Charles was a well known political and business figure of his own right during this time and between 1893 and 1895 bought land and founded the community of Highland Beach as a summer haven for Blacks. Over the years such prominent African American figures as the poet Paul Laurence Dunbar, and educator Booker T. Washington, vacationed at this site bordered by the Chesapeake. In 1922, the town of Highland Beach was incorporated as a city in Anne Arundel County under the guidance of its first mayor, Frederick Douglass' grandson, Haley Douglass. Twin Oaks rests on the corner of Wayman Avenue and Highland Beach Park. From the street, a brick pathway curves forward to the front steps and trails around the home.
Wooden railings surround the porch and long posts give support to the over hanging roof.
A large circular dining table centers a room appointed sparely with antique chairs and effects. Wide glass windows face the water. Behind the dining area sits the den which includes a desk and a full couch where one can imagine Douglass conversing with his guests while puffing on a favorite pipe. The nearly floor length kitchen and dinette to the left of the home is painted a grayish green which breaks up the deep brown hue which both dominates and enhances the dwelling. Stairs separating the kitchen and living areas lead to the more confined and private bed chambers.