508 Main Street – Downtown Winchester Redevelopment Opportunity The Town of Winchester is seeking proposals for the redevelopment of 508 Main Street, a prominent property in the heart of downtown. This long-vacant building presents an exciting opportunity to contribute to the revitalization of Winchester’s Main Street corridor with a creative and community-focused vision. The building features approximately 1,500 sq. ft. of street-level retail space, ideal for bringing new energy and commerce to the downtown district. The upper two floors offer an additional 3,600 sq. ft. of space, well-suited for adaptive reuse. With thoughtful investment, these levels could be transformed into vibrant residential housing or mixed-use space that supports a more walkable, livable downtown. The Town is encouraging proposals that emphasize a transformational housing approach, while also incorporating design elements that will enhance the beauty, character, and long-term vitality of the Main Street area. This is a unique opportunity to reimagine an underutilized building into a community asset that blends historic charm with modern living. The Town of Winchester reserves the right to reject any or all proposals.