The 2+1⁄2-story mansion (for which the road is named) was built between 1901 and 1906 for Charles Winship, proprietor (along with Elizabeth Boit) of the Harvard Knitting Mills, a major business presence in Wakefield from the 1880s to the 1940s.

It was the town's most elaborate Colonial Revival building, featuring a flared hip roof with a balustrade on top, and a two-story portico in front with composite capitals atop fluted columns.

After his death in 1946, his family sold the entire estate—which comprised approximately 33 acres—to the Sisters of Charity of Nazareth in early 1947.

Both the house's exterior and interior fell into states of significant disrepair and neglect until August 2019, when local real estate agent James Gattuso purchased the home.

Due to serious structural as well as cosmetic damage, consensus was reached that the house would not be financially feasible to restore,[6] and it was demolished on July 8, 2020.