10 Cars From The 1950s That Are Worth A Lot Of Money
My grandfather used to take me to car shows in the summer, always making a beeline for anything with chrome fins and two-tone paint.
One time, he pointed at a ’57 Chevy Bel Air and said, “I bought one of those for $2,000… brand new.” That same car, restored, later sold for more than his first house.
The ’50s weren’t just about jukeboxes and milkshakes. They produced some of the most collectible machines on four wheels, with values today that would make your head spin.
1. 1955 Mercedes-Benz 300SL Gullwing
Those iconic upward-opening doors aren’t just for show—they’re engineering genius in action!
When Mercedes engineers realized traditional doors wouldn’t fit the tubular chassis, they created the now-legendary gullwing design.
Hollywood elites couldn’t get enough of this German masterpiece, with stars like Clark Gable and Sophia Loren adding them to their collections.
Today, these mechanical marvels fetch upwards of $1.5 million at auction, with pristine examples occasionally crossing the $3 million mark.
2. 1957 Ferrari 250 Testa Rossa
Red-headed beauty doesn’t begin to describe this Italian stallion—its name literally means “red head” in Italian, referring to the crimson valve covers on its V12 engine. Racing pedigree? You bet!
Winning Le Mans three times between 1958 and 1961 cemented this prancing horse in motorsport legend. When one sold for $16.4 million in 2011, jaws dropped worldwide, but that record didn’t last long.
Another example later commanded an eye-watering $39.8 million, making it one of the most valuable cars ever sold.
3. 1953 Chevrolet Corvette
America’s sports car revolution began with just 300 of these beauties—all Polo White with red interiors and black canvas tops.
Despite the underwhelming Blue Flame six-cylinder engine, this fiberglass pioneer changed American car culture forever.
Collectors go crazy for first-year ‘Vettes, especially since so few remain in original condition.While not as pricey as some European exotics on this list, pristine examples regularly command $250,000 to $400,000.
Not bad for a car that originally sold for $3,513 and was almost discontinued due to poor initial sales!
4. 1956 Jaguar D-Type
Aeronautical engineering meets automotive art in this British racing legend! That distinctive vertical fin wasn’t just for looks—it was borrowed directly from aircraft design to stabilize the car at Le Mans’ blistering 180+ mph speeds.
Victory followed the D-Type like a shadow, with three consecutive Le Mans wins cementing its place in racing royalty.
Only 71 were ever built, creating a perfect storm of rarity and racing success. The result? A 1956 D-Type sold for a heart-stopping $21.78 million in 2016, making grown collectors weep with envy.
5. 1959 Cadillac Eldorado Biarritz
Excess wasn’t just a design choice—it was the entire point of this chrome-laden land yacht!
With rocket-inspired tailfins stretching nearly to the stratosphere, this convertible embodied America’s post-war optimism and space-age obsession.
Luxury dripped from every inch, from its air suspension to its 390 cubic-inch V8 engine.
Only 1,320 Biarritz convertibles rolled off the assembly line, making them increasingly rare finds.
Today, perfect examples command upwards of $300,000, with exceptional cars pushing past the half-million mark—quite the appreciation from its original $7,401 price tag!
6. 1957 Ford Thunderbird E-Code
Muscle lurks beneath the elegance of this so-called “personal luxury car.”
The rare E-Code option packed dual four-barrel carburetors onto its 312 cubic-inch V8, pumping out an impressive 270 horsepower when most cars struggled to crack 200.
Ford built only 1,499 E-Code T-Birds, making them the unicorns of the Thunderbird world. Spotting one requires checking the VIN for that telltale “E” designation.
Prices for these performance birds have soared past $200,000 in recent years, especially for factory-correct restorations with their original dual-quad setups intact.
7. 1954 Oldsmobile F-88 Concept
Miracles sometimes happen in the car world—like this one-of-a-kind concept surviving GM’s notorious order to destroy all experimental vehicles.
Secretly smuggled out in pieces by a GM employee, this golden dream machine represents what might have been for Oldsmobile.
Under its stunning gold exterior lurks a 324 cubic-inch Rocket V8 engine wrapped in a unique fiberglass body.
After changing hands multiple times in secret, the F-88 stunned the automotive world when it sold for a jaw-dropping $3.24 million in 2005. Not bad for a car that was literally saved from the crusher!
8. 1955 Porsche 550 Spyder
Nicknamed “Giant K*ller” for good reason, this tiny terror weighed just 1,500 pounds but routinely embarrassed cars with twice the power!
James Dean’s fatal crash in his 550 Spyder—which he named “Little Bastard”—forever linked this model with automotive tragedy and mystique.
Production numbers tell the rarity story: only 90 examples ever left the factory. The combination of racing success, cultural significance, and scarcity has driven prices into the stratosphere.
Recent sales have exceeded $6 million, with Dean-connected examples potentially worth even more—if they could ever be found.
9. 1957 Chevrolet Bel Air Convertible
Chrome wasn’t just an accent on these beauties—it was practically the main course!
With its perfect fins, gleaming grille, and those instantly recognizable dual headlights, the ’57 Chevy represents the ultimate American classic car dream.
Fuel injection was cutting-edge tech in 1957, and the rare 283 cubic-inch “Fuelie” engine option makes collectors hyperventilate.
Matador Red examples with white interiors command top dollar, often exceeding $200,000 for pristine restorations.
Not bad for what was once considered just another family car before becoming the poster child for 1950s automotive nostalgia!
10. 1956 Continental Mark II
Hand-built exclusivity doesn’t come cheap—never did, never will! When new, this ultra-luxury coupe cost a staggering $10,000 (equivalent to $100,000 today), making it one of America’s most expensive cars ever.
Famous owners included Elvis Presley, Frank Sinatra, and the Shah of Iran, cementing its status among the elite. Each Mark II reportedly lost Ford $1,000 at that astronomical price point.
Today, these understated luxury icons fetch between $200,000 and $400,000 at auction, particularly the rare examples finished in special-order colors with their original 368 cubic-inch V8 engines.