Boating in Maryland: the Chesapeake, Its Rivers, and the Ocean City Inlet
Of the roughly 200 boats and yachts for sale by owner in Maryland on YachtBazar today, the
median asking price is $28,000. Sailboats are the second-largest type behind
general powerboats — ahead of
fishing boats and cruisers/motor yachts by title keyword — and two of the four most-listed makes in
the state, Hunter and Beneteau, are sailboat builders. That skew is exactly what the geography
predicts: Maryland boating centers on the Chesapeake Bay, the largest estuary in the United
States — protected water, tidal rivers and steady summer breeze — and Annapolis, which has
styled itself "America's Sailing Capital" for decades, carries more listings than any other
city in the state.
The Bay reads differently by stretch. The upper Bay around Baltimore and Middle River is
river-mouth water — the Patapsco, Back and Middle rivers — with city marinas a short run from
open water. Between Baltimore and Annapolis, river towns like Pasadena and Severna Park line
the necks of the Magothy and Severn; all five of Maryland's top listing cities sit on this
western shore. Across the Bay Bridge, the Eastern Shore — Kent Island, Kent Narrows, the
Choptank — is shallower, quieter cruising and crabbing water. And Maryland has an ocean side
too: the Atlantic inlet at Ocean City is the state's offshore-fishing port, running a
different fleet — center consoles and sportfish — than the sloops and cruisers of the Bay.
Annapolis, Pasadena, Middle River, Baltimore and Severna Park carry the most listings
statewide, with asking prices from $5,000 to $798,000 across 12 to 70 ft of boat. See the
by-owner sailboats for sale in Maryland,
boats priced $25,000 to $50,000 in
Maryland — the band the state's median asking price falls into — or
Maryland boat slips & docks if you need somewhere on
the Bay to keep what you buy.
$139,0002001Formula 41PC Boat📍 Fredericktown, MD
$1,395,0002023 Prestige Yachts 590 Fly📍 Baltimore, MD
$139,0002023 Chaparral 267 SSX Boat FOR SALE📍 Annapolis, MD
$69,9002017 Sea Ray SDX 270📍 Annapolis, MD
$75,0002022 Sailfish 220📍 Elkton, MD
$110,0002025 Monterey 255 super sport📍 Dundalk, MD
$179,9002027 Pioneer Boats 270 pelagic📍 Annapolis, MD
$110,000Sea Ray Sundancer 340📍 Edgewater, MD
$149,0001948 Chris Craft 25’ Sportsman📍 Severna Park, MD
$173,1332026 Monterey Boats Elite 25📍 Annapolis, MD
$60,0001988 Sea Ray 430 Convertible | 43ft Boat📍 Joppa, MD
$159,0002015 Concept 36 Cuddy📍 Sparrows Point, MD
$69,9901985 Bertram 38 Convertible📍 Essex, MD
$84,9002004 Regal commodore 3860📍 Annapolis, MD
$125,0002006 Four Winns 378 vista (diesel)📍 Chestertown, MD
$80,0002010 Seahunt gamefish 26📍 Halethorpe, MD
$79,9002006 Boston Whaler 305 Conquest📍 Severna Park, MD
$55,0001997 Wellcraft 330 Coastal📍 Parkville, MD
$78,00027 ft sailfish center console📍 Silver Spring, MD
$198,4952020 Aviara AV32 OB📍 Galena, MD
$64,0002002 Chaparral signature 350📍 Havre de Grace, MD
$175,0002002 SeaRay 410 Express📍 Essex, MD
$100,0001989 Carver 4207📍 Middle River, MD
$51,9002015 Tidewayer 230 CC Adventure📍 Annapolis, MD