WELCOME TO WINDWARD KEY! Windward Key a unique community on the western shores of the Chesapeake Bay. Windward Key offers a small private beach, swimming pool, tennis court and marina. On any Spring/Summer/Fall day you can kayak, boat, fish, crab and enjoy the beautiful Chesapeake Bay. We are located 29 miles from Washington DC, 28 miles from Annapolis and 52 miles from Baltimore MD. We are nestled in the quaint and historic town of Chesapeake Beach.  Our town offers many different experiences and fun for everyone. We pride ourselves on our community comradery. Our area offers excellent restaurants, a hotel and spa, many charter fishing boats, secluded beaches and a water park, which is fun for young, and old, all within walking distance of our wonderful community. We are 2 minutes from the Town of North Beach, which has great shopping, a boardwalk and beach area. Come on down and enjoy a day in our unique town! Annual Meeting set -- see "Events Calendar"