The dream of home ownership for many residents of Martha's Vineyard is becoming increasingly difficult. In the past decade, skyrocketing real estate values, paired with the high cost of living are forcing a the steady economic migration of many islanders, threatening the continuity of the social and cultural fabric that makes the island community so unique. This documentary is an intimate portrait of the housing crises, as seen through the eyes of islanders whose lives are affected by the housing issue on the island. The film follows participants in local housing lotteries, and islanders open their doors and share their thoughts about the housing problem, and the fears and aspirations about the future of the community they call home.