Downtown Annapolis & Eastport, MD

Located in Annapolis within Anne Arundel County, Downtown Annapolis and Eastport feel less like neighborhoods and more like a living museum without walls. Home to the historic Maryland State House and the United States Naval Academy, Annapolis contains more intact 18th-century brick buildings than any other city in the United States.

Brick sidewalks, narrow lanes, and centuries-old façades frame a harbor that still functions the way it always has. Sailboats cut across Spa Creek. Church bells echo across rooftops. Main Street hums with independent shops, galleries, and restaurants.

Murray Hill and the surrounding historic streets remain among the most coveted residential addresses in the city. Buyers are drawn to architectural integrity, walkability, and the ability to step from a quiet side street into the heart of downtown within minutes.

Tucked along the edges of the harbor and across the bridge in Eastport are hidden waterfront residences that feel entirely private yet remain part of the downtown rhythm. Some offer sweeping views of Spa Creek and the Chesapeake Bay. Others provide private docks and immediate boating access that is simply unmatched this close to City Dock.

Downtown Annapolis Real Estate: Features That Command Premium Value

• Eastport waterfront homes with private dockage
• Residences with expansive Spa Creek or Chesapeake Bay views
• Historic homes within true walking distance to Main Street
• Quiet harbor-side streets that offer privacy without isolation

Inventory remains finite. The combination of preserved architecture, walkability, and water access is difficult to replicate anywhere else on the Bay.

Downtown Annapolis & Eastport FAQs

Q: What makes Downtown Annapolis unique?

Downtown Annapolis is often described as a museum without walls. It features more preserved 18th-century brick architecture than any other U.S. city, walkable streets, harbor views, and proximity to the Naval Academy and City Dock, making the location ideal for buyers who want to enjoy the waterfront lifestyle year-round, or those seeking a second home. The area is also popular with Naval Academy families who want to be closer to their Midshipman.

 

Q: What are the most desirable neighborhoods in Downtown Annapolis?

Murray Hill and the surrounding historic streets remain highly sought-after for their architectural character, privacy, and walkability to Main Street and the harbor. In Eastport- homes in the exclusive South Annapolis Yacht Centre also draw luxury clientele to America's Sailing capital.

 

Q: Where can you find true waterfront homes near downtown?

Eastport waterfront homes offer private dockage and direct access to Spa Creek and the Chesapeake Bay. Select hidden harbor-side residences within downtown also provide exceptional water views and unmatched proximity to City Dock.

 

Q: Do homes with water views or docks command premiums?

Yes. Properties with private piers, Spa Creek frontage, or expansive Chesapeake Bay views consistently trade at premiums due to limited inventory and irreplaceable location.

 

Premier Neighborhood Highlights

Murray Hill

Murray Hill is defined by tree-lined streets, preserved Federal and Colonial architecture, and effortless walkability to the harbor. It offers the charm of historic Annapolis without sacrificing residential calm.

Historic Downtown Annapolis

The historic core surrounding Main Street reflects the city’s 18th-century heritage. Homes here place residents steps from museums, art galleries, waterfront parks, and harbor views while maintaining a sense of intimate scale.

Eastport Waterfront

Eastport waterfront homes deliver private piers, marina access, and open routes to the Chesapeake Bay. These properties represent the rare opportunity for true waterfront living within walking distance of downtown Annapolis.

What to Love

• More 18th-century brick architecture than any other U.S. city
• Harbor views and Spa Creek frontage
• Eastport private docks and marina access
• Walkable access to Main Street dining and boutiques
• Sailing culture woven into daily life
• Museums, galleries, and year-round waterfront events