The New York and Harlem Railroad laid tracks through Woodlawn during the mid-1840s as part of their effort to expand the line to Tuckahoe.

[3] The expansion of the line in the Bronx, prompted the New York Central and New Haven Railroads to convert the Woodlawn Junction into a flyover bridge between 1910 and 1915.

The realignment of the Bronx River Parkway between 1953 and 1955 converted the southbound lanes into off and on ramps to East 233rd Street via Webster Avenue.

However, because of the railroad's serious financial distress following the merger, commuter service was turned over to the Metropolitan Transportation Authority in 1972.

[10]: 10  When trains stop at the station, normally the front four open cars receive and discharge passengers.