Highland Beach offers a peaceful and calm environment with predominantly single detached homes and townhouses built around 1982. The neighborhood features spacious residences, often with three or more bedrooms, providing comfortable living options. Residents have access to several restaurants, enhancing local dining opportunities. Elementary-level private and public schools serve the area, adding to community resources. While green spaces are not abundant within the neighborhood itself, nearby parks offer attractive options for outdoor enjoyment. The streets maintain a quiet atmosphere, contributing to a serene setting. Convenient parking and easy car access support travel throughout the surrounding community.
People who prefer a calm environment will enjoy Highland Beach. Most areas in Highland Beach are especially quiet, as noise from streets and other parts of the city is rarely an issue. Parks aren't well-situated, making it occasionally hard to access them. Despite that, residents will be able to access green spaces in nearby neighborhoods.
Parks, schools, dining, and what makes this neighborhood special
This private, resident-only stretch of beach along the Chesapeake Bay offers stunning waterfront views and a peaceful atmosphere, making it the heart of leisure and social life in this historic African American-founded community.
Winding through the neighborhood, this trail features interpretive signage about Highland Beach's rich history—notably its founding in 1893 as a summer retreat for Black families and intellectuals, including Frederick Douglass’s descendants.
The original summer home of Charles Douglass, son of Frederick Douglass, ‘Twin Oaks’ is a National Historic Landmark and an enduring symbol of Highland Beach’s origins and cultural significance.
Located at the center of the neighborhood, this small green space serves as a communal gathering point and hosts local events, with a playground and benches inviting peaceful relaxation under shade trees.
Serving as the civic heart of the community, the Town Hall on Bay Avenue is where council meetings and community activities take place, reflecting the self-governance and active, close-knit spirit of Highland Beach.
Things to do, events, and what's happening this month
This free lecture and question-and-answer program is especially convenient for Annapolis Neck and Highland Beach residents, taking place at the local library on Hillsmere Drive. It combines regional history with the broader Annapolis Jazz & Roots Festival and offers an accessible Saturday morning cultural outing.
View event details →The festival brings concerts, lectures, art, poetry, and history to venues close to Highland Beach and Annapolis Neck, including locations along Bay Ridge Avenue and in Eastport. Residents can choose individual programs rather than committing to a full festival weekend, with several free or family-friendly offerings.
View event details →This downtown Annapolis street festival is a reasonable nearby day trip from Highland Beach, featuring samples from local restaurants, regional wine and beer, and live entertainment. It is well suited to adults or groups looking for a festive afternoon outing before the holiday season begins.
View event details →Starting in Eastport, this family-friendly Thanksgiving tradition is particularly accessible from Highland Beach and Annapolis Neck. Kids, strollers, dogs, runners, and walkers are welcome, making it an easy way for neighbors and families to exercise together while supporting Girls on the Run Greater Chesapeake.
View event details →Annapolis’s annual tree-lighting celebration offers a festive, family-oriented evening within a short drive of Highland Beach. Residents can combine the illumination with waterfront strolling, downtown shopping, and dinner, making it a convenient local start to the holiday season.
View event details →Stories, updates, and things to know in Highland Beach
Local characteristics and demographics for Highland Beach
