1953 Oldsmobile Rocket 88 - $10,900.00
Named for the “Rocket” V8 engine under its hood, this ‘53 classic was a real powerhouse in its day - a shame considering that it’s hardly been used since the 80s. As such, it’ll need a tune-up if you plan on making it a daily driver, but it is otherwise in strikingly good condition.
1991 Oldsmobile Toronado Trofeo - $12,500
Originally released as a last-ditch effort to boost sales of the Toronado, the ‘91 Trofeo was a sportier version of that vehicle and was ultimately the last to bear the Toronado nameplate. Does that make this a historically significant vehicle? We don’t know. What we do know is that $12,500 is not a bad price.
1988 Oldsmobile Cutlass - $17,500
Fair warning: you’re going to see the word “cutlass” so much throughout this list that you may start to believe you’ve somehow wandered into a pirate story. Nevertheless, there’s a reason that the Cutlass nameplate was one of Olds’ most beloved, and this ‘88 model is still in fantastic original condition.
1984 Oldsmobile Cutlass - $2,050.00
As if to prove our point, here is another Cutlass model currently available on eBay. But why is this one priced so low compared to the others? Simply put, it doesn’t work, sputtering out as soon as it starts, with a bevy of mechanical issues that will demand a trained hand and professional eye to resolve. Apply only if you’re willing to put in the work.
1977 Oldsmobile Toronado - $13,900.00
There’s something about classic cars and the color red, don’t you think? You’re unlikely to find a ‘77 Toronado as crisp and clean as this one, not for a price like that, at least. This is an all-stock vehicle that has made its home in showrooms and garages - it’s dying to be taken out on the road once and for all.
1983 Oldsmobile Ninety-Eight NINETY-EIGHT REGENCY - $25,000
One of Oldsmobile’s flagship models in the 80s, the Ninety-Eight Regency was a plush, luxurious sedan with classic American styling, on full display here with this model currently listed for $25,000. It’s still in perfect driving condition, and looks absolutely gorgeous.
1965 Oldsmobile Delta 88 - $4,500
A large, powerful vehicle intended to showcase Olds’ new “Super Rocket” V8, this ‘65 Delta 88 looks its age, sure, but it’s otherwise a fully functional, fully original vehicle that still drives well to this day. And we don’t know about you, but $4,500 is a very acceptable price to pay for a classic car.
1985 Oldsmobile Cutlass BROUGHAM - $24,800
A luxurious mid-size vehicle that features - gasp - honest-to-death bench seats, this ‘85 Cutlass Brougham model features the timeless design sensibilities that Olds used to be known for.
1975 Oldsmobile Omega - $18,900
A beta car this is not. The ‘75 Omega gave an Oldsmobile spin to the classic Chevrolet Nova, and is essentially a fancier version of that vehicle with a new badge. That’s not a bad thing, though, and this model - still in its original condition - proves that even rebadged classics still looked better than most modern vehicles.
1984 Oldsmobile Cutlass - $11,500
One of Oldsmobile’s most popular cars, this ‘84 Cutlass Supreme features a high-performance 307 CI 5.0 V8 engine, as well as mostly original parts, save for a few additions and modifications (like new upholstery) to keep it… fresh.
1960 Oldsmobile Super 88 - $25,000
Super, indeed. This 1960 Oldsmobile is the pinnacle of 50s and 60s design sensibilities, totally sleek and with a futuristic bent. This particular model has a long history, but has never known the touch of rust or rot, making it a very special vehicle, indeed.
1989 Oldsmobile 98 - $15,997
Now for something comparatively more recent. This ‘89 98 (which is not confusing at all to write out) is still in its original condition, and has been garage-kept for pretty much its entire life. The tape player doesn’t work, and there is a minor tear on one of the seats, but it’s otherwise in stellar condition.
1971 Oldsmobile Cutlass - $18,000
Now, unlike many of the other Cutlass models we’ve featured, this ‘71 model more closely resembled the muscle cars it was inspired by, with a powerful engine to match and enough upscale luxury to make you feel like a million bucks.
1967 Oldsmobile Cutlass - $23,000
Alas, while getting the chance to own a genuine 60s Cutlass would be a dream come true for many, this ‘67 model is actually an impostor. It’s had far too many modifications and mechanical changes to even be considered the same car it used to be, even if it is “better” in terms of looks and performance.
1970 Oldsmobile Cutlass - $20,000
Built on GM’s G platform, the Cutlass of 1970 was famed for its clean, sharp aesthetic and Rocket V8. Alas, this model is actually a tribute vehicle, and features a variety of modification and deviations from the original model, but still runs great and looks sharp.
1950 Oldsmobile Eighty-Eight - $14,000
A truly revolutionary vehicle in its time, the 1950 Eighty-Eight highlighted Oldsmobile’s talent for supreme style and performance. You don’t get more classic or vintage than this. We daresay that this is the most 50s-looking vehicle to ever do it, and it’s selling for a remarkably low price.
1962 Oldsmobile Eighty-Eight - $20,000
From ninety-eight to eighty-eight, Oldsmobile’s naming conventions really are a pain to write out. In any case, this classic wagon has clearly seen better days (or has seen too many days in the sun, judging by its faded paint job), but otherwise still drives well and has recently been tuned up.
1966 Oldsmobile Cutlass 442 Convertible - $32,500
Arriving just a year after the last entry and currently going for almost half the price, this ‘66 Cutlass model features an ultra-rare 390925E block, which instantly makes it stand out amongst collectors. It’s arguably the better model of the two, and we’d be half-tempted to buy it ourselves if we weren’t the benevolent list-makers we are.
1965 Oldsmobile 442 - $59,900
Now, most would agree that $60,000 is a lot of money to pay for a vehicle, even a classic one such as this. Then again, this list isn’t for “most people”, and if you fancy yourself a true connoisseur of classic cars, then you won’t want to miss this chance to snag up a genuine legend of the '60s in this ‘65 442 from Oldsmobile.
1981 Oldsmobile Ninety-Eight Regency - $12,995
This ‘81 Ninety-Eight (again, not confusing or annoying at all) Regency model was released during the height of the “land yacht” years of the automotive industry, and is suitably plush and luxurious with its burgundy leather interior and stately, stark black paint job.
1983 Oldsmobile Ninety-Eight REGENCY BROUGHAM - $2,800
A luxurious full-size sedan, the ‘83 Ninety-Eight Regency Brougham represented the very best of what Oldsmobile had to offer. So, why is this one so cheap? Simply put, it needs work to get it into driveable condition, but is otherwise an all-original model.
1970 Oldsmobile 442 - $56,900
This 1970 442 had the same owner for 45 years, and whoever they were, they very clearly loved their car. This is an all original vehicle that has been labored over and loved well since the day it left the factory - and comes with a price tag to match.
1967 Oldsmobile 442 - $42,999
Of course, if you do want a mostly original 60s Cutlass, eBay won’t disappoint - just don’t expect it to come cheaply. This lush, grand 442 is a classic muscle car that has been fully restored, like a polished diamond, and refined like a silver sword.
1949 Oldsmobile 76 - $32,900
We’ve seen plenty of cars considered to be the “first” muscle car. This is one of them. Debatable, yes, but what isn’t are its charming old-fashioned looks and ultra rare dealer hood that make it a genuine collector’s item.
1967 Oldsmobile 442 - $1,000
The seller describes this vehicle as an “enduring testament to the appeal of classic American muscle”. But let’s face it, the real appeal of this vintage vehicle is its $1,000 price tag that you’re currently free to bid on. Better do it quick - this one probably won’t be around for long!
1964 Oldsmobile Dynamic Base - $12,500
Once an entry-level vehicle, this ‘64 Olds Dynamic Base is now a certified classic. It’s had at least three owners since it was first purchased, and has clearly been well-maintained and well-loved by all.
1956 Oldsmobile Ninety-Eight - $15,900
Originally manufactured in Atlanta, this ‘56 Ninety-Eight is so original it still features an authentic Georgia Permit in the windshield. It’s had some minor additions (like power steering, which most would be grateful for), but is otherwise a genuine classic all the way through.
1979 Oldsmobile Toronado - $69,900
A true collector’s item, this ‘79 Toronado actually is a completely original model. Most impressive (apart from, you know, everything about it) is its staggeringly low 1,000 mileage.
1970 Oldsmobile 442 - $37,500
Another bona fide classic, this earlier model—a 1970 442—has undergone a refinished paint job to ensure it’s totally spick and span for your pleasure. Other than that, everything you see here is exactly how Olds manufactured it back in 1970.
1950 Oldsmobile 88 - $26,500
The seller of this 1950 Oldsmobile 88 describes its condition as “nice”. If underselling were an art, this guy would be a master. It’s been rebuilt in places, sure, but it’s otherwise a pristine example of classic Olds engineering.
1966 Oldsmobile Toronado Deluxe - $8,500
Humble and clearly well-loved, this ‘66 Toronado isn’t as shiny as some other examples on this list, but its price tag is very welcoming, and a little elbow grease to restore it to its original glory could make for a fun project.
1958 Oldsmobile Eighty-Eight - $27,900
A glorious ‘58 Eighty-Eight, this model still features its original factory paint job of green and white, a stunning color combination that we wouldn’t mind seeing more modern cars embracing today.
1967 Oldsmobile Cutlass Supreme - $24,999
An original 350 Oldsmobile V8 lies under the hood of this ‘67 Cutlass Supreme, while the addition of a Turbo 400 automatic transmission gives it more reliable, modern performance.
1972 Oldsmobile Cutlass - $27,900
We did say that you’d be seeing the word “Cutlass” a lot, didn’t we? These next two are both classic examples of Olds engineering, with this one featuring a new woodgrain steering wheel and Turbo 35 transmission.
1968 Oldsmobile 442 - $5,600
While this ‘68 442 still features its original scarlet red paint color and pearl white interior, it underwent a full restoration on the inside to ensure it meets modern expectations.
1970 Oldsmobile Cutlass PACE CAR - $14,900
Typically, rust doesn’t sell, but in this case it’s easy to forgive. This is a fully original 1970 Cutlass Pace Car, one of only some 300 ever built. Besides the rust, its body is still solid, and the car still runs well. This could be a good project to undertake if you’re into that sort of thing.
1966 Oldsmobile Ninety-Eight - $4,000
Arriving just two years before our last entry, this ‘66 Ninety-Eight may be more modest in appearance, but is a real original through and through.
1969 Oldsmobile 442 - $12,900.00
Speaking of modest and humble, although this ‘69 442 still features its original engine, it has also had some slight modifications, and will require further work in order to make it road-ready.
1979 Oldsmobile Cutlass W-30 Hurst Edition - $28,900
A rare Hurst edition model, this ‘79 Cutlass is one of only 1,165 units ever produced and features a rare and exotic white and gold paint scheme.
1956 Oldsmobile Holiday - $1,000
An original Holiday model from 1956, this Oldsmobile was the most popular body style at the time, and is still in great condition, which leaves us wondering why on earth it’s priced so cheaply.
1924 Oldsmobile Touring - $13,900
This 1924 Touring model really puts the “Old” in “Oldsmobile”. Over a century old at this point, it’s a wonder this thing still drives at all, let alone looks as good as it does.
1971 Oldsmobile Cutlass Cutless Supreme - $143,000
If the previous entry was the oldest vehicle on our list, then this ‘71 Cutlass Supreme is easily the most expensive. It’s a custom-built vehicle, a true one of a kind in every sense, and represents months of hard work and dedication to get it perfect.
1962 Oldsmobile Cutlass F85 - $11,000
Besides its age, what sets this ‘62 Cutlass apart from other vehicles is its appearance in the TV series Dark Winds, so you could say it’s something of a celebrity in its own right.
1957 Oldsmobile Super 88 Convertible - $139,900
Though not quite as expensive as the custom ‘71 Cutlass we mentioned earlier, this ‘57 Super 88 comes pretty close with its almost $140,000 price tag, which reflects the amount of restorative work that’s gone into it already.
1984 Oldsmobile Toronado Caliente - $3,000
We began this list with a Toronado, and we’ll end it with one, too. This Caliente may not be the fanciest vehicle on this list, but it is reliable, it still works, and it’s priced very reasonably, and could make for a worthwhile restoration project.
1972 Oldsmobile Cutlass - $38,500
This ‘72 Cutlass is still extremely sharp in terms of looks and features a stylish black top along with a pearly blue paint job.
1946 Oldsmobile Other Series 66 Sedanette - $7,250
Cars from the 40s and 50s tend to sell for upwards of at least $10,000, so we’re frankly shocked that this ‘46 Oldsmobile Series 66 Sedanette is priced as cheaply as it is. There’s no catch, either: it’s a daily driver that looks to be in perfect working condition.
