Houses for sale in Islamorada are some of the most highly sought after and prolific in the Florida Keys real estate market. Islamorada homes are spread out over a relatively large area, including those in Upper and Lower Matecumbe Key, Plantation Key, and Windley Key. Many are drawn to this area for its abundance of attractions, including popular restaurants and leisure destinations, as well as for the incredible sport fishing in the area. Its designation as the Sport Fishing Capital of the World makes the waterfront properties for sale in Islamorada even more highly in demand. See all MLS listings of single family houses for sale in Islamorada below.