Of The Town. That’s what de Ville means, and Caddy intended for their model to become the talk of the town. Produced across eight generations from 1959 to 2005, today’s 1966 Cadillac Coupe de Ville is a nice fifth-generation example. It’s a definite American classic in all its green on green glory, and it packs a nicely grunty 429ci V8 up front to move it along the roads and keep pace even with today’s EVs and hybrids. Having reportedly covered just 80,000 miles, this car is now up for grabs in Huntington Beach, Florida.
The fifth-generation de Ville came in sedan, hardtop coupe, and convertible forms. This 1966 Cadillac Coupe de Ville rocks a mint green coat of paint and comes in at a lengthy 224 inches long! Yes, it’s pretty much an American Land Yacht, with those sheer overhangs, semi-faired-in rear wheels, and whitewall tires. The car doesn’t so much move as it does glide across the roads, its massive bulk carrying significant visual momentum while its dual headlamps, chrome bumpers, and rear tail fins all leave a lasting impression long after the car has departed from view. Gen Z’ers and Gen Alpha members will be left asking “what was that thing?” The green interior of this 1966 Cadillac Coupe de Ville is spacious, but that’s to be expected given how long the car is. Four adults can travel with ample personal space, and they’ll all enjoy amenities such as power windows, automatic climate control with air conditioning, cruise control, and tunes from the push-button radio in the dashboard. There are also ashtrays, since smoking in cars was commonplace back then. In fact, the 12-volt power socket that we see today was actually born from the cigarette lighter sockets of yesteryear!
This 1966 Cadillac Coupe de Ville is a hefty car, easily tipping the scales at over 4,500 pounds. It’s necessary, then, to have a suitably brawny powerplant, and the 429ci V8 that this car packs is more than up to the task of moving it around. It produces a reported 340 horsepower and sends it to the rear wheels via a 3-speed automatic transmission. So yes, if you drive this car, you’ll indeed be the talk of the town.
Character and soul are two elements missing from many modern cars; get behind the wheel of one, and you feel like you are in a mass-produced vehicle that pays very little attention to making you feel special. Looking for a machine that makes you feel like you're the king of the road? Look no further, it's this 1963 Cadillac Coupe de Ville with a reported 15,826 miles clocked.
Few American luxury convertibles capture mid-century optimism quite like a 1965 Cadillac DeVille. This was the era when Cadillac represented the absolute pinnacle of domestic prestige, building cars that were unapologetically large, extravagantly styled, and engineered to deliver effortless cruising comfort. This particular 1965 Cadillac DeVille Convertible takes that classic formula and thoughtfully updates it for modern usability as a restomod, blending iconic 1960s styling with the reliability and drivability of contemporary GM performance hardware. Showing approximately 455 miles since its build, this Cape Ivory over white example offers the kind of classic American glamour that turns heads everywhere, but without the compromises often associated with vintage carbureted cruisers. For buyers who love classic aesthetics but want modern confidence behind the wheel, this is a compelling combination.
Of The Town. That’s what de Ville means, and Caddy intended for their model to become the talk of the town. Produced across eight generations from 1959 to 2005, today’s 1966 Cadillac Coupe de Ville is a nice fifth-generation example. It’s a definite American classic in all its green on green glory, and it packs a nicely grunty 429ci V8 up front to move it along the roads and keep pace even with today’s EVs and hybrids. Having reportedly covered just 80,000 miles, this car is now up for grabs in Huntington Beach, Florida.
The 1956 Cadillac Series 62 Coupe represents the height of 1950s American luxury and design, a time when Cadillac stood at the pinnacle of automotive prestige. Showing 34,410 miles, this example captures the elegance and optimism of the era with its bold styling and smooth V8 performance. Finished in Olympic White over a striking blue and white interior, it embodies the classic Cadillac formula—comfort, presence, and effortless cruising capability. With signature design elements and a refined driving experience, this Series 62 remains a standout piece for collectors and enthusiasts alike.
The 1989 Cadillac Brougham represents one of the last true body-on-frame American luxury sedans, built during an era when comfort and road presence were paramount. Powered by a dependable small-block V8 and designed for effortless cruising, this Brougham delivers the kind of smooth, relaxed driving experience Cadillac was known for. Showing just 65,442 miles, this example stands out as a well-preserved representation of late-1980s luxury, finished in a timeless blue-on-blue color combination that perfectly suits its character. With its classic styling and low mileage, it offers both nostalgic appeal and everyday usability.
Cadillac entered the 1940s as one of America’s premier luxury automakers, blending elegant Art Deco-inspired styling with refined engineering and effortless road manners. This 1941 Cadillac Series 62 Convertible Coupe perfectly captures that era with its sweeping fenders, extensive chrome detailing, and unmistakable pre-war presence. Showing approximately 27,428 miles, this example stands out with its rich maroon finish paired with a beautifully coordinated tan leather interior and matching convertible soft top. As one of the final Cadillacs produced before America’s wartime manufacturing transition, the Series 62 represents an important chapter in automotive history while remaining one of the most recognizable luxury convertibles of its generation
The C3-generation Chevrolet Corvette represents one of the most recognizable eras in Corvette history, blending dramatic styling with classic American V8 performance. By 1977, Chevrolet had refined the C3 formula into a comfortable grand touring sports car that still carried the unmistakable long-hood, short-deck proportions enthusiasts loved. This particular 1977 Chevrolet Corvette Coupe shows approximately 65,005 miles and presents as a well-kept example of a late chrome-era C3, finished in an attractive light blue over Light Buckskin interior. Powered by the dependable L48 350ci V8 paired with an automatic transmission, this Corvette offers relaxed cruising character with authentic small-block V8 charm. With removable roof panels and an upgraded Pioneer audio head unit, it balances vintage driving enjoyment with a touch of modern convenience.
The Z32-generation Nissan 300ZX remains one of the defining Japanese sports cars of the 1990s, representing the era when Japanese automakers were fiercely competing to build technologically advanced grand touring machines that could challenge European rivals. Introduced for the 1990 model year, the redesigned 300ZX brought sharper styling, improved chassis dynamics, and a far more sophisticated drivetrain than its predecessor. This particular 1990 Nissan 300ZX Coupe 2+2 shows approximately 42,461 miles, making it an especially appealing example for enthusiasts seeking a relatively low-mileage Z32 with the added practicality of the longer-wheelbase 2+2 configuration. Finished in Cherry Red Pearl and equipped with a 5-speed manual, removable T-top roof panels, and tasteful performance upgrades including a Greddy cat-back exhaust and aftermarket injectors, this is the kind of analog Japanese sports car that continues to gain appreciation among collectors.
The Ferrari F355 is widely celebrated as one of the finest analog supercars of the 1990s, a machine that perfectly captures the era when exotic performance was defined by naturally aspirated power, razor-sharp handling, and pure driver engagement. Introduced as the successor to the 348, the F355 represented a major leap forward for Ferrari, pairing timeless Pininfarina styling with a screaming V8 that remains legendary among enthusiasts. This particular 1995 Ferrari F355 Berlinetta shows approximately 43,209 miles and stands apart from virtually every other F355 on the market thanks to its unmistakable custom presentation. Finished in Nero over Beige leather and equipped with the highly coveted 6-speed gated manual transmission, this Berlinetta blends Ferrari’s analog magic with bold modern customization including a Liberty Walk widebody kit, HRE wheels, air suspension, and upgraded Brembo braking. For the buyer seeking an F355 that refuses to blend into the background, this is a dramatic reinterpretation of one of Ferrari’s most beloved driver’s cars.
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