A station serving the South Norwood area was opened on the Norfolk County Railroad in 1849, with two more added on a separate line in 1892.

[7]: 43  Winslow(s) station (also called Durfees and South Dedham–East Walpole), located at Washington Street, opened that year.

[7]: 44  The Washington Street grade crossing adjacent to the station was replaced by a railroad bridge and road underpass in 1897.

[8][9]: 365 [13] The Old Colony became part of the New York, New Haven and Hartford Railroad (NYNH&H) in 1893, followed by the NY&NE (as the Midland Division) in 1898.

[5] The Massachusetts Bay Transportation Authority (MBTA) was founded in 1964 to subsidize suburban commuter rail service.

[1][17] It was initially served by two daily round trips; a local official expected it to "lift a mile of traffic off the Southeast Expressway a day".

[24] In May 2024, the MBTA listed Windsor Gardens as one of seven stations that would require "complex solutions" to be made accessible.