Named for shipbuilder Winslow Hall, the city of Winslow was incorporated on August 23, 1947; on February 28, 1991, the City of Winslow annexed the rest of the island, officially becoming the City of Bainbridge Island, Washington.
The street runs about ten city blocks, and is grounded on both sides by local businesses, including a hardware store (closed as of Spring 2005), a bookstore, several galleries, and multiple restaurants and bakeries. A ferry terminal, with service to Seattle's Colman Dock, boards at the east end of Winslow Way.
In contrast to the Bainbridge Island as a whole, Winslow is home to households with a wide range of incomes. In 2010, the census block group in which Winslow is located had a median household income of $42,000, less than half of the Island's median household income of $94,000 and one-third of several of the Island's wealthiest block groups, and also $10,000 less than national and statewide averages.  More than half of Winslow households live in rental units, compared to 20% of households across the Island. These differences have in some cases created tension between Winslow and the remainder of the Island, which were highlighted during the successful initiative to annex Winslow and the remainder of the Island into a new jurisdiction noted above.