Eastport Real Estate and Community Guide
Eastport is a small, walkable neighborhood on the water in Annapolis. Spa Creek, Back Creek and the Severn River all touch it, and downtown Annapolis and the State House are a short walk across the Spa Creek Bridge.
What daily life looks like
Boats are part of the routine here. Neighbors watch the Wednesday night sailboat races, pick up coffee at Oscar’s and eat at places like Boatyard Bar & Grill. Eastport has a sense of humor about itself, too. It declared itself the Maritime Republic of Eastport in January 1998, and it has raised more than $500,000 for charity since.
Homes in Eastport
You will find Victorian-era houses, frame cottages, townhomes and condos, plus some newer construction. Several homes sit right on the water, and many streets end at it. Eastport is small, so homes do not come up often.
Why call us about Eastport
Jen Holden is a sailor and a member of the Eastport Yacht Club. Jane Holtz lives in Eastport. Megan Koppe grew up in nearby Bay Ridge and worked at Carrol’s Creek. Between us, we know the streets, the marinas and the flood questions that come with living on the water.
Thinking about a move to Eastport from Shipley’s Choice, Severna Park or somewhere else? Call Jen at 443.803.7620 or fill out the form on this page, and we will talk through what you want.
Eastport, Annapolis
Eastport Real Estate: Living on the Water in Annapolis
Eastport sits across Spa Creek from downtown Annapolis, with Back Creek on one side and the Severn River on the other. You can walk to dinner, watch sailboat races from a restaurant deck, and be at the State House by crossing the Spa Creek Bridge.
We know it well because our clients keep choosing it. Many sell a home in Shipley's Choice or Severna Park and move to Eastport for what comes next. Others are Naval Academy graduates or longtime locals who have wanted to come back for years.
1868
year the Eastport district was officially founded
1951
year Eastport was annexed into the City of Annapolis
1998
year residents declared the Maritime Republic of Eastport
$500K+
raised for charity by the Maritime Republic of Eastport
Moving from Shipley's Choice or Severna Park
Downsizing to Eastport.
We hear the same story often from sellers in Shipley's Choice and Severna Park. The house is bigger than they need now, the yard takes the whole weekend, and they want to be closer to the water without leaving Anne Arundel County.
Eastport is where many of them land. It is a real change, not a straight swap, so here is what we walk through before anyone lists or tours.
Shipley's Choice and Severna Park
Eastport
Space
More square footage and a bigger yard to care for.
Smaller homes on smaller lots, and many narrow streets.
Getting around
Most errands by car.
Restaurants, street-end parks and the water are close. Downtown Annapolis is across the Spa Creek Bridge.
The water
Access depends on the community and the street.
Water at the end of many streets, plus marinas, two creeks and the Severn River.
Parking
Driveways and garages are common.
Often tight. Look closely at parking for every home you tour.
Home styles
Colonials, split-levels and other suburban styles.
Bungalows, frame cottages, Victorian-era homes, townhomes, condos and some newer construction.
What gets easier
Less yard and exterior to maintain, depending on the home. Dinner, coffee and the water within walking distance. A smaller footprint to clean, heat and furnish.
What to look at closely
Stairs, since many older homes have steep ones, so ask where the bedroom and laundry are. Storage, because closets and basements are often smaller. Parking. And flood risk, which we cover below.
Timing the move
The hard part is usually the order: sell first, buy first, or do both at once. We plan the sale of your current home and your Eastport purchase together, so you know your options before anything is listed.
Curious what your current home could bring? See our recent results in Shipley's Choice and Greater Severna Park, or call Jen at 443.803.7620.
Water access and boating
You don't need a dock to live on the water here.
Eastport has water on three sides, and how close you live to it changes what you can do with it. Most buyers fall into one of three groups.
Waterfront with a dock
Your boat is at your back door. Ask about water depth at low tide, the size of boat the dock will hold, the condition of the bulkhead and piers, and whether the dock is permitted.
Water view, no dock
You get the view of Spa Creek, Back Creek or the Severn without a dock to maintain. Many owners rent a slip at a nearby marina.
Near the water
Many Eastport streets end at the water, with small parks for launching a kayak or paddleboard and watching the boats. The Annapolis Maritime Museum & Park on Back Creek has a beach and piers.
Sailing is part of the week.
The neighborhood has its own yacht club and several marinas. From the third week of April through the first Wednesday in September, sailboats race on Wednesday evenings starting at 6:00 p.m., run by the Annapolis Yacht Club. The restaurants along the water are a good place to watch.
If you boat, we can tell you which marinas and docks suit your boat before you fall for a house.
Flood and insurance, plainly
What to check before you write an offer.
Parts of Eastport sit low, and any waterfront neighborhood deserves a straight conversation about flooding. A 2011 study by the state and the City of Annapolis found the lowest ground along the Spa Creek and Back Creek shorelines and higher ground along the Severn. The study is old, so treat it as background, not as a verdict on any one home.
For any home you are serious about:
- Look up the address on the FEMA flood map.
- Ask the seller for an elevation certificate, if one exists.
- Get a flood insurance quote before your inspection period ends, not after.
We help buyers and sellers do all three early, so nothing surprises anyone at the closing table.
Everyday Eastport
Where Eastport eats, and where to watch the water.
Most of Eastport's restaurants sit within a few blocks of each other, so a night out is a walk, not a drive. You can reach downtown on foot over the Spa Creek Bridge or by water taxi.
Blackwall Hitch
Rooftop deck, an oyster and wine bar, and live music.
Boatyard Bar & Grill
Sailing-themed, with breakfast, a long bar and a dog-friendly deck.
Bread & Butter Kitchen
A neighborhood cafe on Second Street serving breakfast and lunch.
Carrol's Creek
Deck dining with a view of the Naval Academy.
Chart House
A water-view bar on the site of a former boatyard.
Davis' Pub
An old neighborhood pub known for crab balls and steamed shrimp.
Lewnes' Steakhouse
A family-owned steakhouse, open for dinner.
Oscar's Coffee Truck
Coffee at Horn Point Harbor Marina.
Menus and hours change, so check before you go.
History and traditions
A working waterfront with a sense of humor.
Eastport was farmland first, then a neighborhood of boatyards and oyster houses. Many early residents were watermen, boatwrights and craftspeople. The Eastport district was officially founded in 1868, and the City of Annapolis annexed it in 1951.
In January 1998, after the Spa Creek drawbridge was temporarily closed, residents declared Eastport the Maritime Republic of Eastport. The motto is "We like it this way." It started as a joke, and it never really stopped.
Every November, Eastport and downtown Annapolis pull against each other in the Tug of War, with a rope stretched across Spa Creek. It usually starts at noon, with parties on both shores. The Maritime Republic is a registered nonprofit and has raised more than $500,000 for charity. Other traditions include an annual bridge run and the spring Burning of the Socks.
Eastport's oldest house.
A marker on Eastport's walking tour points out the Williams House, the oldest house in the neighborhood. Jonas and Louisa Williams moved in with their eight children in 1876 and ran a grocery on the first floor. It stayed in the family until 1972, and it is a bed and breakfast today.
Eastport is also home to one of the oldest African American communities in the country, including Mt. Zion United Methodist Church, founded in 1896 on Second Street, and the Peerless Rens Club.
That history is part of why homes here rarely feel alike, and why it helps to walk them with someone who knows the streets.
For people who already know Annapolis
Coming back to Eastport.
A lot of our Eastport buyers have a history here. Some graduated from the Naval Academy and kept Annapolis in the back of their minds through years of moves. Others grew up in the area and always planned to return.
When you have known a place for years, the questions get specific. What has changed? Which streets sit lower? What is parking like on a Friday night? We answer those plainly, then show you homes that fit what you remember and what you need now.
Your Eastport neighbor
Meet Jane Holtz.
Jane lives in Eastport with her husband, Allan. Allan sails in the Friday night Beer Can races at the Eastport Yacht Club. You will often find Jane playing pickleball at Safe Harbor, at an Annapolis Garden Club meeting, or getting coffee at Oscar's.
She also shows up for the neighborhood. This summer she hosted a back-to-school ice cream social on Sunday, August 30, at Horn Point Harbor Marina on Eastern Avenue, with Always Ice Cream and Oscar's open for the afternoon. The event included a school supply drive for Eastport Elementary and a raffle for Always and Oscar's gift cards. Marie Ritzenberg of Origin Point sponsored it.
Jane helps Eastport homeowners understand the market, work out what their home could sell for, and plan ahead when a move may be coming. She also works with buyers hoping to make Eastport home. Call even if moving is still a long way off. Reach her at 443.472.0092 or jane.holtz@compass.com.
The whole team works here
Who you work with matters.
Jen, Megan and Jane all work with clients in Eastport, and each one has a personal tie to the neighborhood.
Jen Holden
Realtor® | Principal
A member of the Eastport Yacht Club and an active sailor. She races on Wednesday nights, sails regattas and is part of the EYC Book Club. She also plans the sale and the purchase together for clients leaving Shipley's Choice and Severna Park.
Megan Koppe
Realtor® | Senior Agent
Megan grew up down the road in Bay Ridge and worked at Carrol's Creek while she was growing up. She has more than a decade of experience helping buyers and sellers across Anne Arundel County, including Eastport.
Jane Holtz
Realtor®
Lives in Eastport and helps local homeowners plan ahead and buyers make Eastport home. A lifelong Marylander with more than 30 years in consultative sales, Jane holds the Accredited Buyer's Representative (ABR®) and Seniors Real Estate Specialist (SRES®) designations and is military relocation certified.
$41.9M
in sales volume for The Jen Holden Group in 2025
54
transactions for our clients in 2025
Common questions
Eastport, answered.
Is Eastport a good place to downsize from Severna Park or Shipley's Choice?
For many people, yes. You trade square footage and yard for walkability and the water. It works best when you have seen the tradeoffs first: stairs, parking, storage and flood risk. We walk through those on every tour.
Do I need a waterfront home to boat from Eastport?
No. Many owners rent a slip at a nearby marina, and several streets end at the water with places to launch a kayak or paddleboard. A waterfront home with a dock is one option, not the only one.
Is flood insurance required in Eastport?
It depends on the property, its FEMA flood zone and your lender. If a home is in a high-risk flood zone and you have a mortgage, your lender will require it. Either way, we suggest getting a quote before you commit.
What kinds of homes are in Eastport?
A mix of bungalows, frame cottages and Victorian-era homes, plus townhomes, condos and some newer construction. Lots are small and many streets are narrow.
Is Eastport part of Annapolis?
Yes. The City of Annapolis annexed Eastport in 1951, and it is in Anne Arundel County. Plenty of residents still call it the Maritime Republic.
How do I get downtown from Eastport?
On foot or by bike over the Spa Creek Bridge, by car, or by water taxi.
Sources: Annapolis Home, "Neighborhood Visit: The Maritime Republic of Eastport" (annapolishomemag.com); Chesapeake Bay Program, "Public art tells the story of a community" (chesapeakebay.net); Wikipedia, Maritime Republic of Eastport; VisitAnnapolis, Eastport, Exploring Eastport's Eateries and The MRE Tug of War; Waterway Guide, Eastport, MD; Maryland DNR and City of Annapolis, Eastport flood mitigation study (2011); Eastport walking tour marker for the Williams House. Restaurant and event details can change. Flood information is general background, not a flood determination for any property. Check current FEMA maps and get an insurance quote for any home you are considering.
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Jane Holtz
jane.holtz@compass.com