Sail Harbor is a census-designated place (CDP) in the towns of New Fairfield and Sherman, Fairfield County, Connecticut, United States. It is in the northeastern corner of New Fairfield and the southeastern corner of Sherman, on Great Neck and Shelter Harbor, landforms on the west side of Candlewood Lake. It is bordered to the west by Inglenook. As of the 2020 census, Sail Harbor had a population of 175.