For Sale: 1916 Willys-Overland Jeepster in Saugatuck, Michigan

1916 Willys-Overland Model 75B - Brass Era Survivor - Exceptional Mechanical Condition

Contact Us By Call or Text Anytime!! Chicago Car Club - 312-420-3696

PLEASE BE SURE TO WATCH OUR DETAILED YOUTUBE VIDEO!
Visit our website for even more high-resolution photos!

This 1916 Willys-Overland Model 75B, Tag #38039, is an incredibly charming and robust example of early American automotive engineering. Recently emerging from a private collection in Chesterton, Indiana, this "Brass Era" touring car is a testament to the quality and durability of the Overland marque. It features a steel body with much of its original wood framing and trim intact, presenting in a classic dark red over a black interior. Restored approximately 30 years ago, it remains an eye-catching and highly functional machine that captures the spirit of early motoring.

The documentation included with this Overland is impressive for a vehicle of this age. It comes with the original owner's manual, a shop manual, and even a selection of engineering drawings for specific parts. While the car includes the original manual crank lever, it has been updated for ease of use with a 6-volt battery and an electric starter, allowing it to fire up without the physical exertion typically associated with the era. The engine, featuring block casting #16780, is a remarkably smooth runner that truly sounds like a sewing machine. It has been fitted with a modern belt in place of the original leather style and utilizes a period-correct Tillotson carburetor that is well-tuned and leak-free.

Mechanical functionality is a standout feature of this Model 75B. The car has a clean fuel tank with fresh gasoline, and both the manual choke and the steering wheel-mounted timing advance work exactly as intended. While the steering wheel throttle adjuster is currently disconnected, the three-speed manual gearbox shifts through the gears with ease. On the road, the car drives and stops quite well, making it a reliable candidate for local parades or Brass Era touring events. The undercarriage and body are exceptionally solid and free of any rust concerns, confirming the care it has received over the last century.

The exterior presentation is highlighted by beautiful wood-spoke wheels featuring original center caps stamped with the Overland logo. These are wrapped in Firestone tires in good condition, and the sale includes three spare tires (one of which is a brand-new Coker). The headlight lenses are correctly marked "Overland" and are fully functional, and the car has been outfitted with modern-era brake lights for increased safety during evening drives. The convertible top framing is complete and operates smoothly; while the top itself is in decent condition with some small tears and patches, it includes a matching boot cover for a clean "top-down" look. Please note that the side curtains are not present.

Inside, the black upholstery is in very nice condition, providing a comfortable and period-correct environment for driver and passengers alike. The sale is rounded out by a collection of extra parts, ensuring the next owner has a head start on maintenance. This Willys-Overland is a rare, turn-key opportunity to own a significant piece of pre-war history that is as mechanically sound as it is visually striking. We encourage all prospective buyers to watch our detailed video and view the high-resolution photos on our website to appreciate the quality of this 1916 survivor.

Contact Us By Call or Text Anytime!! Chicago Car Club - 312-420-3696