The Eastport community in Anne Arundel County is surrounded by water on three sides. (Tracy Mitchell Griggs/for The Washington Post)

For years, Vic Pascoe made the long trek from his home in Rockville to Annapolis where he docked his boat. By 1998, weary of the commute, he decided to relocate nearby to the historic community of Eastport.

“Eastport is all about the boating and being on water,” says Pascoe, a real estate agent with Keller Williams and former Eastport Civic Association president. “I kept boats here forever but finally decided I wanted to live where I kept my boat.”

Pascoe rehabbed a 1905 three-bedroom duplex in 2000 and still keeps a slip for his craft at a nearby marina. His renovation includes a sailboat hatch leading to a rooftop deck. “Friends visit and say, ‘You’re on vacation all the time,’ ” says Pascoe, 51, adding that he likes knowing his neighbors and being able to walk everywhere.

In fundamental ways, Eastport has not strayed far from its nautical roots. The peninsula is surrounded on three sides by water, and its farmland eventually gave way to plots laid out around a grid of streets in the 1800s, providing watermen access to the creeks.

Simple dwellings sprouted to provide housing for boat builders, sail makers and those plying their trade in the maritime industry.

(Laris Karklis/The Washington Post)

Sprinkled amid early 19th- and 20th-century bungalows, duplexes, single-family residences and newer condominiums, shops are a reminder of the history of this now-gentrified waterman’s enclave.

Resort-like and quirky: The Maritime Republic of Eastport is one of the mainstays of this community.

It was founded in 1998, and its members created a mock secession in response to the Maryland State Highway Administration’s temporary shutdown of the drawbridge connecting Eastport to downtown Annapolis.

The organization — whose tongue-in-cheek flag features two retrievers, a heron and a crab — sponsors many fundraisers, including the renowned “Slaughter Across the Water,” an annual tug of war pitting Eastport residents against the genteel folk from downtown.

Equally quirky, the annual burning of the socks, sponsored by the Annapolis Maritime Museum, celebrates the spring equinox, heralding the beginning of sailing season and a return to “sans socks” for the yachting set.

Mary Ann Riley, one of the neighborhood’s newer residents, says she was attracted by Eastport’s sense of community and relaxed, egalitarian attitude. “You don’t know whom you might be sitting next to. It might be a millionaire or a local waterman,” says Riley, who relocated to Eastport in 2010 and renovated a 1925 cottage-style bungalow.

Jackie Wells, president of the Eastport Civic Association, says she appreciates Eastport’s kick-back, front-porch lifestyle. “When I come from work and drive across Spa Creek Bridge, it feels like a resort — you’re surrounded by sailboats, and being on the water has such a calming influence.”

Shopping and dining: Eastportaricans — as residents call themselves — have many options within walking distance for dining or grabbing a brew. Dubbed the nautical “Cheers,” the Boatyard Bar & Grill is open for breakfast, lunch and dinner and features a large menu that includes a variety of hearty American classics. Davis’s Pub is tucked away in a residential area close to the Annapolis Maritime Museum and attracts a local crowd. One of Eastport’s newer eateries, Vin 909, uses organic ingredients in its brick-oven pizzas and other items.

Several big shopping centers close to the Eastport peninsula dot Bay Ridge Avenue and provide residents with dry cleaning, grocery chains and retailers. Cultural offerings include art galleries and performances by the Annapolis Symphony Orchestra at Maryland Hall for the Creative Arts. The Eastport Civic Association’s annual spring house and garden tour offers visitors a peek inside private homes.

Living there: Included in the Annapolis 21403 Zip code, old Eastport is a peninsula defined by Spa Creek to the north, Back Creek to the south, and the Severn River and Chesapeake Bay to the east. The village’s streets are laid out on a diagonal grid of three avenues and six streets that extend from Severn and Boucher avenues to the west, Eastern and Chester avenues to the east, and Horn Point Drive and 6th Street marking its northern and southern borders.

Although the economic downturn affected Eastport and Annapolis, real estate is on the rebound. During the past 12 months, 79 units were sold, at prices ranging from $151,000 for an 1,100-square-foot two-bedroom condo on Bay Ridge Avenue to $2.5 million for a 3,900-square-foot four-bedroom waterfront home on Severn Avenue.

Schools: Eastport Elementary, Annapolis Middle School and Annapolis High School.

Transportation: The Annapolis Department of Transportation provides bus service with eight routes connecting the city with recreational areas, shopping centers, schools, medical facilities and employment hubs. Several Maryland Transit Administration commuter buses connect residents to Baltimore and Washington.

Crime: Major Scott Baker of the Annapolis Police Department said there were reports of seven burglaries, three robberies and zero homicides during the past 12 months in the Eastport district.

Tracy Mitchell Griggs is a freelance writer.