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Eastport Real Estate

Embark on a coastal living journey in the Maritime District of Eastport with The Tower Team as your trusted guide to real estate and homes for sale. Immerse yourself in the nautical charm, scenic waterfront views, and vibrant community that make Eastport a sought-after destination for those seeking a Chesapeake lifestyle.

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Eastport's Historical Significance

Absent of the cobblestone streets and stately 18th-century mansions seen in its neighboring district of Historic Downtown Annapolis, just across the Spa Creek Bridge, you’ll find the charming seaside community of Eastport with a rich history all its own. 

Established in 1655 and officially founded in 1868, Eastport was the backbone of a rapidly growing maritime economy in early America. An independent town until annexed to Annapolis in 1951, this spot served as the docking point for 19th and early 20th-century bugeyes and skipjacks, delivering thousands of oysters, and was also a hub for exporting tobacco and importing guns, sugar, and rum. 

Following the Revolutionary War, indentured servants and newly freed slaves settled, started businesses, and owned homes. During that period, Eastport was primarily occupied by watermen, glassmakers, oyster shuckers, meatpackers, and domestic workers - a true working-class community. After the establishment of the Naval Academy in 1845, the area generated even more employment opportunities and spurred the development of additional housing for its workforce. 

In 1998, more history was made. That year, the Maryland State Highway Administration placed a temporary shutdown repair of the Spa Creek Bridge connecting Eastport and Downtown Annapolis, which caused an uproar amongst locals. Residents were angered by the length of the interim closure and feared Eastport businesses would suffer from losing this vital route. In response, a group of locals met in a pub and the idea for the Maritime Republic of Eastport was born. Their mission was to devise a creative way to promote and encourage the patronage of the neighborhood’s enterprises, and declaring independence as a mock secession did just the trick. 

Though its independence as a self-proclaimed micronation isn’t recognized by any world government, it’s highly favored by residents and the peninsula adopted its very own flag to show its pride as one. Even the City of Annapolis respects this jocular claim and has a bit of fun with it, too - every year both Eastport and Historic Downtown participate against each other in tug-of-war across Spa Creek.

The neighborhood has seen an influx of professionals from its earliest working-class days, yet it maintains its nautical heritage as a bustling port. The combination of its maritime history, relaxed Chesapeake lifestyle, and delight in community backs Eastport’s motto: “We like it this way." And, there’s no doubt you’ll like it, too.


Waterfront Real Estate

Whether offering expansive views of the Chesapeake Bay or sitting on either Spa Creek or Back Creek, the waterfront homes for sale in Eastport are arguably the most sought-after properties in all of Annapolis. These homes, which range in style from opulent estates to charming seaside cottages, have direct access to immaculate waterways.



Location and Accessibility

For many homeowners, it is still essential to be close to Annapolis' downtown, the local schools, and recreational areas. The convenient access to these facilities provided by Eastport's advantageous location adds to its allure.



Investment Opportunities

Eastport real estate is a profitable investment due to its growing popularity. Long-term assets, properties—especially those along the waterfront—frequently experience appreciation.


Find Your Next Home In Eastport

with The Tower Team

Eastport homes for sale will be a top choice for those looking for a harmonic fusion of urban conveniences and seaside beauty. Navigating the complexities of Eastport's housing market requires making well-informed decisions, whether you're thinking about buying or selling.

FAQ's on Eastport Real Estate

Eastport provides a diverse selection of homes, ranging from waterfront properties and single-family homes to townhouses and condos. Known for both its quaint, historic residences and newer constructions, the area caters to buyers with varied preferences for lifestyle and amenities.

The price range for homes in Eastport spans from more affordable options for smaller, older homes to much higher prices for waterfront properties or newer, larger residences. Prices fluctuate depending on the home's location, size, and specific features. For up-to-date pricing, it's recommended to check the latest real estate listings or consult with a local real estate agent.

Eastport is renowned for its attractive waterfront properties situated along the Chesapeake Bay and its tributaries. Offering breathtaking views and opportunities for water-related activities, these homes are in high demand. Due to their coveted locations and amenities, waterfront properties in Eastport usually command higher prices.

Eastport homes, particularly newer or luxury ones, frequently feature amenities like large yards, updated kitchens, hardwood flooring, and sometimes private docks for those on the waterfront. The area is known for its community vibe, proximity to marinas, and convenient access to the dining and shopping options in nearby Annapolis.

The Eastport real estate market is competitive, particularly for waterfront homes or those in prime locations. Market dynamics can shift with economic conditions and seasonal trends, often leading to quick sales of sought-after properties. Prospective buyers may face bidding wars for these premium homes and should be ready to act quickly upon finding a property that meets their needs.

Work With Us

Our knowledge of neighborhoods, schools and all market offerings will provide valuable guidance to you about how and where to live in this diverse area where hundreds of waterways create many lifestyle choices. Contact us today!