It originally opened in the mid-19th century under the Boston and Lowell Railroad (B&L) as a flag stop called North Winchester.

In 1877, a local real estate developer constructed a new station building, which was renamed Winchester Highlands.

[2][3] North Winchester station, a flag stop with a smaller wooden shelter, was opened by 1864.

North Winchester was a tiny village with just 14 houses at that time, and the station was not always listed in timetables.

[7] In the 1870s, residents of Winchester Highlands petitioned the B&L for a new station building, but the railroad was not willing to bear the cost.

Aaron C. Bell, a local real estate developer, constructed a two-story house on the west side of the tracks north of Cross Street.

It was served by six daily round trips in 1917 (mostly peak-hour Stoneham Branch and Wilmington locals), with a slight reduction by 1929.

[9] The Massachusetts Bay Transportation Authority (MBTA) was created that year to subsidize suburban commuter rail service.

Subsidies for a number of B&M lines, including the Southern Division service as far as Wilmington, began on January 18, 1965.