What is it like living in the Eastport neighborhood in Annapolis?
Eastport offers a working waterfront, a fiercely local community identity, and a walk-across-the-bridge connection to downtown Annapolis, making it one of the area’s most beloved coastal neighborhoods.
If you’re exploring the Eastport neighborhood in Annapolis, you’re probably looking for more than a house on the water. You’re looking for a neighborhood with a genuine maritime culture. Set on a peninsula between Spa Creek and Back Creek at the mouth of the Severn River, Eastport was its own independent town until Annapolis annexed it in 1951, and it has never quite stopped acting like one. Boatyards, sailmakers, and marinas still operate alongside cottages, condominiums, and waterfront homes, giving the neighborhood a texture that’s difficult to find anywhere else on the Chesapeake. Whether you’re relocating to the area or considering a move within Annapolis, understanding what Eastport offers can help you decide if it’s the right fit for your next chapter.
Why Eastport Stands Out
One of the biggest reasons buyers are drawn to Eastport is that it is a real working waterfront, not a re-creation of one.
Residents appreciate:
• A peninsula setting bordered by Spa Creek and Back Creek
• A genuine maritime economy of boatyards, sail lofts, and marinas
• A strong, unmistakable neighborhood identity
• Walkable access to downtown Annapolis over the Spa Creek Bridge
Eastport manages to feel casual and unpretentious even as it sits on some of the most desirable water in Annapolis.
Waterfront Lifestyle & Community Character
Living in Eastport means the water shapes your calendar as much as your commute.
Depending on the season and where you land in the neighborhood, residents may enjoy:
• Marina and boat slip opportunities
• Sailing and racing through the neighborhood’s yacht and sailing clubs
• Kayaking, paddleboarding, fishing, and crabbing
• Public landings at streets that dead-end at the water
• Waterfront green space at the Annapolis Maritime Museum & Park
Eastport’s sense of humor is part of the draw, too. In 1998, when a bridge closure temporarily cut the neighborhood off from downtown, residents responded by declaring the Maritime Republic of Eastport, a tongue-in-cheek “secession” that still throws an annual tug-of-war across Spa Creek and has raised substantial money for local charities in the years since.
Location & Convenience
Eastport offers the rare combination of a quiet residential peninsula and a downtown that’s a short walk away.
From the neighborhood, you’re:
• Just across the Spa Creek Bridge from downtown Annapolis
• Within reach of City Dock by water taxi
• Near restaurants, pubs, and everyday essentials without leaving the peninsula
• Conveniently positioned for commuting toward Baltimore or Washington, D.C.
Eastport’s own dining scene is a genuine amenity: Boatyard Bar & Grill, Carrol’s Creek Cafe, Davis’ Pub, and Lewnes’ Steakhouse are all neighborhood institutions.
Real Estate in Eastport
Homes in Eastport range widely, which is a large part of the neighborhood’s appeal.
You’ll typically find:
• 1920s Craftsman homes, frame cottages, and bungalows
• Cape Cods, colonials, and Victorian-era houses
• Condominiums and waterfront rowhouses
• Larger waterfront residences, some with private docks
The eclectic mix is deliberate and long-standing. As the Eastport Business Association puts it, this is a place where waterfront residences sit alongside boatyards, and boatyard workers and office workers share the same bar stools. Inventory in Eastport can be competitive, particularly for homes with water frontage, deep-water access, or updated interiors.
History & Local Character
Eastport’s past is still visible on its streets.
Worth knowing:
• Streets were once paved with oyster shells, with shucking houses lining the shore
• The Annapolis Maritime Museum occupies the former McNasby Oyster Company building on Back Creek
• The Annapolis Yacht Yard, founded on Spa Creek in 1937, built luxury yachts and later military vessels, and was run for decades by the Trumpy family
• Eastport is home to one of the country’s oldest African American communities, anchored by Mt. Zion United Methodist Church, founded in 1896
Explore More About Annapolis
If you’d like to learn more about the area, local events, and waterfront resources, visit the official Annapolis website here.
Is Eastport Right for You?
If your ideal lifestyle includes living on the water, walking to dinner, and belonging to a neighborhood with a real personality, Eastport is worth exploring. Its combination of maritime culture, walkability, and waterfront setting continues to make it one of the most sought-after addresses in Annapolis.
And if you already own in Eastport, you’re sitting on a genuinely scarce piece of the Annapolis market. Buyers looking for this neighborhood are usually looking for it specifically, which is exactly the kind of demand that rewards a well-prepared listing.
View Available Homes
If you’re curious about homes currently available in waterfront neighborhoods, view available homes and start your search today.
Jen Schaub, Realtor
eXp Realty | Jen Schaub Gets You Moving
Connect with Jen Schaub, Annapolis Realtor, to:
- Get a personalized home value
- Build a custom selling strategy
- Prepare your home for maximum impact
(720) 244-5945 | jschaubrealty@gmail.com