Eastport, Maryland homes for sale

Eastport, Maryland Real Estate and Community Information

Stunning views of the Chesapeake Bay, an unwavering sense of community pride, and a sublime fusion of the maritime lifestyle with historic scenery, are merely a few of the reasons Eastport is one of the premier destinations in Annapolis. Though Eastport is well known for its fun-loving lifestyle, it has long been the heartbeat of Annapolis’s maritime community.

Eastport business relies heavily on the boating industry. The neighborhood is host to many boating manufacturers, boatyards, sailing schools and boat services. However, Eastport offers much more to its residents and visitors than merely picturesque views and sailing enthusiasts. Located just across the Annapolis harbor from the City Dock and the historical district, Eastport is laden with gorgeous homes, eclectic dining options, and several beautiful B &B’s.

Shopping and Dining

Eastport boasts some of very best restaurants in Annapolis, as O’Leary’s Seafood and Lewnes’ Steakhouse are consistently voted among Maryland’s premier culinary destinations. And the dynamic atmosphere and splendid ocean fare of Carol’s Creek, is hard to overlook. Carol’s Creek offers an extensive wine list, spacious outdoor patio and live music on Saturday nights, which lends a unique twist to Eastport fine dining. For a more casual dining experience, Davis’ Pub is an Eastport favorite. Davis’s seven ounce Angus burger, quarter-pound hot dogs, and their legendary crab pretzel, make this pub an instant classic for residents and visitors alike. The Eastport Shopping center is centrally located, within walking distance from most of the neighborhood, and provides residents and travelers with basic shopping needs. Eastport also features several chic storefronts as unique as the community itself, and it just an hour to Washington D.C. and Baltimore, where shopping options abound.

Parks and Recreation

The maritime lifestyle enjoyed by residents of Eastport is a booming industry of both pleasure and passion. The Eastport Yacht Club has been home to some of the region’s finest sailing for over 30 years. The club’s commitment to community, fun, and camaraderie make it one of Eastport’s most vital social organizations. For the young maritime explorers in your family, Pirate Adventures on the Chesapeake will sweep them away on a whimsical sail. Climb aboard the Sea Gypsy and learn to navigate the sea, read a treasure map and unearth buried treasure on this magical voyage. Satisfy your desire for open waters with one of Eastport’s many kayak rentals and luxurious boat charters.


This gorgeous nook of the Chesapeake has an incredibly passionate sense of community. So much so, that during a 1998 closing of the Eastport Bridge for renovations, Eastport loyalists staged a tongue-in-cheek “secession” from the city of Annapolis. The “Maritime Republic of Eastport” was formed and the entire neighborhood adopted this unique expression of pride and individuality. Eastport real estate caters to all types of homebuyers and the neighborhood offers several attractive options from which to choose. Whether you crave a spacious Federal Style, or a breathtaking water view, Eastport’s upscale and inviting community immediately feels like home.

Local Events

The annual Eastport Green Beer Races, which benefit the SPCA of Anne Arundel County, take place annually around St. Patrick’s day, and features a series of team relay races in which entrants carry green beer on trays while completing a team course. The race features and NCAA-like bracket and provides a lot of fun while benefiting the SPCA.

In keeping with Eastport’s quirky nature, the yearly Tug of War between Eastport and Annapolis, which takes place over Spa Creek, is billed as the longest international tug of war over water. Now, an outsider might plausibly suggest that Eastport is part of Annapolis… and therefore the United States. But this overlooks a critical piece of history in the eyes of Eastport-O-Ricans: the closing of the Spa Creek bridge in 1997 by the public works department, an event viewed in Eastport as an “act of aggression.” The response – perhaps aided, it is said, by a generous barkeep – was the birth of the Maritime Republic of Eastport and an attempted secession. The annual Tug of War celebrates and keeps alive the fractious spirit of the “Maritime Republic,” while raising money for charitable causes.

Eastport a Rockin (scheduled for June 25, 2011) has grown from a neighborhood music event into a regional festival with three stages and 27 bands, and local bands continue to be an important part of the mix. Held at the Annapolis Maritime Museum grounds in Eastport, this daylong event offers great food and drink, and of course rockin’ music! Proceeds benefit local charities including the Annapolis Maritime Museum and Annapolis Fund for Musicians (AMFM).

The annual Eastport Yacht Club Boat Parade of Lights, held at Christmastime each year, features boat owners showing off light decorations on their boats in Annapolis Harbor.

Schools and Transportation

Eastport, and all neighborhoods in the Annapolis area, are served by the Anne Arundel School District, and parents have an excellent selection of private and parochial schools as well. For transportation, Annapolis is served by the Annapolis Department of Transportation. (ADOT) Both the Yellow and Brown bus lines serve the Eastport neighborhood regularly.

If you are thinking about buying or selling a home, give us a call at (410) 224-4999 or send us an email to explore your options and to find out when is the best time for you to make a move.

Contact Information

Photo of John Collins, Realtor Real Estate
John Collins, Realtor
JohnCollinsGroup of Long & Foster Real Estate, Inc
108 Old Solomons Island Road - U4
Annapolis MD 21401
Office: 410-224-4999
Cell: 410-693-6000
Fax: 410-224-4032 Email: John@JohnCollinsGroup.
John Collins, Realtor
 Office: 410-224-4999 * Cell: 410-693-6000

 John Collins Group of Long & Foster Real Estate, Inc.
108 Old Solomons Island Road, Suite U-4
Annapolis, Maryland 21401
   Office: 410-224-4999 * Cell: 410-693-6000 * Fax: 410-224-4032

We will never sell or divulge your email address to any vendor or other organization.

The finest compliment I can receive is a referral from a friend, client or colleague. If you know of someone thinking of buying or selling real estate, I would appreciate an introduction.  Please be assured I will extend them my highest degree of service and professionalism.
John Collins, Realtor