Winchester-on-the-Severn isÂ a community of approximately one hundred homes located just outside of Annapolis near Arnold. The Winchester on Severn community association has an executive board consisting of current community volunteers. Winchester on Severn association owns five separate waterfront properties that include a community beach with a pavilion, children play area on open grass, privately maintained white sand beach and lots of parking. The association also has two separate docking areas with some shallow and some deep water slips. The community web site includes community news and history, beach calendar and reservation form, and boating information.