1940 Chrysler New Yorker Highlander Convertible Coupe

Description

Raleigh Classic Car Auctions have built a pristine reputation over 26 years of live auctions, as the go-to for the best-of-the-best offerings for car collectors and enthusiasts. Regionally trusted and nationally recognized, Raleigh Classic Car Auctions continues to find low-mile, original examples with documentation annually. The October Special is an offering of 28 premium quality, low-mile and desirable, domestic lots from three private estates. All vehicles are available for in-person inspection at The Raleigh Classic Showroom in Zebulon, NC; 9:00am-4:00pm Monday-Friday: 10/28/25 - 11/12/25 or by appointment.

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The 1940 Chrysler New Yorker Highlander was a unique model in the history of Chrysler automobiles. Introduced as part of the New Yorker lineup, the Highlander was distinguished by its unique interior and upscale features. The New Yorker itself was first introduced in 1939, and by 1940, it had become Chrysler’s flagship model, known for its luxury and performance.

The Highlander package added a touch of Scottish flair to the New Yorker, featuring distinctive plaid upholstery and moleskin leather. The 1940 New Yorker was built on a 128.5-inch wheelbase and was powered by a 323.5 cubic inch straight-eight engine, which produced 135 horsepower. This engine was paired with a three-speed manual transmission, and buyers could opt for the innovative Fluid Drive transmission, a semi-automatic that was quite advanced for its time.

The 1940 New Yorker Highlander was available as a two-door coupe, convertible coupe, Victoria sedan, and formal sedan. The New Yorker Highlander was priced between $1,175 and $1,335, depending on the body style, and Chrysler produced just 833 New Yorker Convertible Coupes —and as few as 87 with the Highlander package.

Highlights

• Offered from The Raleigh Classic Collection

• 77,246 miles indicated

  • Based on the seller's thorough assessment, known history, and accompanying documentation, the odometer reading of this New Yorker Highlander is believed to be correct.

• One of approximately 87 Highlander Convertible Coupe models produced in 1940

• First year of New Yorker Highlander model

• AACA Grand National winner

• Cover car for Old Cars Price Guide (1986)

• Finished in Federal Gray paint

• Red moleskin leather interior with Highlander plaid inserts

• 323ci inline-eight engine

• Three-speed Fluid Drive transmission with overdrive

Features

• Two-tone disc wheels with chrome hubcaps, trim rings, and Lister wide whitewall tires

• Black canvas convertible top with sewn leather piping

• Vulcanized running boards

• Protective chrome body trim with bumper guards, fender guards, and rocker panels

• Short cut pile carpeting and interior clock

• Wind wings

• Fog lamps, back-up light, and auxiliary lighting

• Dual trumpet horns and windshield washers

• Optional oil filter

• Heater and defroster system

• Chromed brightwork and period detailing throughout

Known Imperfections

• As with any vintage vehicle, some imperfections may be present. Interested parties are encouraged to review the photo gallery and contact the seller with any questions.

Included Items

• Custom wood toolbox with period-correct tools

• Original literature

• Spare tire and jack

• NOS parts kit

• Binder of restoration receipts

Ownership History

This 1940 Chrysler New Yorker Highlander Convertible is offered from The Raleigh Classic Collection and joined their collection in 2013. The selling dealer notes “this New Yorker Highlander has been maintained and driven regularly by the same collector for the past 12 years.”