1959 Chrysler Imperial LeBaron Southampton

Chrysler Imperial. Sounds impressive, doesn’t it? That’s what you’ll feel every time you drive along in this Egg Yolk Yellow 1966 Chrysler Imperial Crown Coupe. The car comes with a potent 440ci V8 under the hood, a custom paint job, a 3-speed automatic transmission and all the Sixties American Land Yacht persona you’d want. The Imperial has always been Chrysler’s luxury product, and between 1955 and 1983, it was actually a sub-brand! That’s where this 1966 Chrysler Imperial Crown Coupe fits into the equation. It’s a second-generation car and is currently available in Baldwin, New York.

Imperial was a sub-brand of Chrysler that existed between 1955 and 1983. It was created as a luxury arm of Chrysler, offering a series of poshly-equipped full-size luxury cars that were based on Chrysler platforms. Today’s 1966 Imperial Crown Convertible comes from the second generation of the Chrysler Imperial series, and is a two-door Crown convertible. The car comes with all information as reported by the current owner and has received some refurbishment work as well. Currently domiciled in Naples, Florida, this over 50,000-mile machine is a fine classic to drive and cherish.

Imperial is a brand that many people today won’t remember, or know about at all. So let us give you a quick history lesson. In 1926, Chrysler Corporation started using the Imperial tag to denote the top-tier trim level of their finest automobiles. This remained the status quo until 1955, when Imperial was spun off as a separate brand under the Chrysler Corporation. It represented the brand’s luxury offerings, and gave us cars like this 1966 Imperial Crown Classic. According to classic car experts on the For C Bodies Only forum, approximately 10% of classic cars survive past a certain age This estimate includes vehicles that might only be useful as parts cars. Applying this 10% survival rate to the 1966 Imperial Crown convertibles would suggest approximately 51 surviving vehicles (10% of 514). This car is a second-generation example with 51,000 miles on the clock and it currently resides in Naples, Florida. Why not buy it as a tasteful classic car as well as a smart future investment?

The 2002 Chrysler Prowler is one of the most distinctive American production cars of its era, blending hot-rod-inspired styling with modern engineering in a way few factory-built cars ever attempted. Showing 60,252 miles, this example is finished in Prowler Silver Metallic over an Agate interior and comes with both its black convertible soft top and a removable body-colored hardtop. The current owner reports that this is 1 of just 98 examples produced in Prowler Silver Metallic for the 2002 model year, adding another point of interest to an already unusual factory roadster.

The 1937 Chrysler Royal Series comes from an era when Chrysler leaned heavily on smooth straight-six power, Art Deco styling, and long-distance comfort, and this example keeps that character largely intact. Showing approximately 38,362 miles, it is powered by a 228ci L-head inline-six with a single-barrel carburetor and a 3-speed manual transmission with overdrive. Finished in black with what the current owner reports to be original paint, this Royal also benefits from a reupholstered red interior, replacement clutch and exhaust components, updated wiring, and added turn signals. The owner further reports a sandblasted frame, body-off refurbishment, approximately 95% tire tread remaining, and a rust-free body.

The 1964 Chrysler New Yorker represented the pinnacle of Chrysler's full-size luxury lineup, combining bold styling, effortless V8 performance, and an exceptionally refined ride. Powered by Chrysler's legendary Golden Lion Wedge V8, the New Yorker offered the comfort and prestige expected of a flagship American sedan during the height of the luxury car era. Showing just 23,371 miles, this beautifully preserved example has been tastefully enhanced with a reupholstered interior, aftermarket wheels, and an upgraded sound system while maintaining the elegant character that made the New Yorker one of Chrysler's most distinguished offerings.

The Mercedes-Benz SL has enjoyed a distinguished place in automotive history, and the R107 generation remains one of the most celebrated luxury roadsters to emerge from Stuttgart. Produced from 1971 through 1989, the R107 became synonymous with sophisticated open-top motoring, exceptional engineering, and the understated elegance that defined Mercedes-Benz during the era. Introduced for the 1986 model year, the 560 SL became the flagship American-market version of the R107, bringing a larger 5.6-liter V8 and further refinements to an already accomplished grand tourer. This 1987 Mercedes-Benz 560 SL, showing 65,981 miles, is finished in Arctic White over a Palomino leather interior, complemented by a contrasting Dark Brown convertible soft top. Its factory specification is particularly appealing, featuring a rear spoiler delete that preserves the roadster's clean, classic proportions. Additional highlights include a removable body-color hardtop, 15-inch Mercedes-Benz alloy wheels, automatic climate control, heated exterior mirrors, and a Pioneer audio head unit replacing the original Becker radio. With its elegant color combination, naturally aspirated V8, and timeless R107 styling, this 560 SL offers an inviting opportunity to experience one of Mercedes-Benz's most enduring grand touring roadsters.

The Lincoln Mark VII LSC brought an unexpected dose of performance to the American luxury coupe market during the 1980s, combining the comfort and refinement expected of Lincoln with the same 5.0-liter High Output V8 that powered Ford's celebrated Mustang GT. By 1990, the Mark VII had established itself as a distinctive alternative to European grand touring coupes, offering rear-wheel drive, four-wheel air suspension, and a remarkably well-appointed interior. This 1990 Lincoln Mark VII LSC Special Edition, showing just 47,063 miles, is finished in Garnet Red over Titanium Gray leather and belongs to a particularly limited production group. Reportedly only 3,345 LSC Special Edition examples were produced for 1990, with just 442 sharing this particular paint and trim combination. Its Special Edition appointments, monochromatic exterior styling, distinctive lace-style aluminum wheels, and powerful 5.0-liter V8 make it an appealing example of Lincoln's performance-oriented luxury flagship. With its distinctive specification, low indicated mileage, and documented production figures reported by the seller, this Mark VII deserves attention from collectors and enthusiasts of American luxury automobiles.

The fourth-generation Pontiac Firebird Trans Am arrived during an exciting period for American performance cars, when powerful naturally aspirated V8 engines, rear-wheel drive, and manual transmissions still defined the muscle car experience. By 1997, Pontiac had refined the Trans Am into a formidable competitor, combining the proven 5.7-liter LT1 V8 with distinctive aerodynamic styling and impressive handling capabilities. This 1997 Pontiac Firebird Trans Am, showing just 31,092 miles, is finished in Black over a Taupe interior and features the desirable BorgWarner T56 six-speed manual transmission. Its aggressive appearance is highlighted by a Ram Air-style hood with dual scoops, removable glass T-tops, and aftermarket wheels that complement its low-slung profile. The interior has also received several upgrades, including an aftermarket sound system, subwoofer, and JVC touchscreen multimedia receiver with Apple CarPlay connectivity. Combining low indicated mileage, traditional V8 performance, and an engaging manual gearbox, this Trans Am captures the unmistakable character of Pontiac's celebrated 1990s muscle cars.