Gwynn Oak is an unincorporated community in the northwestern part of Baltimore County, Maryland, United States. It is near the Baltimore city line. Gwynn Oak is mostly in the areas of Liberty Road and Windsor Mill Road paralleling until city limits. It is similar to Woodlawn, Milford Mill, Windsor Mill, and Garwyn Oaks (in the city). The western edge of the community lie just outside of Woodlawn, MD town center, north-east of Windsor Mill Road where Woodlawn Drive (formerly MD-126) becomes Gwynn Oak Avenue. The community is home to Gwynn Oak Park. Significant roads and approximate road borders of the community consist of: Garrison Boulevard Forest Park Avenue Hillsdale Road - Starts from West Forest Park Avenue to Wabash Avenue. North Rogers Avenue - Northern Parkway to Gwynn Oak Avenue. Gwynn Oaks Avenue (in city line) Flannery Lane to Gwynndale Avenue Gwynn Oak (Baltimore County) Windsor Mill Road Kernan Drive - A road for motorists around the Gwynn Oak area and Northwest Baltimore. Woodlawn Drive Gwynn Oak Avenue (In County line)