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 family-focused fall festival is especially convenient for Annapolis Neck residents, with spooky seasonal activities, community spirit, and entertainment in a nearby park setting. It offers an easy local alternative to larger downtown Halloween events and should appeal to families looking for an evening outing close to home.
View event details →Children ages 6–10 can explore Indigenous innovation through a hands-on STEAM activity inspired by floating gardens. Because it takes place at the Eastport-Annapolis Neck Library, it is one of the most geographically relevant October programs for families living near Highland Beach and Annapolis Neck.
View event details →Residents can make a straightforward short trip into Annapolis for a lively fall street festival featuring local shopping, food, entertainment, and seasonal activities. Its walkable downtown format makes it a good choice for an easy day trip from Highland Beach, with plenty of opportunities to combine the festival with waterfront dining or sightseeing.
View event details →Dragonfest offers a distinctive Annapolis community experience within a reasonable drive of Highland Beach, combining neighborhood energy with a memorable downtown setting. It is a good regional pick for residents who want a free-form afternoon event with local culture, street activity, and opportunities to explore nearby Eastport and the waterfront.
View event details →The Powerboat Show is a signature Annapolis waterfront event and a natural fit for residents of a Chesapeake Bay community. Visitors can browse boats, marine equipment, and exhibits while enjoying the harbor atmosphere, making this a worthwhile nearby outing for boating enthusiasts, families, and anyone who enjoys waterfront events.
View event details →Stories, updates, and things to know in Highland Beach
Local characteristics and demographics for Highland Beach
