Three houses sold in Eastport within the last ten months. One went for $589 a square foot. One went for $658 a square foot. One went for $2,018 a square foot. All three carry the same neighborhood name on the listing sheet. None of them are competing for the same buyer.
The first, a two-bedroom condo at 100 Severn Ave, built in 1976, sold in March 2026 after 17 days on market, 6 percent below its list price. The second, a colonial at 600 Sixth St, built in 1935, sold in November 2025 for $2.2 million after 13 days on market. The third, a 2,949-square-foot unit at 287 State St, built in 2022, sold in April 2026 for $5.95 million with zero days on market. It never really hit the open market at all.
If you are comparing Eastport to another Annapolis neighborhood, or comparing two Eastport listings to each other, the median price you find on a portal search is quietly averaging these three very different transactions into one number. That number is real. It is also not describing one market. It is describing two.
Two Boatyards Made This Possible
The reason Eastport can produce a $2,018-a-square-foot sale and a $589-a-square-foot sale in the same season traces back to a specific piece of waterfront on Spa Creek. For most of the last century, the site now known as the South Annapolis Yacht Centre operated as Sarles Boatyard, founded in 1907, and later Petrini Shipyard, founded in 1946, making it among the oldest continuously operating marine facilities in the Annapolis area. Under new ownership, the property was redeveloped into a boutique enclave of eleven new waterfront residences replacing the eleven older structures that previously sat on the site.
That redevelopment is what put a 2022-built, $2,018-a-square-foot condo inside the same zip code as a 1935 colonial and a 1976 mid-rise. Eastport itself dates to 1910, and most of its original housing stock still reflects that era: 1920s Craftsman cottages, Cape Cods, and colonial-style houses built for boatyard workers and watermen, not for buyers pricing waterfront square footage against a marina view. The neighborhood didn't get more expensive uniformly. A narrow slice of it got rebuilt from the ground up, and that slice now sells at a price per square foot that has almost nothing to do with the rest of the peninsula.
This is the mechanism a single median price can't show you. It isn't that Eastport appreciated. It's that two different products, built eighty-some years apart, are now transacting under one neighborhood label.
What the Citywide Median Is Also Hiding
The same pattern shows up at the city level, and it produces a number that looks contradictory until you know what's driving it. Over the three months ending May 2026, Annapolis's median sale price was $597,000, down 12.8 percent from the same period a year earlier. In that same window, the median sale price per square foot was $444, up 27.6 percent year over year.
A falling median next to a rising price per square foot is not a market getting cheaper and more expensive at the same time. It's a signal that the mix of what sold changed. When smaller, higher-cost-per-square-foot properties, think renovated cottages and downtown condos, make up a larger share of a given quarter's closings than large suburban houses do, the median sale price can drop even while buyers are paying more for every square foot they get. Fewer big houses closed, more small, expensive-per-foot ones did, and the blended median moved in the opposite direction of the actual cost of housing.
An earlier read on the same city, from January 2026, reported price per square foot up 18.3 percent year over year, among the strongest gains anywhere in Anne Arundel County. That same snapshot broke Annapolis into its component neighborhoods, and the spread is the clearest evidence that "the median" is really several medians stacked on top of each other:
| Sub-market (Jan. 2026 single-family median) | Price |
|---|---|
| Downtown Historic District | $1,447,500 |
| Eastport | $1,102,500 |
| West Annapolis / Wardour | $790,000 |
| Citywide (all property types) | $615,000 |
Downtown Historic pulls its median up through scarcity and preservation status. Eastport pulls its up through the same boatyard-to-marina-village conversion that produced the $2,018-a-square-foot sale. West Annapolis and Wardour, with more conventional suburban lots, sit meaningfully below both. Blend all of it with the citywide condo and townhome inventory, condos in the $343,000 to $399,000 range depending on bedroom count, and you get a single figure that describes none of the underlying neighborhoods particularly well.
What This Means If You're Comparing Two Listings
If you're using price per square foot as your shorthand for value in Eastport, the year a building went up matters as much as its address. A 2022 waterfront condo and a 1935 colonial two streets over are not offering variations on the same product. One is trading on new construction, marina proximity, and a redevelopment story tied to a specific site. The other is trading on lot size, character, and whatever updates its owners made along the way.
Before treating two Eastport comps as equivalent, it's worth asking a short set of questions:
- What decade was this specific structure built, not just the neighborhood founded?
- Is the price per square foot closer to the $589 to $658 range of the neighborhood's older housing stock, or closer to the $2,000-plus range tied to new waterfront construction?
- How many days did it actually spend on the open market? A sale that closed with zero days on market, like 287 State St, usually means it moved through a pre-marketing or off-market channel built for that specific product type, not the same buyer pool competing for a renovated cottage.
- Does the listing sit within walking distance of Eastport's original commercial core, near Horn Point Park, the Eastport Shopping Center, or longtime local spots like The Boatyard and Davis' Pub, or is it positioned around a newer waterfront development?
None of this means one part of Eastport is a better buy than another. It means the two parts answer different questions, and a single median price was never built to answer either one precisely.
A Few Questions Worth Asking Before You Compare
Does new construction near the water pull older Eastport home values up with it? The data available doesn't isolate that effect cleanly. What it does show is that the two segments currently sell at very different prices per square foot, which suggests they aren't yet functioning as close substitutes in buyers' minds. Older homes are being valued on their own terms, not simply chasing the new-construction number upward.
Is Annapolis's falling median sale price a sign the market is softening? Not on its own. A median that drops while price per square foot rises in the same window is more consistent with a change in what happened to sell that quarter than with a broad decline in value. Any specific property still needs its own comparables, not the citywide headline number.
Why did one Eastport sale close with zero days on market? New, limited-inventory developments like the South Annapolis Yacht Centre residences often move through relationships and pre-marketing before they're widely listed, which is common for boutique waterfront projects with a small unit count.
If you're weighing a purchase or a sale anywhere between a century-old Eastport cottage and a new waterfront build, the number that matters isn't the neighborhood median. It's the comparable that actually matches the property in front of you, in age, location, and construction era. Jeannine Wayson has spent more than two decades pricing Annapolis and Eastport property against exactly that kind of detail. Let's Connect — Schedule a Free Consultation.
