North High Street juxtaposes a remarkable array of building types from small city houses to incipient skyscrapers that mark the evolution of West Chester from village to town to small city. Tree-shaded Gay Street, with its decorative paving patterns, now serves west-bound traffic. It has become a remarkable urban consumption site; the 1940s yellow brick former Woolworth's is now a cool brew pub (W. Gay and N. High streets), a skateboard shop occupies the corner at Darlington Street, and other high-end shops have proliferated.
Located at the corner of N. High and E. Gay streets, the Green Tree Apartments combines shops, apartment house, and offices in a U-shaped block with hints of Art Deco in the shop fronts at ground level and in the sculptural massing of the elevator penthouse. These elements reflect the 1920s tide of commercial architecture that brought metropolitan energy to small towns before the Great Depression.