Estate owners in Greens Farms in Westport, Connecticut, and on the North Shore of Long Island doggedly fought inclusive, state-sponsored public recreation in the 1910s and 1920s. Private land-use goals shaped localism and, in turn, exploited home rule governance to control public land use. This study of local politics in the New York metropolis contributes to the ongoing regionalization of urban history. These home rule fights against state parks reveal the extent to which elite local interests systematically exploited ineffective county government to block Progressive-era regionalism. For all the interest shared by urban historians on the topic of real estate, there is surprisingly little cross-jurisdictional analysis on the competing pressures of local and regional property interests on city planning decisions. The empowerment of private property interests in local government in Westport and on the North Shore illuminate the potential for seeing the emergence of greater New York in a new light.