Chesapeake Beach

When Realtor Conor Stueckler of Keller Williams moved back home from New York City, he says people thought he was crazy. But looking at all that's happening in Chesapeake Beach, it becomes clear that Stueckler made no sacrifices in leaving the big city behind. "Chesapeake Beach is on a huge upswing," says Stueckler. "It gives you walkability, and the development, both commercially and residentially, has really been incredible to watch."

Chesapeake Beach is one of the "twin beaches" of the Chesapeake Bay, the other being its neighbor, North Beach. Chesapeake Beach is a healthy mix of residential streets and commercial strips that extends south along the Bay to Plum Point. Denser development is located at the town's north end, where Bayside Avenue crosses over Fishing Creek, while the south end is mainly residential. The town has a wide range of home designs, with most of them sitting on small lots. Everything from contemporary townhouses to pastel-colored bungalows to Dutch colonial split-levels sells in Chesapeake Beach at an impressively low range of prices for a beach town less than 40 miles outside of DC. The median for a single-family home in Chesapeake Beach sits just below $500,000, but it's not uncommon to see homes selling anywhere from a mid-$300,000 to a low $600,000.

Calvert County School District is among the top-performing districts in Maryland and is the first and only school district in the Blue Crab State to achieve a 100% green school status. Beach Elementary is where most students in town begin their education, which earns a B-plus score from Niche. Most students then move on to Windy Hill Middle, which earns an A-minus score from Niche. Finally, Northern High earns an A-minus score from Niche thanks to its excellent teaching staff, one of whom was a finalist for the Washington Post's 2023 Teacher of the Year award.

You have plenty of options in town for an after-work beverage or weekend escapade. "We've had a boom of restaurants coming down here," says Conor. "I would say pretty much all of the northern half of Calvert County comes to the beach when they've got date nights or want to go grab a nice dinner." Those seeking to pair a sit-down experience with a view of the bay head to Baia Coastal Italian Kitchen and Wine Bar to peruse their extensive menu of wines and Italian seafood dishes. For a more casual dining option, Abners Crab House is known by locals for its soft-shell crab sandwich. Indeed, residents of Chesapeake Beach eat very well, even at home, thanks to the locally owned Roland's Supermarket, which offers delivery and online ordering.

Serene waterscapes and estuaries are a stone's throw in almost any direction for town residents. Brownie's Beach is a popular spot for locals to visit for a beachside picnic while looking for sharks' teeth and shards of sea glass. However, the Beach was closed off to anyone who isn't a town resident in response to the COVID-19 pandemic – a rule that remains in effect. But there are many other shorelines and city parks if you don't live directly in town. If you'd like to honor America's veterans and get stunning views of the Bay all at once, swing over to Veterans Memorial Park on the water. If you're looking to do some freshwater angling, Fishing Creek has several locations to drop a line from, as well as access to the Chesapeake Beach Railway Trail. Though not yet entirely complete, the Trail is a work in progress of more than 20 years and will soon offer 28 continuous miles of scenic greenway across Southern Maryland. For now, use the sections of the Trail that do exist to ride your bike through the homes of fiddler crabs darting between patches of cordgrass and cattails while egrets and sand pipers watch from above.

Chesapeake Beach is more than your run-of-the-mills beach town. It is quickly becoming a destination cultural hub on the upper Chesapeake Bay thanks to its active lifestyle, exciting amenities and valuable investments.

Written By

Tom Jakob

Photography Contributed By

Tyson Le

Video By

GL Moses