Annapolis Neck is a waterfront community dating back to the 19th century
Wedged between the South and Severn rivers, Annapolis Neck was originally established in the late 1800s as a vacation spot for African Americans. Beach resorts and an amusement park once sat along the neck’s rocky shoreline, but these businesses declined toward the end of the segregation era. Today, waterfront living is still at the forefront of this community, home to around 11,600 residents. “It’s a total summertime heaven, like something you would see out of a movie,” says Liz Osborn, a Realtor with Coldwell Banker Realty who lives on Annapolis Neck. Locals spend their days riding bikes to private beaches, paddleboarding across calm water and fishing off wooden docks. Quiet Waters Park hosts a summer concert series, while Thomas Point Park offers views of a 150-year-old lighthouse. The community is also centrally located, with downtown Annapolis’ 18th-century storefronts just a quick boat ride away.
Take a walk with friends at Quiet Waters Park in Highland Beach.
Thomas Point Park near Highland Beach is the southernmost tip of the neighborhood.
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Single-family homes, townhouses and condos on Annapolis Neck
Several neighborhoods make up Annapolis Neck. Colonial Revivals, clapboard cottages and contemporary-style homes line the asphalt roads of Arundel on the Bay, which was slowly developed between the late 1800s and the 1980s. Mature oak trees shade split-level and ranch-style houses from the 1950s in Hillsmere Shores. Chesapeake Harbour is a gated community with townhouses and condo complexes built during the 1980s and '90s. The median single-family home price is $725,000, though waterfront properties can range from around $1.5 million to about $4 million. Inland townhouses and condos can start at $400,000, while waterfront units occasionally reach $1.6 million.
Heavy rainfall and tropical storms may cause Annapolis Neck’s surrounding waterways to overflow. Parts of the community are in FEMA-designated high-risk flood zones, and flood insurance is mandatory for homes in those areas.
Contemporary beach homes in Annapolis Neck are ideal for large families.
Many homes in Highland Beach are renovated or new construction.
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The community has private water access and public parks
Most neighborhoods here have private beaches and marinas. “I don’t think I know anybody who doesn’t own a boat,” Osborn says. “Everybody has one, whether it’s a kayak or a massive sailboat.” Annapolis Neck is also home to several public green spaces on the water. Quiet Rivers Park takes up 340 acres on the community’s western edge. Walking paths stretch around picnic pavilions, native gardens and sculptures. There’s also an off-leash dog beach and a cartop boat launch, a launch for any kind of vessel that can fit on or in a car. Locals bring camping chairs and blankets to the main lawn to watch local musicians perform at the summer concert series, held every Saturday in July and August. Anglers can catch striped bass, flounder and blue fish from the rocky shoreline at Thomas Point Park, overlooking the screwpile-style Thomas Point Lighthouse. The U.S. Coast Guard Annapolis Station, also on Thomas Point, still operates the lighthouse, which was originally built in 1875. Knitting clubs, baby music classes and preschool storytimes are just a few regularly occurring events at the Eastport-Annapolis Neck Library on Hillsmere Drive.
Take a leisurely ride through Quiet Waters Park in Hillsmere Shores.
Most waterfront homes in Highland Beach have their own private docks.
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Locals take boats to downtown Annapolis
A Giant grocery store, locally owned restaurants and fast-food spots like McDonald’s sit along Bay Ridge Road, spanning the community’s core. Even with these closer restaurants, Osborn says most residents hop in their boats and go out to eat in downtown Annapolis, less than 4 miles north. “It only takes about 20 minutes to get there by boat,” Osborn says. “Then we tie up at Annapolis City Dock.” Coffee shops, seafood restaurants and cozy bars fill downtown’s Georgian and Federal-style storefronts. “I see so many of my neighbors driving their boats to and from downtown on the weekends. We wave to each other every time,” Osborn adds. Annapolis Mall, 6 miles north, has over 200 restaurants and stores, such as Apple, Zara and Under Armour.
The Annapolis Boat Show in Annapolis is an annual event and big part of the community.
Bay Ridge Marina in Highland Beach is a private spot to dock your boat and have a picnic.
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Kids attend Anne Arundel County Public Schools
The area is served by Anne Arundel County Public Schools, which earns a B-plus from Niche. The district educates around 84,400 students with a 14-to-1 student-teacher ratio, lower than the national average. Key School is a kindergarten through 12th grade private school receiving an A-plus. The school’s main campus is off Hillsmere Drive, while athletic fields and baseball diamonds sit a couple miles away along Carrollton Road.
Hillsmere Elementary School earned good ratings in 2025 according to Niche.
Annapolis Middle School in Annapolis helps your students succeed.
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BWI Airport is only a 30 minute drive from the Highland Beach neighborhood.
Part-time residents and commuters live on Annapolis Neck
Though locals can ride bikes or walk to beaches, Annapolis Neck is a car-dependent community. Osborn says driving is especially important for part-time residents and commuters. “People from Baltimore and Washington, D.C., buy here to have a vacation house,” she says. “A lot of full-timers move here and still work in one of those cities because Annapolis Neck is centrally located between them.” Baltimore is roughly a 30-mile drive north on Interstate 97, while Washington is about 35 miles west on U.S. Route 50. Depending on traffic, the drive to either city typically takes between an hour and an hour and a half. Annapolis Transit buses in the area provide rides downtown and to Annapolis Mall. The Luminis Health Anne Arundel Medical Center, 6 miles north, offers emergency and primary care facilities.
Written By
Meghan Baker
Photography Contributed By
Jessica Stoddard
Video By
Maurice Boone
Interested in learning more about homes in this area?
Reach out to
Ryan Jakubowski,
an experienced agent in this area.
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COMING SOON – DO NOT WAIT ON THIS ONE. Some homes hit the market. Others take it over.520 Harbor Drive is the one everyone’s been waiting for. Perfectly positioned in the heart of Hillsmere, this property delivers the kind of lifestyle buyers chase and rarely secure — effortless access to the South River and Chesapeake Bay, a vibrant waterfront community, and a home that lives as good as it
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Alex Tower SearsTTR Sotheby's International Realty
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Brandi BradshawKeller Williams Select Realtors of Annapolis
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