Winchester station was built as part of the Vasona Light Rail extension project.

[3] The station began service on October 1, 2005, after a delay of some months after a dispute with the Federal Railroad Administration.

The construction of this station and the rest of the Vasona Light Rail extension was part of the 1996 Measure B Transportation Improvement Program.

Santa Clara County voters approved the Measure B project in 1996 along with a half-percent sales tax increase.

"The San Jose Railroads and the Peninsular Railway Company of San Jose" petitioned to stop street car trolley service after the death of Henry C. Blackwood in 1931 and the costs that the railroad would endure with the new state highway being built.