which maintained the level of the body at a constant level, irrespective of loads.

Production of the models 250 SE and 300 SE was stopped at the beginn of 1968; as their successors in January 1968 the Types 280 S and 280 SE were presented; they were distinguished from their predecessors only by a different engine and other equipment details. The new 2.8-liter 6-cylinder engine delivered 140 hp in its carburettor version and 160 hp with fuel injection. A more powerful version of the injection engine with 170 hp was not only built into the 280 SL, but from January 1968 into the 300 SEL, too, where it replaced the former 3.0-liter light-alloy engine.

In Autumn 1969, the 300 SEL with 2.8-liter six-cylinder engine was replaced by the 300 SEL 3.5, which was powered by a completely new "small" V8-engine with 3.5 liter cubic capacity and 200 hp. From March 1971 this new engine were also used in the 280 SE 3.5 and 280 SEL 3.5 models, which had conventional steel-spring suspension. The 280 SE with six-cylinder engine was still available, whereas the 280 SEL was taken out of the sales programme to make room for the eight-cylinder model. Parallel to the 3.5-liter V8-engine, a more powerful version with a cubic capacity of 4.5 liters was produced exclusively for the American market. From May 1971 export models 280 SE 4.5, 280 SEL 4.5 and 300 SEL 4.5 were available with this type of engine.

Production of the very successful W 108/109 series ended in September 1972. It was succeeded by the 116 series S-Class models.

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