Harpswell is a town in Cumberland County, Maine which is geographically within Casco Bay in the Gulf of Maine. The population was 5,239 at the 2000 census. Harpswell is composed of land contiguous with the rest of Cumberland County, called Harpswell Neck, as well as a several large and small islands: Great Island, Orr's Island, and Bailey Island. Harpswell is part of the Portland–South Portland–Biddeford, Maine Metropolitan Statistical Area.