By Adam Chubbuck, Team Leader, Team Alpha Charlie of Douglas Realty. Retired U.S. Navy Chief. Licensed in Maryland and Virginia.
Annapolis is a small city that behaves like a dozen different housing markets. A brick townhouse on a colonial street, a bungalow across the creek with a boat in the backyard, a mid-century rancher on a half acre, and a waterfront estate on the Severn are all Annapolis addresses, and they have almost nothing in common as purchases.
Buyers who search “Annapolis homes for sale” and sort by price learn this the hard way. So here is the neighborhood level breakdown, what each one is actually like, and the two things about buying in this city that catch people off guard.
The Market Context
Zillow put the average Annapolis home value at $633,333 as of June 30, 2026, up 2.0 percent year over year, with homes going to pending in around 10 days. A February 2026 analysis projected a median around $675,000 with homes averaging about 30 days to sell.
For county context, Maryland REALTORS reported an Anne Arundel County median sale price of $535,000 with an 8 day median time to contract for June 2026. Annapolis carries a meaningful premium over the county, and within Annapolis the spread between neighborhoods is wider still.
Inside the City Walls: The Historic District
Best for: buyers who want to walk out the door into the most intact colonial city in America and are willing to accept the constraints that come with it.
This is the reason people fall in love with Annapolis. Brick sidewalks, eighteenth century architecture, State Circle and Church Circle, City Dock, and a downtown you can genuinely live in without a car. The Naval Academy sits at the edge of it. There is nothing else like it on the East Coast.
What you are buying. Rowhouses and detached historic homes, many dating to the eighteenth and nineteenth centuries. Small lots or no lot at all. Character in every direction.
The constraints, and they are real.
Historic district properties carry stricter renovation rules. Exterior changes are typically subject to review, which affects windows, siding, roofing materials, paint in some cases, and additions. Buyers who plan to gut and modernize should understand the approval process before they close, not after.
Parking is a genuine issue and it is not a minor one. Some properties have dedicated parking and many do not. If you own two cars, verify what you actually get.
Older housing stock means older systems. Knob and tube remnants, plaster, original windows, foundations that predate modern construction. Inspect thoroughly and budget accordingly.
Flooding. Portions of downtown near City Dock experience nuisance flooding, and it has become more frequent. Pull the flood zone determination and get an actual insurance quote rather than an estimate.
Eastport
Best for: buyers who want the sailing culture and a genuine neighborhood identity without downtown’s constraints.
Across Spa Creek from downtown, Eastport is its own thing and proud of it. Working maritime businesses, boatyards, marinas, a strong local restaurant and bar scene along Fourth Street, and a resident culture with an actual sense of humor about itself.
What you are buying. A mix of modest bungalows, cottages, renovated older homes, and waterfront property on Spa Creek and Back Creek. The range within Eastport is wide.
Why buyers like it. You are a walk or a short water taxi ride from downtown, you are in the middle of the Chesapeake sailing world, and the neighborhood has a community feel that the Historic District, with its tourist volume, does not.
The tradeoffs. Prices have risen substantially. Some of the housing stock is small by modern standards. And like anywhere in Annapolis near the water, verify flood zone and elevation.
Murray Hill
Best for: buyers who want walkability to downtown with a residential neighborhood feel and slightly more house.
Just west of the Historic District, Murray Hill is one of the most consistently desirable addresses in the city. Tree lined streets, early twentieth century homes with real architectural character, and a five to ten minute walk to State Circle.
You get downtown access without downtown’s parking situation or the full weight of historic district review, though portions may still fall within review areas depending on the specific property. Verify.
The tradeoff. It is expensive and inventory is limited. Murray Hill homes do not come up often and they do not sit.
West Annapolis
Best for: buyers who want a walkable village center and a more conventional residential experience.
Across Weems Creek from the Historic District, West Annapolis has its own small commercial strip along Annapolis Street with restaurants, shops, and a genuine neighborhood center. Housing runs to bungalows and cottages, generally more modest than Murray Hill.
Why it works. You get walkability and character at a lower entry point than downtown or Murray Hill, with quick access to Route 50 and the rest of the county.
Wardour, Presidents Hill, and Admiral Heights
The established residential neighborhoods ringing the historic core.
Wardour sits on the Severn River side with substantial homes, mature landscaping, and water access. It is one of the premium residential addresses in the city.
Presidents Hill is a small, walkable enclave adjacent to Murray Hill with strong character and limited inventory.
Admiral Heights offers more conventional mid-century housing on real lots with a community pier arrangement, and it is one of the better values for buyers who want water access and proximity to downtown without historic district pricing or constraints.
Annapolis Neck: Hillsmere, Bay Ridge, Annapolis Roads, and Fishing Creek Farm
South of downtown down Bay Ridge Avenue and Forest Drive, the Annapolis Neck peninsula holds a substantial share of the area’s water oriented residential inventory.
Hillsmere Shores is a large community with a beach, marina, and pool, offering community water access at prices well below true waterfront. It is one of the most practical water access values in the immediate Annapolis area.
Bay Ridge occupies the tip of the peninsula with Chesapeake Bay frontage and views, a beach, and a strong community structure. Premium pricing and genuinely spectacular water.
Annapolis Roads offers Bay access, a golf course, and an established residential character.
Fishing Creek Farm and similar communities offer newer, larger homes on the water side of Forest Drive.
The Forest Drive caution. Traffic on Forest Drive is a real quality of life factor and it is worth experiencing before you buy. At rush hour, getting from the Neck to Route 50 takes longer than the mileage suggests.
The Severn River Communities
Epping Forest and Sherwood Forest are private communities on the Severn with their own governance, amenities, and character. Sherwood Forest in particular operates on a distinctive model that buyers should understand thoroughly before pursuing. These are not conventional subdivisions and the purchase process differs.
Winchester on the Severn and the surrounding Severn River communities offer water access and a quieter setting with a slightly longer run to downtown.
Heritage Harbour and the 55+ Option
Heritage Harbour off Riva Road is the area’s best known active adult community, with substantial amenities, a golf course, and a clubhouse. For downsizing buyers who want to stay in Annapolis, it is the primary answer, and it trades on its own dynamics rather than the general market.
The Two Things That Catch Annapolis Buyers Off Guard
One: City property taxes are on top of county taxes
This is the one out of county buyers miss.
Anne Arundel County publishes separate tax information for the City of Annapolis and the Town of Highland Beach precisely because their rate structures differ from the general county rate. For the tax period July 1, 2026 through June 30, 2027, the county real property rate is $0.968 per $100 of taxable assessment and the state rate is $0.112 per $100. Municipal properties carry their own additional structure.
There is a second, more consequential difference. Anne Arundel County sets its Homestead Tax Credit cap, which limits how much your taxable assessment can rise each year on a principal residence, at 2 percent. The City of Annapolis sets its limit at 10 percent, which applies to taxes levied by the City.
That is a real long term difference in how fast your tax bill can grow after a reassessment. It is not a reason to avoid the city, but it belongs in your math, and almost nobody explains it to buyers. Verify current rates and structures directly with Anne Arundel County and the City of Annapolis, and remember you must apply for the Homestead Credit, with applications due December 31 to take effect the following July 1.
Two: The Chesapeake Bay Critical Area applies throughout
Annapolis is surrounded by tidal water. The Critical Area covers all land within 1,000 feet of the mean high water line of tidal waters, which means a substantial share of city property, including plenty of homes that are not on the water.
That brings a minimum 100 foot buffer, impervious surface limits, forest clearing restrictions, and lot coverage rules that count more surfaces than buyers expect, including gravel, pavers, and permeable pavement. If you plan to add on, build a deck, put in a pool, or clear trees for a view, verify feasibility with Anne Arundel County Planning and Zoning at 410-222-7463 before you close. I cover the Critical Area in full in a separate article.
Choosing Between Them
- Maximum walkability and historic character: Historic District, then Murray Hill.
- Sailing culture and neighborhood identity: Eastport.
- Walkable village at a lower entry point: West Annapolis.
- Water access without waterfront pricing: Hillsmere Shores, Admiral Heights.
- Premium waterfront: Bay Ridge, Wardour, the Severn River communities.
- Space and value with downtown proximity: Admiral Heights, or step outside the city to Arnold.
- Downsizing in place: Heritage Harbour.
And the comparison worth running: Arnold and Crofton offer more square footage, larger yards, and strong schools at a lower cost per square foot than the city. If walkability is not your top priority, look at Arnold before you commit to an Annapolis premium you may not use. I cover Arnold and the Broadneck peninsula in a separate guide.
Working This Market
Annapolis rewards local knowledge more than almost any market I work, because the variables that drive value here, historic review status, flood exposure, parking, Critical Area constraints, what a community water access right actually conveys, and which side of the city tax line an address falls on, are invisible in listing photos and absent from automated valuations.
I have closed more than 350 homes across this corridor over the past five years, and I run Enclave Property Management out of Pasadena, so I see Annapolis property from the ownership side as well as the transaction side.
If you are considering Annapolis, or trying to decide between the city and the surrounding county, reach out to Team Alpha Charlie of Douglas Realty. If you are earlier in the process, the free Anne Arundel County home valuation and my breakdown of current Anne Arundel County home prices by submarket are useful starting points. For Naval Academy and NSA Annapolis families, Maryland BAH rates heading into 2027 shapes what is actually reachable here.
Annapolis Neighborhoods FAQ
What is the best neighborhood in Annapolis?
It depends on priority. For historic character and maximum walkability, the Historic District. For sailing culture and neighborhood identity, Eastport. For walkable residential character with slightly more house, Murray Hill. For water access at a more accessible price, Hillsmere Shores or Admiral Heights. For premium waterfront, Bay Ridge or Wardour.
How much do homes cost in Annapolis, MD?
Zillow put the average Annapolis home value at $633,333 as of June 30, 2026, up 2.0 percent year over year, with homes going pending in around 10 days. A February 2026 analysis projected a median around $675,000. The range between neighborhoods is very wide, from modest Eastport cottages to multi-million dollar Severn River and Bay waterfront.
Are there restrictions on renovating a home in the Annapolis Historic District?
Yes. Historic district properties carry stricter renovation rules, with exterior changes typically subject to review affecting windows, siding, roofing materials, and additions. If you plan significant exterior work, understand the review process before you close. Verify the specific requirements for any address, since review boundaries and standards are property specific.
Is Annapolis or Arnold better for families?
Annapolis offers walkability, history, and downtown life at a premium. Arnold offers more square footage, larger yards, and Broadneck High School, which holds a Niche grade of A, at a lower cost per square foot, roughly ten minutes from downtown Annapolis. If walkability is not your top priority, Arnold typically delivers more house for the money.
Do Annapolis city residents pay higher property taxes?
City of Annapolis properties carry a municipal tax structure separate from the general county rate, which for the period July 1, 2026 through June 30, 2027 is $0.968 per $100 county plus $0.112 per $100 state. A more consequential long term difference: Anne Arundel County caps annual Homestead assessment increases at 2 percent while the City of Annapolis sets its limit at 10 percent for City-levied taxes. Verify current rates with the county and the City directly.
Does the Chesapeake Bay Critical Area affect Annapolis properties?
Substantially. The Critical Area covers all land within 1,000 feet of the mean high water line of tidal waters, which includes a large share of Annapolis property, not only waterfront. Expect a minimum 100 foot buffer, impervious surface limits, and forest clearing restrictions. Verify with Anne Arundel County Planning and Zoning at 410-222-7463 before making renovation plans.
Sources and Dates
Annapolis home value figures reflect Zillow Home Value Index updated June 30, 2026, and a market analysis published February 2026. Anne Arundel County median sale price and time to contract reflect Maryland REALTORS Housing Statistics, June 2026. Property tax rates, Homestead Tax Credit cap figures for Anne Arundel County and the City of Annapolis, and the separate municipal tax information structure are drawn from Anne Arundel County Government published FY27 Property Tax Bill Information for the period July 1, 2026 through June 30, 2027. Critical Area requirements reflect Anne Arundel County Planning and Zoning published guidance. Broadneck High School rating reflects Niche 2026. All market figures change and describe aggregates rather than specific properties. Historic district review requirements, flood zone status, parking, Critical Area classification, and tax treatment must be verified independently for any specific address. This article is general information and not legal, tax, or land use advice.
Let’s Talk About Your Move
If Annapolis is on your list, the fastest way to make progress is narrowing which version of Annapolis you actually want. Tell me whether you want to walk to dinner or park a boat, and what your budget is, and I will show you the two or three neighborhoods that fit and the real comps in each.
I am Adam Chubbuck, Team Leader of Team Alpha Charlie of Douglas Realty. I am a retired U.S. Navy Chief, a licensed Real Estate agent in Maryland and Virginia, and I have closed more than 350 homes over the past five years across the Baltimore to Annapolis corridor. My team serves buyers and sellers throughout Anne Arundel County, Howard County, Baltimore County, Baltimore City, and the surrounding markets, with deep experience supporting military, veteran, and Department of Defense families. I also run Enclave Property Management out of Pasadena, Maryland, so I see this market from the ownership side as well as the sales side.
If you are weighing a move, start with a real conversation and real numbers. Reach me directly at 443-347-6692, email [email protected], or start at TACMD.com.
Adam Chubbuck
Team Leader, Team Alpha Charlie of Douglas Realty
Douglas Realty | Licensed in MD and VA
443-347-6692 | [email protected] | TACMD.com
Smile more,
Adam Chubbuck
