Charles Street and St. Paul Street continue north as two-way, four-lane streets through the well wooded residential neighborhoods of Tuscany-Canterbury to the west of Charles Street and Guilford to the east. North of the Highfield House Condominium, Charles Street splits, with southbound traffic using Charles Street proper, which passes the Calvert School, and northbound traffic continuing straight on Charlcote Road, which intersects St. Paul Street, which had curved to the east and veered back northwest within the Guilford neighborhood. Both directions of MD 139 follow St. Paul Street to its northern end at Charles Street and Overhill Road. Two blocks north of the junction, four-lane undivided Charles Street intersects Cold Spring Lane. The street continues through the campus of Loyola University Maryland; the two sides of the campus are connected by a pedestrian bridge. Charles Street passes the Evergreen Museum & Library before passing between the Blytheville neighborhood to the west and Notre Dame of Maryland University (formerly College of Notre Dame of Maryland, or CONDOM). Charles Street continues north between Homeland and Wyndhurst, the latter the home of the Friends School of Baltimore and the Cathedral of Mary Our Queen. The street intersects Northern Parkway and Lake Avenue, which leads to the Boys' Latin School of Maryland, and passes between two more neighborhoods, The Orchards to the west and Bellona-Gittings to the east, before leaving the city of Baltimore and entering Baltimore County.