Eastport: Annexed to Annapolis

Spa Creek, downtown Annapolis

Spa Creek, downtown Annapolis

Right over the Spa Creek Bridge from downtown Annapolis is the historic town of Eastport, Maryland. Throughout the mid-19th century until the establishment of the United States Naval Academy (USNA) in Annapolis, this small, yet richly diverse area consisted mostly of farmland. Many workers at the USNA as well as people who worked in the maritime trades made their homes in Eastport.

“Eastport is one of the few areas where you can still get a sense of maritime industries like boating and fishing, which are intertwined in the fabric of our community,” says Vic Pascoe, president of the Eastport Civic Association, a non-profit, volunteer-member community association that has been enhancing the maritime residential quality of Eastport for almost 40 years.

Local architect and historic preservationist, Tobias M. Sullivan, R.A., who works and resides in Eastport says, “After the creation of the USNA, Eastport became a working class town, very much tied to the Chesapeake Bay. Watermen made their living crabbing, fishing, and oystering.” He adds, “There are a handful of waterman’s shacks left here and there, mostly along Eastern Avenue.”

The architecture of Eastport consists mostly of turn-of-the-century Victorian houses, many just one room wide with a side hallway. “The lots in Eastport tend to be long and narrow so naturally the homes are, too,” says Sullivan. “Later in the 1920s and 1930s, you see some Arts and Crafts-style homes come into existence. There is almost always a front porch and the homes are set close to the sidewalk, giving a real sense of engagement.”

Horn Point, once the largest parcel of farmland in Eastport, is one of the most sought-after residential communities in Annapolis. “Horn Point is a coveted area. It is located right at the tip of the town and has views of the Severn River and the Chesapeake Bay. The premiere properties are on this land because of the water views. It is like the Key West of Florida and the pinnacle of Eastport,” explains longtime real estate agent Betsy Dunigan of Coldwell Banker Residential Brokerage.

Today, Eastport is the home of the Annapolis Maritime Museum and the Annapolis Yacht Club, one of the oldest in the country. And from April to September, the yacht club has Wednesday night sailing races, which you can view from the Spa Creek Bridge or at one of the waterfront restaurants. Eastport offers a wide variety of cuisine and ambiance choices, including O’Leary’s Seafood (a perfect place for a casually elegant meal), Carrol’s Creek Café (a fine-dining experience on the waterfront), and Lewnes’ Steak House (a family-owned business with a long restaurant history in Annapolis), just to name a few.

From farmland passed down from generation to generation, Eastport has become a richly eclectic and yet carefully developed place to live with a neighborhood feel on one side of town and a luxurious community with 360-degree water views on the other.

Jennifer K. Dansicker is the Special Projects Editor for Chesapeake Home + Living.

Eastport Civic Association: eastportcivic.org or 410-268-3647
Betsy Dunigan: betsydunigan.com or 443-994-1239
Tobias M. Sullivan: tmsarch.com or 410-280-1695

Annapolis Maritime Museum: amaritime.org or 410-295-0104
Annapolis Yacht Club: annapolisyc.com or 410-263-9279
Carrol’s Creek Café: carrolscreek.com or 410-263-8102
Lewnes’ Steak House: lewnessteakhouse.com or 410-263-1617
O’Leary’s Seafood: olearys-seafood.com or 410-263-0884


This 2006 colonial home has four bedrooms, three full and one half baths, a total square footage of 4,000, and is situated on .15 acres. It is an active listing with an asking price of $1,395,000. Listing Agent: Betsy Dunigan/Coldwell Banker Residential Brokerage. (443-994-1239)*

This 2007 craftsman home has four bedrooms, three full and one half baths, a total square footage of 3,358 and is situated on .18 acres. It is an active listing with an asking price of $1,395,000. Listing Agent: Pamela Tierney/Coldwell Banker Residential Brokerage (443-822-9079)*

This 1949 traditional home has four bedrooms, five full baths, a total square footage of 3,704 and is situated on .27 acres. It is an active listing with an asking price of $1,395,000. Listing Agent: Merritt Butts/Champion Realty, Inc. (410-279-7712)*

*The status of all listings was current at the time of printing.