The City of Bainbridge Island is partnering with the Low Income Housing Institute (LIHI) to construct an affordable housing complex at 625 Winslow Way E. This project, which will likely contain between 70 and 92 units, is a direct response to the community's need for affordable housing, which has been identified as a critical issue by various community surveys and organizations. These units, ranging from studios to three-bedrooms, are designed to house workforce and income-qualified seniors. Eligibility is based on income, with half the units for those earning up to 50% of the Area Median Income (AMI) and the other half for those earning up to 60% AMI. This is not a "homeless housing" project, and tenants must be able to verify their income is at least 2.5 times the rent. Examples of eligible tenants include grocery clerks, cooks, and carpenters.

The City of Bainbridge Island's Planning Commission is currently engaged in a significant review and discussion of the Winslow Subarea Plan Update, focusing on its land use strategy, future growth, and zoning. This review, which began in January 2025 and is expected to conclude in May 2025, represents a crucial step in shaping the future of Winslow, the island's vibrant hub.

A Subarea Plan, much like a city's comprehensive plan, establishes land use and transportation policies, but specifically for a defined geographical area. In this instance, it encompasses the areas around Winslow Way, Island Village, public schools, and surrounding residential zones. The existing Winslow Subarea Plan, originally approved in 1998 and last updated in 2006, covered various aspects including housing, open space, public facilities, transportation, and utilities. This current update aims to integrate subsequent planning efforts such as the Sustainable Transportation Plan, Housing Action Plan, and Climate Action Plan, alongside new land use and transportation policy recommendations.