Trawlers For Sale in Chesapeake Bay

19
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median sold price
$114,500
sales on record
194
years built
1938–2023
typical length
22–54 ft
for sale now
19
Nordic Tugs 34
New Arrival! (Oct 14, 2026)

Nordic Tugs 34 (Chesapeake Bay)

Price $319,500 (USD)
Location Woodbridge, Virginia (Chesapeake Bay)
M/Y Sterling — a 2015 Nordic Tugs 34, for sale by broker.
Sterling is a 2015 34′ Nordic Tugs raised pilothouse trawler. She offers a low-hour Volvo-Penta 260 HP main engine, low-hour Northern Lights 5 kW generator, Side-Power bowthruster, oil change system, new Victron Energy 2,000 watt inverter/charger, two new 320 watt Renogy solar panels with a new Victron Energy controller, new and upgraded Victron Energy 480 a-H AGM house battery bank, new Victron Energy communication center/control hub, galvanic isolator, Trac Ecological Seaflush winterization/descaling system, Portland Pudgy tender with a Suzuki 2.5 HP outboard and a clean, uncluttered interior.…
72 Photos
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Monk 36 Double Cabin
Updated! (Oct 12, 2026)

Monk 36 Double Cabin (Chesapeake Bay)

Price $79,500 (USD)
Location Shady Side, Maryland (Chesapeake Bay)
M/Y Dragonfly — a 1988 Monk 36 Double Cabin, for sale by broker.
Dragonfly is a 1988 36′ Monk double cabin trawler. She offers a single Perkins 135 HP main engine, NextGen 8 kW generator, Vetus bowthruster, reverse cycle air conditioning/heating system, 2024 aluminum fuel tanks, solar panels, AIS and a 2 stateroom 2 head layout. Dragonfly has an attainable 13′ height with the mast and bimini lowered and she is a Great Loop veteran.…
76 Photos
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Custom Marquis 55LS

Custom Marquis 55LS (Chesapeake Bay)

Price $549,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Sunline — a 2007 Custom Marquis 55LS, for sale by broker.
Meet SUNLINE, a 2007 Marquis 55 LS that has been transformed through an extensive series of mechanical, interior and exterior upgrades. With three staterooms, a full-beam master suite , SUNLINE delivers the space and amenities expected of a much larger motor yacht while maintaining a comfortable, highly functional layout for cruising and entertaining. The enclosed, climate-controlled flybridge is a standout feature, offering panoramic visibility along with a wet bar, electric grill, ice maker and refrigerator. Below, the main-deck salon and galley have been refreshed with new hardwood flooring, granite countertops, updated cabinetry, new appliances, sinks and faucets, new window treatments and wood-trimmed walls and ceilings.…
37 Photos
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Grand Banks 42 Classic

Grand Banks 42 Classic (Chesapeake Bay)

Price $124,500 (USD)
Location St. Michaels, Maryland (Chesapeake Bay)
M/Y Maia — a 1989 Grand Banks 42 Classic, for sale by broker.
Maia is a 1989 42′ Grand Banks Classic model. She offers twin Cummins 250 HP main engines, a Northern Lights 8 kW generator, an oil change system, a 2023 West Marine RIB tender with a Yamaha 6 HP four-stroke outboard, a flybridge bimini and Eisenglass enclosure, and a classic Grand Banks interior. Maia is Great Loop capable with her attainable 13’1″ height above the waterline to the flybridge windscreen and 16′ height to the top of the bimini.…
85 Photos
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Hatteras 54

Hatteras 54 (Chesapeake Bay)

Price $245,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)
M/Y Material Girl — a 1987 Hatteras 54, for sale by broker.
Material Girl is a 1987 54′ Hatteras motoryacht. She offers twin Detroit Diesel 735 hp main engines (overhauled in 2011) (compression test in 2019 showed 485–490 psi on all cylinders), an Onan 20 kW generator, a Xantrex 1,000-watt inverter, a Dickson stern thruster, Naiad stabilizers, a climate-controlled aft deck, and a three-stateroom, three-head layout. With the equipment on top of the radar arch removed, Material Girl is Great Loop capable.…
100 Photos
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Defever 49 CPMY

Defever 49 CPMY (Chesapeake Bay)

Price $425,000 (USD)
Location Smithfield, Virginia (Chesapeake Bay)
M/Y Sea Cow — a 2004 Defever CPMY, for sale by broker.
Sea Cow is a 2005 49′ DeFever CPMY (know as 44+5 model as it added 5′ to the very popular 44′ model). She is ready to cast off lines and travel . She was on her second Great Loop until owner health issues makes her available. This popular sundeck layout offers aft full-beam master stateroom, large flybridge and a spacious cockpit. Fully outfitted for extended cursing including Twin Perkins Saber 135 HP main engines, stand up engine room, two westerbeke generators, Naida stabilizers, bow thruster, Flo Scan fuel monitoring, FIC fuel purifier, oil change system, watermaker, Starlink, AIS (send/receive), and Bosch washer and dryer.…
95 Photos
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Sea Ray 40
Updated! (Oct 13, 2026)

Sea Ray 40 (Chesapeake Bay)

Price $219,500 (USD)
Location Pasadena, Maryland (Chesapeake Bay)
M/Y Dawn Watch — a 2007 Sea Ray 40, for sale by broker.
Dawn Watch is a 2007 40′ Sea Ray motoryacht. She offers twin Cummins 425 HP main engines, an Onan 9 kW generator, an oil change system, a bow thruster, a climate-controlled sundeck and helm, and a two-stateroom, two-head layout. The full-beam master stateroom aft offers a separate head and shower. With her 15’6″ height above the waterline, she is a perfect Great Loop candidate.…
62 Photos
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Sabre 42 Flybridge

Sabre 42 Flybridge (Chesapeake Bay)

Price $375,000 (USD)
Location Chesapeake, Virginia (Chesapeake Bay)
M/Y Lucille — a 2006 Sabre 42 Flybridge, for sale by broker.
Lucille is a 2006 42′ Sabre flybridge model. She offers twin Yanmar 500 hp main engines, an Onan 11.5 kW generator, a Xantrex 3,000-watt inverter, a galvanic isolator, Side-Power bow and stern thrusters, an oil change system, a 2023 AB aluminum-hull tender, and a 2-stateroom layout. With her attainable 13’5″ height, Lucille is a strong Great Loop candidate.…
145 Photos
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Hatteras 48 LRC

Hatteras 48 LRC (Chesapeake Bay)

Price $199,500 (USD)
Location Poquoson, Virginia (Chesapeake Bay)
M/Y Overdraft — a 1976 Hatteras 48 LRC, for sale by broker.
Overdraft is a 1976 48′ Hatteras raised pilothouse Long Range Cruiser (LRC). She is Great Loop capable and a proven bluewater long range cruiser.…
99 Photos
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President 43

President 43 (Chesapeake Bay)

Price $62,000 (USD)
Location Baltimore, Maryland (Chesapeake Bay)
Valkomenn — a 1985 President 43, for sale by broker.
Valkomenn is a Great Loop–ready and Loop-proven motor yacht, making her an ideal choice for anyone seeking a turnkey trawler-style cruiser for long-distance adventures. Having successfully completed the Great Loop, she offers the reliability and real-world performance that serious cruisers value. This President 43 motor yacht has been thoughtfully upgraded with modern marine electronics, ensuring safe and efficient navigation whether you’re cruising inland waterways or coastal passages. With recent mechanical service and maintenance completed, she is fully prepared for extended cruising with minimal downtime.…
26 Photos
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Ocean Alexander 50 Mark II Pilothouse

Ocean Alexander 50 Mark II Pilothouse (Chesapeake Bay)

Price $119,000 (USD)
Location Suffolk, Virginia (Chesapeake Bay)
M/Y Surprise — a 1986 Ocean Alexander 50 Mark II Pilothouse, for sale by broker.
Price reduction — SURPRISE is a 1986 Ocean Alexander 50 Mark II, a pilothouse motor yacht known for its furniture-quality teak joinery, spacious tri-level layout, and seaworthy semi-displacement hull. It is an ideal vessel for liveaboards and long-distance cruisers on routes like the Great Loop. SURPRISE is in good condition and has been owned by the seller for 20 years. She has three staterooms, two full heads, a spacious galley, a roomy, attractive salon, and a pilothouse with great visibility and easy access to the side decks for docking.…
91 Photos
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Custom 65

Custom 65 (Chesapeake Bay)

Price $300,000 (USD)
Location Saint Michaels, Maryland (Chesapeake Bay)
M/Y Choptank — a 1938 Custom Chesapeake Bay Buyboat, for sale by broker.
Choptank is for sale! She is a 1938 65′ O.W. Payne–designed and built Chesapeake Bay Buyboat. Choptank underwent a major rebuild from 2011 to the present and has been maintained since by the Chesapeake Bay Maritime Museum’s experienced and knowledgeable local shipwrights. The museum stopped the rebuild at the point where she can be completed as a commercial vessel with a COI or as a pleasure vessel. You could hire the museum to complete the project or complete her elsewhere or by yourself to your final design and specs.…
66 Photos
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Ocean Alexander 450 Classico

Ocean Alexander 450 Classico (Chesapeake Bay)

Price $244,500 (USD)
Location Norfolk, Virginia (Chesapeake Bay)
M/Y It's About Time — a 2000 Ocean Alexander 450 Classico, for sale by broker.
It’s About Time is a 2000, 45′ Ocean Alexander 450 Classico sedan motoryacht. She is a Great Loop veteran.…
75 Photos
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Mainship 34 Pilot

Mainship 34 Pilot (Chesapeake Bay)

Price $99,500 (USD)
Location Tilghman, Maryland (Chesapeake Bay)
M/Y Ragtop Lady — a 2006 Mainship 34 Pilot, for sale by broker.
2006 34′ Mainship Pilot Express Cruiser Ragtop Lady is a 2006 34′ Mainship Pilot. She offers twin Yanmar 240 hp main engines, a Next Gen 5.5 kW generator, an oil change system, dripless shaft seals, a galvanic isolator, a reverse-cycle air conditioning and heating system, a Magnum inverter, and a full Eisenglass enclosure.…
50 Photos
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Kadey-Krogen 36 Manatee

Kadey-Krogen 36 Manatee (Chesapeake Bay)

Price $119,500 (USD)
Location Baltimore, Maryland (Chesapeake Bay)
M/Y Matty Beau — a 1985 Kadey-Krogen 36 Manatee, for sale by broker.
Matty Beau is a 1985 36′ Kadey-Krogen Manatee trawler. The boat was hauled and the bottom painted in Spring 2026. Matty Beau is Great Loop capable.…
60 Photos
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Post 46
$34,000 (USD) Price Drop! (Oct 7, 2026)

Post 46 (Chesapeake Bay)

Price $95,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)
M/Y Jubilee — a 1988 Post 46, for sale by broker.
Don’t miss out on this very popular Post 46 Sport Fisherman with low hours since a complete engine overhaul. Designed by Russell Post and built by Post Marine in Mays Landing, NJ, the ever-popular Post 46 was introduced in 1978 and produced through 1996. Jubilee is powered by rebuilt twin 485 HP Detroit Diesel Johnson & Towers 6-71 TIBs with just 476/361 hours since their rebuild. Her owners purchased her new in 1988 and are now ready to pass her on to her next owner.…
70 Photos
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Bertram 31

Bertram 31 (Chesapeake Bay)

Price $19,900 (USD)
Location DELTAVILLE, Virginia (Chesapeake Bay)
M/Y Parisea — a 1972 Bertram 31 Fly Bridge Cruiser, for sale by broker.
PARISEA is a classic 1972 Bertram Flybridge Cruiser in good condition, having had an extensive mechanical refit including engines, running gear, fuel system, custom fish box/live well, bonding system, and electrical systems. Nothing in power boating has equaled the continued worldwide popularity of the Bertram 31 with the legendary deep-V hull design. In addition to her superb seakeeping characteristics, the 31 FBC has a large fishing cockpit and a spartan but comfortable cabin with berths for four. Located in Deltaville, Virginia, with complete engine service just completed by Deltaville Boat Yard, she is ready to fish and cruise the Chesapeake Bay.…
48 Photos
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Great Harbour TT35

Great Harbour TT35 (Chesapeake Bay)

Price $287,900 (USD)
Location Pasadena, Maryland (Chesapeake Bay)
M/Y Dilligaf — a 2021 Great Harbour TT35, for sale by broker.
Commissioned less than four years ago, Dilligaf is a practically new Great Harbour TT35 that would cost over $400,000 to build today. The Great Harbour TT35 packs all the amenities of a comfortable liveaboard trawler into a highly versatile, trailerable boat with endless possibilities. From local gunkholing to a Great Loop adventure, the TT35 delivers. She features a center queen berth, a head with a separate shower, and a fully equipped galley. Powered by ultra-efficient twin Suzuki outboards, she can take you wherever you want to go.…
62 Photos
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Bertram 33

Bertram 33 (Chesapeake Bay)

Price $45,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)
M/Y Lady Nicole — a 1980 Bertram 33, for sale by broker.
This very well-maintained Bertram 33 is available to see in Annapolis, MD. Captain-owned and maintained, it is in very good condition and ready for its next owner. Low hours, a very clean interior, and new canvas highlight this vessel. Lady Nicole is a fine example of a well-maintained Bertram 33 Convertible and is ready for its next fishing and cruising adventure.…
21 Photos
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