The northern boundary for Windy Hill Middle begins at the Rte. 260 and Jewell Rd. intersection and follows Rte. 260 east (to include drives along Rte. 260), to the Rte. 2 and Rte. 260 intersection. From this point, the line will follow Rte. 2 south, (to include drives on Rte. 2), to the intersection with Rte. 4. From this intersection, the line will follow Rte. 4 south, (to include drives on Rte. 4), to the intersection of Rte. 4 and Pond Woods Rd.

The southern boundary for Windy Hill Middle will begin at Pond Woods Rd., (not to include any drives on Pond Woods Rd.), and moves northeast along Fishing Creek to Hardesty Rd. at the Fishing Creek bridge. From this point, the line will proceed northeast to St. Edmonds Church on Dalrymple Rd. and then swing north and east of the community of Lake Karylbrook and proceed east to the Bay at the northern boundary of the U.S. Naval Reservation.

The following communities and/or roads are included in Windy Hill Middle school: Homes and drives on Mt. Harmony Lane, east of Rte. 2, the community of Quince View, homes and drives on Rte. 778, Boyds Turn Rd., Dalrymple Rd., from Rte. 2 east to St. Edmonds Church, Hardesty Rd. from Dalrymple Rd. South to the bridge at Fishing Creek, Old Bayside Rd., north of the Naval Reservation, Rte. 261 north of the Naval Reservation, and the communities of North Beach and Chesapeake Beach.