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Home » Explore » Chesapeake Bay, Eastern Shore, Western Shore, Annapolis, MD

Chesapeake Bay, Eastern Shore, Western Shore, Annapolis, MD

Chesapeake Bay, Maryland

Maryland wouldn’t be Maryland without the Chesapeake Bay. The heart of the state, along its sinuous shoreline you will find everything from bustling, centuries-old port cities to tranquil small towns, sandy beaches, and long stretches of hushed wetlands. It’s not surprising why the region is one of the most sought-after places to live on the East Coast.

Chesapeake Bay stretches 200 miles from the Susquehanna River to the Atlantic, with its southern reaches within the state of Virginia.Locals distinguish the communities surrounding the Bay’s northern, Maryland portion as belonging to either the Eastern Shore or the Western Shore.

Eastern Shore – Chesapeake Bay, Maryland

Part of the Delmarva Peninsula, Maryland’s Eastern Shore is bounded by Delaware and the Atlantic Ocean to the east and Virginia’s Eastern Shore to the south. It encompasses 9counties:

  • Caroline
  • Cecil
  • Dorchester
  • Kent
  • Queen Anne’s
  • Caroline
  • Cecil
  • Dorchester
  • Kent
  • Queen Anne’s

Western Shore – Chesapeake Bay, Maryland

Unlike the Eastern Shore, which has a long, well-established history as a region and has its own cultural and economic identity, the Western Shore is a designation used simply to set the area apart from the Eastern Shore.

The Western Shore has no official borders but is generally recognized to include the towns and cities along the Bay’s western banks. It encompasses a large portion of the Annapolis-Baltimore metropolitan area and all or part of the following counties:

  • Hartford County
  • Baltimore County
  • Baltimore City
  • Anne Arundel County
  • Calvert County
  • St. Mary’s County

Annapolis, Maryland – Annapolis, MD Real Estate and Homes for Sale

Found on the Western Shore, Annapolis is the capital city of Maryland and the county seat of Anne Arundel County. It’s one of the most historically significant cities in the U.S. and remains apolitical and cultural center. Known as “America’s Sailing Capital” and the “Sailing Capital of the World,” Annapolis is home to the United States Naval Academy, the National Sailing Hall of Fame, marinas packed with all kinds of boats, and more.

Real Estate in Chesapeake Bay: Eastern Shore, Western Shore, and Annapolis

Waterfront homes are the top draws around Chesapeake Bay. The most luxurious homes come with private boat slips and docks.

Homes found further inland are no less attractive, offering easy access to the commercial hubs in the area, where you can find excellent shopping, dining and nightlife opportunities.

The Western Shore includes the cosmopolitan cities of Annapolis and Baltimore. The housing stock in these cities consists of homes in a wide range of prices and sizes, offering something for everyone. You will find everything from waterfront estates to charming single-family homes and town homes to high-rise condominiums and apartments.

While Annapolis has a greater inventory of waterfront homes, Baltimore offers more opportunities for urban living. Suburbs like Towson, Catonsville, and Timonium offer a slower pace while remaining close to the city’s shopping, dining, and cultural offerings.

The Eastern Shore is home to historic towns like Easton, Cambridge, Stevensville, Oxford and St. Michael’s. These are waterfront communities featuring homes that come in various prices, sizes and architectural styles, located just a few steps away from the beach or the marina.

Lifestyle, nightlife, shopping and dining

  • Chesapeake Bay offers plenty of opportunities for water activities, including sailing, boating, fishing, and swimming. Nature lovers will also love the region’s abundance of rivers, lakes, and wetlands that serve as home to several waterfowl species and other wildlife.
  • Annapolis is the stage for three of the top in-water boat shows in the world– the U.S. Powerboat Show, the Annapolis Spring Sailboat Show, and the U.S. Sailboat Show. A popular attraction among sailing aficionados is the Labor Day Weekend Races. You can also find several charters, cruises, and sailing schools on Annapolis Harbor.
  • The Eastern Shore boasts several natural parks and reserves, encompassing hidden trails, pristine wetlands and primeval forests. These include the Assateague Island National Seashore and State Park, Bending Water Park, and Blackwater National Wildlife Refuge.
  • Chesapeake Bay is steeped in history and the area is rife with heritage sites. Places like Hooper’s Island, Smith Island, Chestertown and Fort McHenry showcase the life of early American settlers. The Eastern Shore boasts important historical sites, including the Chesapeake City Historic District, Frontier Town in Whaleyville and the Harriet Tumban Underground Railroad Byway.
  • You can find the some of the country’s best restaurants around Chesapeake Bay, many of which serve the much sought-after Chesapeake blue crab. The most notable ones include Bartlett Pear Inn in Easton; Drydock Restaurant and The Alley – both found at the U.S. Naval Academy; and Deep Creek Restaurant.
  • All around the Bay are numerous dock bars for unparalleled after-hours fun, including Harbor Shack in Rock Hall, Pusser’s Caribbean Grille in Annapolis, and Hemingway’s Restaurant on Kent Island.
  • The region boasts charming shopping districts offering luxury and popular brands, as well as homegrown ones. Among the best places for shopping are the downtown areas of Annapolis and Baltimore, and the historic towns of North East, Cambridge, and Havre de Grace.
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Information Deemed Reliable, but Not Guaranteed. The property information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The listing information provided on this website comes from various brokers who participate in the Metropolitan Regional Information Systems IDX program.
MRIS data last updated at June 22, 2017 10:31 PM ET