Gwynn Oak is an unincorporated community in the northwestern part of Baltimore City, 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 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.