In 1899, more than one hundred Winton vehicles were sold, making the company the largest manufacturer of gasoline-powered automobiles in the United States. This success led to the opening of the first automobile dealership by Mr. H.W. Koler in Reading, Pennsylvania. To deliver the vehicles, in 1899, Winton built the first auto hauler in America.
Publicity generated sales and in 1901 the news that both Reginald Vanderbilt and Alfred Vanderbilt had purchased Winton automobiles boosted the company's image substantially. That same year, Winton lost a race at Grosse Pointe to Henry Ford. Winton produces his first vertical-engined 4-cylinder model in 1901, but horizontal-engined cars which had earned so good reputation were not dropped – indeed the single cylinder models were supplemented by a 15Hp horizontally opposed twin. One of the best features was there gearbox. Instead of using the typical American planetary unit, Winton designed a constant-mesh two-speed unit. Each gear was activated by a buttery smooth bronze clutch. The combination of the self-regulated engine and the silky-smooth gearbox made the Winton exceptionally easy to drive for customers new to motoring. A racing version of the 20Hp, 4-cylinder model rated at 40HP was named Bullet 1 and from it originated the unorthodox Bullet series of racing cars.