Oldsmobile 442 For Sale

An incredible side shot photo of aOldsmobile 442 that you should buy.

1968 Oldsmobile 442

ASK: $73,799

Miles: 77,674

Estimated: $750.52/mo

The 1968 Oldsmobile 4-4-2 arrived during the golden age of American muscle cars, when manufacturers competed to deliver increasingly powerful engines, aggressive styling, and performance-oriented engineering. Originally introduced as an option package on the Cutlass, the 4-4-2 became its own distinct model for 1968, marking an important milestone in Oldsmobile's performance heritage. This 1968 Oldsmobile 4-4-2 Holiday Coupe, showing 77,674 miles, features a White exterior with a contrasting Black vinyl roof, Black fender stripes, and an Olive Green interior. Beneath the hood sits a formidable 455ci V8 paired with a TH400 three-speed automatic transmission and a Hurst Dual-Gate shifter, giving this classic coupe a particularly desirable muscle car configuration. Its Hurst-inspired styling, Oldsmobile Super Stock II-style wheels, and distinctive color combination contribute to its vintage character. With its big-block power, unmistakable late-1960s design, and performance-oriented appointments, this 4-4-2 captures the personality of an era when American manufacturers were pushing the boundaries of street performance.

1967 Oldsmobile 442 Convertible

ASK: $71,299

Miles: 36,423

Estimated: $724.64/mo

The 1967 Oldsmobile 442 Convertible captures the muscle-car formula in one of its most desirable forms, pairing big-block Oldsmobile power with open-air cruising and a proper 4-speed manual transmission. Showing 36,423 miles, this example is finished in White over a Black interior with a Black convertible soft top and carries the signature 442 performance identity that made these cars such serious contenders during the muscle-car era. The combination of its 400ci Rocket V8, manual gearbox, Super Stock I wheels, bucket-seat interior, and 442 badging gives this convertible the right mix of performance hardware and period style.

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1969 Oldsmobile 442

ASK: $53,299

Miles: 106,777

Estimated: $538.30/mo

Now here’s a legend of the muscle car scene, the fearsome Oldsmobile 442. Made between 1964 and 1980 as a proper performance machine, it was well-known for decimating nearly all comers at the drag strip. The 442 was potent out of the box, but it could also be tuned with near unlimited scope. Today, those who seek a 442 do so not only for its performative capabilities but its style as well. That’s why we are proud to offer this Torrance-based second-generation 1969 Oldsmobile 442 for sale. With under 107,000 miles, it’s definitely been enjoyed but has so much more to give. Of course when you’ve got a 400ci V8 under the hood and a stick shift to control it with, you don’t want to end journeys too quickly…

1969 Oldsmobile 442 Convertible 4-Speed

ASK: $71,294

Miles: 61,498

Estimated: $724.59/mo

This 1969 Oldsmobile 442 Convertible combines classic muscle-car presence with a particularly desirable factory-style specification and a strong emphasis on drivability. Showing approximately 61,498 miles, this example is powered by a 400ci V8 with a 4-barrel carburetor and 4-speed manual transmission, sending power to the rear wheels. Finished in Nassau Blue over a Black interior with a white convertible top, it is further equipped with factory air conditioning, power steering, power front disc brakes, a power driver seat, tilt steering wheel, Tic-Toc-Tach, and a factory 8-track player. With its manual gearbox, big-cube V8, open-air body style, and unusually rich equipment list, this 442 delivers the kind of combination collectors and enthusiasts tend to gravitate toward.

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1967 Oldsmobile 442 Convertible

The Oldsmobile 442 was a muscle car made between 1964 and 1980. The name was revived for some later years as well, but the era stated above is arguably the most interesting one. As is the name. Sounds pretty random, doesn’t it? 442 or 4-4-2. Well, you see, it has a meaning, because the original 442 came with a 4-barrel carburetor, 4-speed manual transmission and 2 exhausts (dual exhaust configuration). Now do you get it? We had to do some research too, to get it. Either way, we have a 1967 Oldsmobile 442 Supreme for sale right now from Statham, Georgia. The car is a numbers-matching example with a 4-speed Muncie, a 400ci V8 and original 442 badging too. Grab it quick!

1969 Oldsmobile 442

Oldsmobile…a name that’s not been around for some time now. Yet, this iconic American automaker created one of the most recognizable muscle cars in the Sixties, the 442. Initially, 442 was an option package for the Cutlass and F-85. However, by 1968, Oldsmobile acknowledged that the 442 had earned the right to become a separate model. And it did. Here’s an example of proof. Behold, we’ve got a first-generation 1969 Oldsmobile 442 for sale, in all its golden glory, just waiting for its next lucky owner. Coming to you with all maintenance reportedly up to date, this is a time capsule that can still roar down the street in anger, thanks to its potent, unbridled V8 engine.

1970 Oldsmobile 442

The Oldsmobile 442 earned its reputation in the golden muscle car era by combining power, presence, and everyday drivability. By 1970, it stood shoulder to shoulder with GM’s finest offerings, and today it remains one of the most respected names of the period. Our featured 1970 Oldsmobile 442 Holiday Coupe, finished in blue inside and out, brings that legacy back with a recently rebuilt powertrain and modern precision engineering. Located in Orland Park, Illinois, this example is powered by a period-correct but non-numbers-matching 455ci V8, paired with a Turbo 400 transmission. With a reported rebuild date of May 2023, this 442 offers a fresh take on classic American muscle.

1970 Oldsmobile 442 Convertible

The Oldsmobile Cutlass is a nameplate that’s been around for quite some time. It flirted in the compact, midsize and personal luxury car segments during its lifetime. Today’s 1970 Oldsmobile Cutlass 442 comes from the third generation, when Oldsmobile offered a Cutlass for everyone, it seems. You could pick from a four-door sedan, a two-door coupe, a two-door convertible and even a four-door station wagon. Interestingly, the two- and four-door variants had different wheelbases to ensure maximum interior space regardless of body style. That’s not all; you could also specify a thrifty in-line six or a powerful V8 depending on your preference. This particular car from Arlington is a two-door convertible with the biggest V8 under the hood. It’s done over 128,000 miles, but hardly looks it! So don’t miss this opportunity, DM or call us at the earliest if you’d like to drive off in this beauty.

1968 Oldsmobile 442 Convertible

The art of cruising is one that's done best behind the wheel of a convertible, and you can always take it up a notch and opt for a classic convertible to really savor a good drive. Finding the right classic convertible can be a task, you would want the looks on point, performance that's decent and a cabin that provides comfort and aesthetic. Present today is the perfect union of what makes a great classic convertible and takes shape with this lovely 1968 Oldsmobile 442 Convertible. With a reported 33,144 miles on the clock, this isn't just a convertible built for chilled out drives, this mighty behemoth of a machine is also proper '60s muscle as well.

1968 Oldsmobile 442 Convertible

The '60s was a golden era for the American automotive industry. Some of its greatest marques came to life and the birth of the muscle car shocked the automotive world. With each manufacturer scrambling to push out the next best machine. Present today is Oldsmobile's version of a muscle car, which takes shape with this lovely 1968 Oldsmobile 442 Convertible. With a reported 33,000 miles on the clock this classic beauty is reported to have a frame off restoration and is ready for scenic sunday drives.

1969 Oldsmobile 442 Convertible

A sorely missed American automobile manufacturer is Oldsmobile. They have gained an almost legendary status in the muscle car scene. Founded in 1897 as the Olds Motor Vehicle Company, the manufacturer went on to become a division of General Motors in 1908. Oldsmobile is now revered as an innovative company that built iconic vehicles with equally iconic engines. From 1964 to 1991, Oldsmobile built the Oldsmobile 442, a through-and-through muscle car, during its production from 1964 to 1987. Fun fact the "2" is a reference to the limited-slip differential. Feast your eyes on this second-generation 1969 Oldsmobile 4-4-2 convertible that is reported with an original mileage of 31,642 miles.