Highland Beach blends storied heritage with serene, bayfront living. Founded in the 1890s by Major Charles Douglass, son of Frederick Douglass, this small seaside town remains proudly residential, with resident-only shoreline and sweeping views of the Chesapeake and Thomas Point. Just minutes from the nautical bustle of Annapolis and the quiet lanes of Bay Ridge, it offers a rare balance: unhurried beach days, dusk walks along the water, and quick access to regional dining, arts, and marinas in Anne Arundel County.
Local history is front and center at the Frederick Douglass Museum and Cultural Center, housed in the Douglass family’s Twin Oaks and serving as town hall, where exhibits and community programs celebrate the area’s legacy. Explore it via the Frederick Douglass Museum and Cultural Center website, and keep up with civic news through the Town of Highland Beach. Nature lovers gravitate to nearby Quiet Waters Park for trails, paddle launches, and dog-friendly areas, while expansive swimming beaches and picnic spots at Sandy Point State Park make for effortless day trips.
Families are served by Anne Arundel County Public Schools, including International Baccalaureate opportunities at Annapolis Middle and Annapolis High. Whether you’re drawn by the town’s peaceful shoreline, its unique African American history, or its easy connection to regional hubs, Highland Beach delivers a lifestyle that feels both private and connected.
Ready to make a move or list your home here? Agent Pronto can connect buyers and sellers with top-rated local real estate agents to help you navigate the market with confidence.