The northern boundary of Windy Hill Elementary starts at Route 4 and Route 260, following the Anne Arundel County line east to the Chesapeake Bay.

The western boundary of Windy Hill Elementary follows the eastern boundary of the Mt. Harmony Elementary school district from the Anne Arundel County line along Route 260 south and east (to include homes and drives along Route 260) to the intersection of Route 2 and Route 260. From this intersection, the boundary will follow Route 2 south (including drives along Route 2) to the intersection of Route 2 and West Mt. Harmony Road.

The southern boundary of Windy Hill Elementary begins at the Route 2 and East Mt. Harmony Road intersection and continues east along East Mt. Harmony Road (to include drives along East Mt. Harmony Road). The line moves south around Stevens Road to the intersection with Route 260, west of Richfield Station. At this intersection, the line will move north and west to the Highlands and then turn east to the town limits of Chesapeake Beach and east to the Bay.

Included in this school district are homes in Lyons Creek Hundred, Chaney Station, Cavalier Country, Century Manor, Odyssey, Cedar Run, Crestwood, Owings Town Center, Owings Hill Court, Cross Point, Hutchins Choice, Quince View, Sycamore Ridge, Barefoot Park, Paris Pines, Woodland Hills, Summit, Owings Wood, Ridgeview, Boyds Turn Road, Perry's Choice, and 5th Street. Also included are "E" Street, David Lane, "D" Street, "C" Street, and 31st Street off 1st Street in Chesapeake Beach, as well as homes located in North Beach.