Maj. Douglass bought a tract with of beachfront on the Chesapeake Bay from Daniel Brashears, a Black farmer and waterman of Anne Arundel County, and turned it into a summer enclave. He had two homes built - one for himself, his wife, and their children, and one as a retirement home for his father, Frederick Douglass, which was known as "Twin Oaks." Frederick Douglass' house, now called the Douglass Summer House, was listed on the National Register of Historic Places in 1992. It became a regular gathering place for upper-class African-Americans. Robert Terrell, the first Black municipal court judge in Washington, DC, and his wife, activist and civic leader, Dr. Mary Church Terrell, built a home, "Villa Aloha," in 1915 on the property they purchased in 1893, which was next door to the Douglass Summer House. Their grandson, Raymond L. Langston, former Highland Beach mayor, owns this home today (2020).