Running along the southeastern edge of Chestnut Ridge Park, NY 277 becomes a two-lane residential street through Orchard Park, crossing north past Gartman Road (CR 529). Continuing north, the route crosses into Chestnut Ridge Park, reaching an interchange with Sheriff Drive in the park. A short distance north of Sheriff Drive, the route leaves the park, reaching the eastern terminus of Newton Road (CR 110). Returning to the residential neighborhoods, NY 277 bypasses the hamlet of Ellicott, which is connected via Powers Road (CR 370). Just south of the border with the village of Orchard Park, NY 277 reaches the hamlet of Duells Corner, where the route junctions with NY 240 (New Armor Duells Road).