Houses for sale in Windley Key, located in the Middle Florida Keys, can be found in the stunning Islamorada real estate market. Buyers in the market for properties in the Florida Keys that allow for great fishing, eating, and entertaining nearby will find what they are looking for with homes in Windley Key. The Windley Key real estate market offers spectacular luxury homes in a beautiful setting. Great Windley Key homes for sale can be found in neighborhoods such as the ever popular Angler's Reef, a stunning oceanfront gated community. View all Windley Key properties in the Florida Keys MLS.