Yachts For Sale in Chesapeake Bay

median sold price
$125,000
sales on record
507
years built
1938–2026
typical length
27–53 ft
for sale now
67
Grand Banks 42 Classic
$6,000 (USD) Price Drop! (Sep 6, 2026)

Grand Banks 42 Classic (Chesapeake Bay)

Asking $135,000 (USD)
Location St. Michaels, Maryland (Chesapeake Bay)
M/Y Maia is 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.…
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Tayana 37 Cutter

Tayana 37 Cutter (Chesapeake Bay)

Asking $60,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Gyatso is a 1985 Tayana 37 Cutter for sale by broker.
1985 Tayana 37 Cutter — “GYATSO” A legendary Bob Perry bluewater design — a proven offshore platform ready for restoration. Few production sailboats have earned the offshore reputation of the Tayana 37. Designed by Bob Perry and built by the renowned Ta-Yang Yacht Building Co. in Taiwan, she is a heavily built, seakindly cutter that has carried owners safely across oceans for four decades. “GYATSO” is cutter-rigged with all lines led aft to the cockpit, making her manageable for shorthanded and singlehanded passagemaking.…
10 Photos
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Hunter 336

Hunter 336 (Chesapeake Bay)

Asking $34,900 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V D. Doright is a 1995 Hunter 336 for sale by broker.
Dudley DoRight is a 1995 33′ Hunter 336 sloop. She offers a single Yanmar 27 HP auxiliary, reverse-cycle air conditioning and heating system, two hatch breeze boosters, and a two-stateroom layout with a queen-size berth in the aft stateroom.…
55 Photos
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Leopard 42 underway exterior

Leopard 42 (Chesapeake Bay)

Asking $157,777 (USD) Duty Paid Reduced!
Location Hayes, VA (Chesapeake Bay)
S/V Ahonu is a 2003 Leopard 42 for sale by owner.
S/V AHONU is a Chesapeake Bay based 2003 Leopard 42, For Sale By Owner, recently put on the hard in Virginia USA. No trades, financial settlement only. AHONU is For Sale By Owner Only / We will not pay ANY broker fee. Potential buyers are welcome to employ and pay a broker but are responsible for any fees agreed to. If you are interested, please contact the owner yourself.

Please read the entire ad before contacting. This sale is for a well-loved functional vessel, but she is not a modern technological marvel and floating castle.

…
51 Photos
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Balance 482

Balance 482 (Chesapeake Bay)

Asking $1,549,000 (USD) Duty Paid
Location Annapolis, MD, US (Chesapeake Bay)
S/V inBalance is a 2022 Balance 482 for sale by broker.
InBalance was awarded Best Multihull by Sailing World in 2022 and Best Performance Catamaran by Cruising World in 2022. Experience the catamaran that revolutionized performance cruising. US import duty paid, CBP Form 7501 in hand. Available for in-person tours during the 2026 Annapolis Sailboat Show. InBalance is hull #4 of the Balance 482, commissioned by the founder of Balance Catamarans as his personal boat and specified with nearly every factory option. She is equipped with the full Essential Performance Voyager package: retractable daggerboards, six 48-volt electric winches, and 800 amp-hours of 24-volt lithium behind a dual Integrel charging system, plus an updated five-sail arsenal of Ullman sails.…
71 Photos
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Hatteras 54

Hatteras 54 (Chesapeake Bay)

Asking $245,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)
M/Y Material Girl is 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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Catalina C320

Catalina C320 (Chesapeake Bay)

Asking $40,000 (USD)
Location Deale, Maryland (Chesapeake Bay)
Polar C is a 1996 Catalina C320 for sale by broker.
Well-loved Catalina — ready for her next adventure. We’re sad to see her go, but life has gotten busy and this beautiful Catalina deserves an owner who can give her the time on the water she’s meant for. She’s been cared for and comes fully equipped, with recent upgrades already done for you: new batteries, new water heater, updated toilet system, and new vents. All the big-ticket maintenance is handled, so you can skip the projects and get straight to enjoying her.…
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Defever 49 CPMY

Defever 49 CPMY (Chesapeake Bay)

Asking $425,000 (USD)
Location Smithfield, Virginia (Chesapeake Bay)
M/Y Sea Cow is 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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Lagoon 42 Owner’s Version
Updated! (Sep 10, 2026)

Lagoon 42 Owner’s Version (Chesapeake Bay)

Asking $399,900 (USD) Duty Paid
Location Baltimore, Maryland (Chesapeake Bay)
S/V Lagoon 42 is a 2019 Lagoon 42 Owner’s Version for sale by broker.
US Flagged • Duty Paid • 3 Cabin Owner Layout • 1,200Ah Lithium • 1,500W Solar • Watermaker • Generator • Starlink The Lagoon 42 has earned accolades from sailing magazines and is noted for great sailing performance with exceptional comfort, spacious accommodations, and straightforward systems management. This 2019 Lagoon 42 Owner Version represents an outstanding opportunity to own an extensively upgraded cruising yacht that has already received many of the improvements today’s buyers are looking for. Featuring the highly desirable 3 cabin / 3 head owner’s layout, this yacht has been thoughtfully outfitted for extended cruising with an impressive 1,200Ah lithium battery bank, 1,500 watts of solar, Victron power management, Sea Recovery watermaker, 13.5kW Onan generator, Starlink internet, upgraded sail inventory, and numerous equipment upgrades throughout.…
66 Photos
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Sea Ray 40

Sea Ray 40 (Chesapeake Bay)

Asking $219,500 (USD)
Location Pasadena, Maryland (Chesapeake Bay)
M/Y Dawn Watch is 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.…
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Jeanneau 51

Jeanneau 51 (Chesapeake Bay)

Asking $499,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Sto Lat is a 2018 Jeanneau 51 for sale by broker.
Stol-lat is a 2018 Jeanneau 51, beautifully appointed owner’s version that blends proven sailing performance with luxury cruising amenities. Designed for extended cruising or comfortable liveaboard living, this three-cabin, two-head layout features a spacious forward owner’s suite, two well-appointed aft guest cabins, and a convenient utility room with an additional refrigerator. Rich Alpi Natural Oak joinery, upgraded upholstery details, a deluxe folding salon table, Bose sound system, and salon TV create a warm and inviting interior. The well-equipped L-shaped galley is designed for extended time aboard and includes a three-burner stove with oven, microwave, dishwasher, refrigerator, hot water system, and a second refrigerator located in the utility room for additional cold storage.…
30 Photos
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FP Belize 43

FP Belize 43 (Chesapeake Bay)

Asking $199,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Destiny II is a 2000 Fountaine Pajot FP Belize 43 for sale by broker.
Destiny II is for sail. Enjoy the exhilaration of tactical sailing with the comfort of home. Bring family and friends for day sails and long-term cruising. This Fountaine Pajot Belize 43 has a new mast and rigging, manufactured in 2025 by US Spars and installed by the professionals at St. Augustine Marine Center. The team worked closely to ensure that all specs were tailored to Destiny II. This included boom, crossbeam, sail car track, hardware, rope clutches, running rigging, standing rigging, and tuning of the rig.…
25 Photos
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Scanmar 35

Scanmar 35 (Chesapeake Bay)

Asking $38,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V Sante is a 1985 Scanmar 35 for sale by broker.
Sante is a 1985 35′ Scanmar sloop. She offers a 2003 Yanmar 28 HP auxiliary, reverse cycle air conditioning/heating system, radar, large cockpit and a two-stateroom layout.…
43 Photos
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Sabre 42 Flybridge

Sabre 42 Flybridge (Chesapeake Bay)

Asking $375,000 (USD)
Location Chesapeake, Virginia (Chesapeake Bay)
M/Y Lucille is a 2006 Sabre 42 Flybridge for sale by broker.
Lucille is a 2005 42′ Sabre flybridge model. She offers twin Yanmar 500 HP main engines, Onan 11.5 kW generator, Xantrex 3,000-watt inverter, galvanic isolator, Side-Power bow and stern thrusters, oil change system, 2023 AB aluminum hull tender and a 2-stateroom layout. With her attainable 13’5" height, Lucille is a perfect Great Loop candidate.…
75 Photos
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Fountaine Pajot Lipari 41
Sale
Pending

Fountaine Pajot Lipari 41 (Chesapeake Bay)

Asking $290,000 (USD)
Location Cape Charles, VA, US (Chesapeake Bay)
S/V Apple Pie is a 2013 Fountaine Pajot 41 Lipari for sale by broker.
Apple Pie is a beautifully maintained 2013 Fountaine Pajot Lipari 41 Owner’s Version, thoughtfully equipped for comfortable liveaboard cruising and extended offshore adventures. The highly sought-after three-cabin, two-head owner’s layout offers a spacious owner’s hull, an inviting salon with panoramic views, and an open cockpit that seamlessly blends indoor and outdoor living. Designed by Joubert-Nivelt and built by Fountaine Pajot, the Lipari 41 is renowned for its efficient performance under sail, comfortable accommodations, and ease of handling, making it an excellent choice for couples or families looking to cruise with confidence.…
Fountaine Pajot Lipari 41 Details
Pearson 35 Sloop

Pearson 35 Sloop (Chesapeake Bay)

Asking $19,500 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V Lucky Dog is a 1979 Pearson Sloop for sale by broker.
Lucky Dog is a 1979 35′ Pearson sloop. She offers a Westerbeke 30 HP auxiliary, C-Marine bowthruster, Raymarine multi-function display, Autohelm autopilot, Harken roller furler, Mack Sails mainsail stack pack and a Sylvester 7′ inflatable tender with a Mercury 2.5 HP outboard.…
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Hatteras 48 LRC

Hatteras 48 LRC (Chesapeake Bay)

Asking $199,500 (USD)
Location Poquoson, Virginia (Chesapeake Bay)
M/Y Overdraft is 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.…
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Fountaine Pajot 41 Lipari

Fountaine Pajot 41 Lipari (Chesapeake Bay)

Asking $295,000 (USD)
Location Chestertown, Maryland (Chesapeake Bay)
S/V Irish Rover is a 2012 Fountaine Pajot 41 Lipari for sale by broker.
The 2012 Fountaine Pajot Lipari 41 is a proven cruising catamaran that has been thoughtfully upgraded and is ready for its next adventure. Previously operated in charter, she has been privately owned and out of charter service for the past five years, during which time she has received numerous upgrades focused on reliability, comfort, and extended cruising. Designed for sailors seeking an efficient and comfortable liveaboard or cruising platform, this Lipari 41 is exceptionally well-equipped for coastal passages, the Intracoastal Waterway, and Caribbean island hopping.…
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Lagoon 560
Updated! (Sep 9, 2026)

Lagoon 560 (Chesapeake Bay)

Asking $848,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)
S/V CASCADIA 2 is a 2012 Lagoon 560 for sale by broker.
Duty paid. 2012 Lagoon 560 “Cascadia 2.” Two owners | Never chartered. This 2012 Lagoon 560 catamaran, CASCADIA 2, is tailored for discerning sailors, delivering a blend of performance, luxury, and style. Offered in turnkey condition for immediate entertaining or chartering, she accommodates up to 10 guests across five elegant staterooms. The interior showcases premium craftsmanship, blending sophisticated design with everyday comfort. Each private stateroom acts as a peaceful haven, complete with deluxe bedding and an en-suite bathroom for a restful stay after a day on the water.…
124 Photos
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Xquisite X5

Xquisite X5 (Chesapeake Bay)

Asking $890,000 (USD) Duty Paid
Location Edgewater, Maryland (Chesapeake Bay)
Chi is a 2016 Xquisite Xquisite X5 for sale by broker.
CHI was designed by renowned naval architect Rudolf Jonker and built in South Africa by Phoenix Marine Manufacturing. This 2016 Xquisite X5 Owner’s Version delivers the perfect balance of luxury, performance, and offshore capability and is fully stocked and ready to sail away. Featuring the highly sought-after three-cabin, three-head owner’s layout, the starboard hull is dedicated to an expansive owner’s suite, while two spacious guest cabins provide exceptional comfort and privacy. The bright salon is surrounded by panoramic windows and seamlessly connects to a gourmet galley equipped with premium small appliances, generous refrigeration, a dishwasher, and abundant storage, making extended cruising effortless.…
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Lagoon 380

Lagoon 380 (Chesapeake Bay)

Asking $219,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)
S/V Heaven is a 2003 Lagoon 380 for sale by broker.
Rare opportunity to purchase an Owners Version of a popular Lagoon 38 with extensive upgrades! Heaven features air conditioning, separate shower station, raised Bimini, as well as a custom helm seat for added comfort. Its grand interior volume veils the fast and seaworthy hulls. This vessel is ready to cruise the Bahamas and beyond! The Lagoon 380 owners version (3 cabins/2 heads) catamaran is a very comfortable, livable and manageable yacht. The owners cabin is in the starboard hull with a full bath forward, a large queen berth aft and desk and storage lockers in between.…
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Fountaine Pajot Saona 47

Fountaine Pajot Saona 47 (Chesapeake Bay)

Asking $765,000 (USD)
Location Mathews, VA, US (Chesapeake Bay)
S/V ILE DE REY is a 2020 Fountaine Pajot Saona 47 for sale by broker.
The 2020 Fountaine Pajot Saona 47 Maestro ILE DE REY represents a significantly upgraded, offshore-capable cruising platform that sits well above standard production specifications. Privately owned and never chartered, the vessel has been configured for serious long-range autonomy. Combining rare Yanmar 4JH57 propulsion with a high-capacity Victron lithium energy system, extensive solar generation, hydro-generation and a 12 kW Fischer Panda generator, the result is a genuinely self-sufficient electrical architecture capable of supporting heavy loads, including air conditioning, watermaker operation (generator only), and domestic appliances, without reliance on shore power or continuous generator use.…
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Tayana 37 Cutter

Tayana 37 Cutter (Chesapeake Bay)

Asking $45,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V Three Little Birds is a 1983 Tayana 37 Cutter for sale by broker.
Three Little Birds is a 1983 37′ Tayana Cutter. She offers a Yanmar 30 HP auxiliary, Victron Energy 3,000 watt inverter, solar panels, watermaker, aluminum radar arch, and a ProFurl roller furler. Her sellers have bought their new boat, so Three Little Birds is seriously for sale to her next bluewater cruising buyer.…
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Leopard 48
$14,000 (USD) Price Drop! (Sep 9, 2026)

Leopard 48 (Chesapeake Bay)

Asking $475,000 (USD) Duty Paid Reduced!
Location Annapolis, Maryland (Chesapeake Bay)
S/V WHITE WINGS is a 2013 Leopard 48 Family Layout for sale by broker.
WHITE WINGS represents the ideal combination of one of the world’s most successful cruising catamaran designs and an owner who spared no expense in making her truly cruise-ready. Thoughtfully upgraded, meticulously maintained, and proven on extensive voyages throughout the Caribbean and up the U.S. East Coast to Maine, she is ready for her next adventure. If you’re searching for a capable offshore cruising catamaran with the systems and equipment already in place, WHITE WINGS deserves your attention. Designed for comfortable cruising away from the dock, she features a robust off-grid power system including a large lithium battery bank, a substantial solar array, modern solar controllers, a high-capacity inverter/charger, upgraded alternators, and DC-DC charging solutions.…
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Bali 4.1

Bali 4.1 (Chesapeake Bay)

Asking $440,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)
S/V Lagertha is a 2018 Bali 4.1 for sale by broker.
Its spacious saloon, worthy of a much larger boat; its tilting door, which was incredibly easy to operate; its forward cockpit offering a large additional living space for the whole family; and the overall smart design choices made by BALI were the elements that convinced us the most.…
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Morgan 43

Morgan 43 (Chesapeake Bay)

Asking $64,900 (USD)
Location Pasadena, MD (Chesapeake Bay)
Windswept is a 1987 Morgan 43 for sale by broker.
1987 Morgan 43’ Sailboat – Well Equipped Cruiser Spacious and capable 1987 Morgan 43’ sailboat designed for comfortable coastal cruising or extended liveaboard use. This vessel has extensive onboard systems and cruising upgrades that enhance comfort and practicality for extended stays aboard. The galley is equipped with a propane three-burner stove with oven, making the boat comfortable for extended cruising or liveaboard use. This Morgan 43 is outfitted with many of the systems serious cruisers look for, including maneuverability, upgraded electrical capability, modern navigation electronics, and comfortable galley amenities.…
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Leopard 46

Leopard 46 (Chesapeake Bay)

Asking $349,000 (USD)
Location EDGEWATER, MARYLAND (Chesapeake Bay)
Sandpiper is a 2007 Leopard 46 for sale by broker.
Sandpiper is a 2007 Leopard 46 catamaran designed by renowned naval architects Morelli & Melvin and built by Robertson & Caine. Featuring the highly sought-after four-cabin layout, she offers spacious accommodations, excellent ventilation, and a comfortable salon ideal for extended cruising or liveaboard use. Recent upgrades and servicing completed in 2025 include rebedded hatches, bow hardware, and through-hulls; new bilge check valves; updated deck fittings; additional interior shelving; and head system servicing. Safety and reliability updates include a replacement anchor locker gas strut and a new EPIRB battery.…
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TRT 1200 CR
$16,000 (USD) Price Drop! (Sep 11, 2026)

TRT 1200 CR (Chesapeake Bay)

Asking $169,000 (USD) Duty Paid Reduced!
Location Easton, Maryland (Chesapeake Bay)
S/V Nemo is a 2002 TRT 1200cr for sale by owner.
This well equipped TRT catamaran cruiser/racer version is offered for sale by the original owner since launch and is arguably the best equipped TRT1200 ever available on the market. It is a fast yet comfortable and lightweight boat that has been well cared for and upgraded over the years. Construction is Divinycell closed cell foam and vinyl-ester resin. Hulls are solid fiberglass laminate below the waterline. Decks are curved for strength and stiffness and coated with tough and safe nonskid two part poly urethane.…
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Rival 41

Rival 41 (Chesapeake Bay)

Asking $87,500 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Firelight is a 1982 Rival 41 for sale by broker.
Firelight is a classic 1982 41′ Rival 41AC designed by Peter Brett and built by Southern Boatbuilding in Southampton, UK. She is a one-owner boat and has done a circumnavigation via Panama and the Red Sea, sailed the entire U.S. east coast several times, and spent many years cruising in the Bahamas. She has proven to be seaworthy, reliable, and comfortable, and she has been admired wherever she goes. She was built to Lloyd’s Maltese Cross +100A1 standards.…
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Nordic Tugs 32
Sale
Pending

Nordic Tugs 32 (Chesapeake Bay)

Asking $119,000 (USD)
Location Chester, Maryland (Chesapeake Bay)
M/Y North Star is a 2000 Nordic Tugs 32 Pilothouse Trawler for sale by broker.
“North Star” is a clean, well-maintained 20th Anniversary Edition Nordic Tug 32′ Pilothouse, a two-owner vessel that has been meticulously maintained by her capable owner. With her dependable diesel engine, known as the “Million Mile Engine” for its longevity, she has been a reliable, turn-key trawler with timeless lines and trusted performance. “North Star” has completed the Great Loop, traveled the ICW, and undertaken extended island hopping. Her bottom is repainted yearly.…
Nordic Tugs 32 Details
Arrow 1280 S

Arrow 1280 S (Chesapeake Bay)

Asking $977,000 (USD)
Location King George, VA, US (Chesapeake Bay)
S/V Arrow 1280 S is a 2026 Schionning Arrow 1280 S for sale by broker.
This high-tech vessel is currently under construction and nearly completed. It can be bought outright as a finished vessel, or we can finish the boat to your spec. Please call for current pricing and check out the build process on the website or follow here. Ojigwan Yachts specializes in yacht building featuring custom composite construction and fabrication. We do vacuum infusion, wet lamination under vacuum, and typical resin/fiberglass layup. We use carbon fiber and fiberglass construction and primarily use epoxy resin.…
112 Photos
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Lagoon 39

Lagoon 39 (Chesapeake Bay)

Asking $299,000 (USD) Duty Paid
Location Annapolis, MD, US (Chesapeake Bay)
S/V Cecil is a 2014 Lagoon 39 for sale by broker.
2014 Lagoon 39 Cecil 4-Cabins 2-Heads U.S. Duty Paid | Energy Independence | Enhanced Onboard Amenities Cecil is an exceptionally well-equipped 2014 Lagoon 39, a model renowned for its spacious 4-cabin layout, comfortable sailing performance, and efficient owner-friendly design. With an ICW-friendly 626 mast height, she is equally suited for coastal cruising and offshore adventure. She stands apart from others on the market thanks to significant 2024 upgrades focused on energy efficiency and liveaboard comfort. A comprehensive electrical refit introduced 920Ah of lithium batteries, 2,240W of bifacial solar on a custom offshore arch, Victron monitoring, dual MultiPlus inverters, and high-output alternators, all delivering outstanding off-grid capability and modern power management.…
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President 43
$5,950 (USD) Price Drop! (Sep 8, 2026)

President 43 (Chesapeake Bay)

Asking $62,000 (USD)
Location Baltimore, Maryland (Chesapeake Bay)
Valkomenn is 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.…
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Endeavour 37 Plan A

Endeavour 37 Plan A (Chesapeake Bay)

Asking $37,500 (USD)
Location Norfolk, Virginia (Chesapeake Bay)
S/V Seagull is a 1981 Endeavour 37 Plan A for sale by broker.
Seagull is a 1981 Endeavor 37′ in above-average condition. Endeavors are widely regarded as “built like a tank” cruisers that prioritize interior living space and solid construction over speed. The current owner bought her new and has sailed her to the Bahamas and Caribbean. At 45 years old, she is mature but has years of life left for her next owner. She is rigged for single-handed sailing. Seagull is a Plan A model, which has an open interior concept that enhances socializing and long-term cruising, with a private master stateroom aft to starboard.…
47 Photos
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Ocean Alexander 50 Mark II Pilothouse

Ocean Alexander 50 Mark II Pilothouse (Chesapeake Bay)

Asking $119,000 (USD)
Location Suffolk, Virginia (Chesapeake Bay)
M/Y Surprise is a 1986 Ocean Alexander 50 Mark II Pilothouse for sale by broker.
Surprise is in good condition. She has been owned by the seller for 20 years and has 3 staterooms, 2 full heads, a spacious galley, and a roomy, attractive salon. The pilothouse has great visibility and easy access to the side decks for docking. The flybridge is large. Approximately 5 engine hours have been logged since Surprise was in the yard for engine service and bottom paint in 2025.…
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Fountaine Pajot FP Isla 40

Fountaine Pajot FP Isla 40 (Chesapeake Bay)

Asking $479,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Amihan is a 2023 Fountaine Pajot FP Isla 40 for sale by broker.
Amihan is a turnkey, extensively upgraded Fountaine Pajot Maestro (3-cabin/3-head) catamaran—a true owner’s version designed by Berret-Racoupeau Yacht Design. This vessel blends performance sailing with exceptional liveaboard comfort. The spacious layout features a bright salon, a fully equipped galley, and private ensuite cabins. The owner’s suite includes battery-powered A/C for quiet, off-grid comfort. Energy independence is unmatched with extensive lithium battery capacity, a substantial solar array, advanced charging systems, and a watermaker. Additional systems provide backup power and conveniences for extended cruising.…
44 Photos
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Lagoon 42

Lagoon 42 (Chesapeake Bay)

Asking $499,000 (USD)
Location Norfolk, VA, US (Chesapeake Bay)
S/V Neptune's Waters is a 2019 Lagoon 42 for sale by broker.
Neptune’s Waters is an exceptional value, a highly desirable owner’s version layout of the ultra-popular Lagoon 42. Neptune’s Waters is equipped with a deck-stepped, fractional-rigged mast and wire rigging, and is powered by a pair of 4-cylinder Yanmar diesel engines with Yanmar saildrives. She features a three-stateroom, three-head layout with a large salon and spacious cockpit.…
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Lagoon 420
$11,000 (USD) Price Drop! (Sep 1, 2026)

Lagoon 420 (Chesapeake Bay)

Asking $299,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Apres Sea is a 2008 Lagoon 420 for sale by broker.
Après Sea and located in Annapolis, MD, this beautifully equipped 2008 Lagoon 420 Owner’s Version catamaran is an outstanding opportunity for comfortable cruising or full-time liveaboard life. Spacious, safe, and easy to sail, Après Sea offers three cabins and three heads, with the entire port hull dedicated to a private owner’s suite featuring an island queen berth, lounge seating, desk, generous storage, and a large ensuite with separate shower. Two guest cabins to starboard each include island-style berths and private heads—perfect for family and guests.…
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Atlantic 42 Custom

Atlantic 42 Custom (Chesapeake Bay)

Asking $430,000 (USD)
Location Deltaville, VA, US (Chesapeake Bay)
S/V Watermark is a 2003 Chris White Atlantic 42 for sale by broker.
2003 Chris White Atlantic 42 “Watermark” Watermark is a rare, meticulously maintained example of the legendary Atlantic 42 performance catamaran. Built by the respected Lombardi Yachts, she embodies the Chris White philosophy of speed, safety, and ease of handling. Unlike many vessels of this vintage, Watermark has undergone a comprehensive refit and continuous upgrade cycle from 2019 through 2025. With new Yanmar engines (2022), updated saildrives, and a complete electronics and power overhaul, she is a turn-key offshore machine. Since 2022, she has been dry-sailed, preserving the hull and machinery in top-tier condition.…
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Fountaine Pajot Athena 38

Fountaine Pajot Athena 38 (Chesapeake Bay)

Asking $119,000 (USD) Reduced!
Location Deltaville, VA (Chesapeake Bay)
S/V Andiamo is a 1996 Fountaine Pajot 38 Athena for sale by owner.
Serious inquiries only, no keel kickers please.  If you’re  6’ or taller, headroom is not ideal. Many upgrades over the winter including Blackstone engine oil analysis and compression tests to give a clear picture of engine health. This vessel has been thoughtfully converted from its original layout to a spacious 3-cabin configuration, providing an expansive owner’s suite with a large shower and an enhanced navigation/workspace area—ideal for those seeking comfort, versatility, and functionality. The Athena 38 is renowned for its performance, reliability, and easy handling, making it a favored choice among bluewater cruisers and coastal sailors alike.…
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S2 C36

S2 C36 (Chesapeake Bay)

Asking $26,750 (USD)
Location St. Michaels, Maryland (Chesapeake Bay)
S/V Remedy is a 1981 S2 C36 for sale by broker.
Remedy is a 1981 36′ S2 C36, a center‑cockpit cruising yacht that pairs rugged S2 construction with a thoughtfully arranged interior. Her layout is geared toward comfortable cruising and liveaboard use, with an especially private aft master stateroom featuring a queen‑size berth—an uncommon level of sleeping comfort for a 36‑footer. The center‑cockpit configuration yields separation between owner and guest accommodations and provides a protected, elevated helm position with excellent sightlines. The C36 is known for efficient use of interior volume: you’ll typically find a roomy salon with generous headroom, a functional galley suitable for extended passages, and a dedicated navigation station—features that make provisioning, passage planning and daily living aboard straightforward.…
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Beneteau 373

Beneteau 373 (Chesapeake Bay)

Asking $89,500 (USD)
Location North Beach, Maryland (Chesapeake Bay)
S/V Cool Breeze is a 2007 Beneteau 373 for sale by broker.
Cool Breeze is a 2007 37′ Beneteau 373 model. She has a two-stateroom layout. Cool Breeze has just been detailed and is accessible for inspection.…
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Custom 65

Custom 65 (Chesapeake Bay)

Asking $300,000 (USD)
Location Saint Michaels, Maryland (Chesapeake Bay)
M/Y Choptank is 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.…
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Leopard 38
Updated! (Sep 10, 2026)

Leopard 38 (Chesapeake Bay)

Asking $219,000 (USD) Duty Paid Reduced!
Location Deale, Maryland (Chesapeake Bay)
S/V WAY MAKER is a 2010 Leopard 38 for sale by broker.
In a world of ever-increasing prices and where the marine industry charges by the foot, a reliable cruising platform in a smaller form factor makes great sense for those of us looking to manage costs. Welcome aboard WAY MAKER, a 2010 Leopard 38 sailing catamaran located in Deale, MD. The Leopard 38 won accolades from the major sailing publications upon her debut in 2010. They have continued to be solid performers and, with less than 4 feet of draft, are perfect for gunkholing around the Chesapeake, exploring the backcountry of the Florida Keys, or getting in close to the beautiful beaches of the Bahamas.…
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Morrelli and Melvin 46 Custom exterior exterior

Morrelli and Melvin 46 Custom (Chesapeake Bay)

Asking $299,500 (USD) Survey
Location Hampton, VA (Chesapeake Bay)
S/V Rhatcat is a 2003 Morrelli and Melvin 47 Custom for sale by owner.

Yacht survey by Coastal Marine LLC. 5/20/22 at Key Largo FL. during our haul-out. ($438,800 Survey Market Value)

Rhatcat is an Morrelli and Melvin 46 design catamaran for sale by owner.  She is a liveaboard / cruiser with 26’ beam (wider is better). Built with the cruising couple in mind that can easily be singlehanded.

Yacht designers Morrelli and Melvin are known for performance catamarans.  Rhatcat is typical, reaching 17 knots plus.…

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Leopard 43

Leopard 43 (Chesapeake Bay)

Asking $250,000 (USD) Reduced!
Location Galesville, Maryland (Chesapeake Bay)
S/V ESCAPE is a 2006 Leopard 43 for sale by owner.
10/31/2025 Update: ESCAPE was hauled out this week for some maintenance.  The bottom was cleaned and repainted, two new props were installed and three through-hull/sea-cocks where replaced. Last month one of the two AC units was replaced with a new unit. Presenting an exceptional opportunity to own a 2006 Leopard 43 catamaran, a celebrated model renowned for its robust build, outstanding performance, and comfortable living spaces. This vessel masterfully combines the innovative design and superior craftsmanship that have made Leopard Catamarans a top choice among discerning sailors worldwide.…
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Bristol 35.5
$5,500 (USD) Price Drop! (Aug 31, 2026)

Bristol 35.5 (Chesapeake Bay)

Asking $74,500 (USD)
Location Annpolis, Maryland (Chesapeake Bay)
S/V Skye is a 1986 Bristol 35.5C for sale by broker.
Skye is a 1986 35′ Bristol 35.5C in very nice condition. She offers a Universal 35 HP auxiliary and numerous updates, including new standing rigging in 2022, new running rigging in 2022, new lazy jacks in 2022, a new wire harness in 2022, barrier coat and anti-fouling in 2022, a new Garmin multi-function display and NavPod in 2022, Awlgrip paint in 2022, a new mainsail and genoa in 2022, a new Kuuma water heater in 2024, a new Seagull filtered freshwater faucet in 2024, a new dodger and mainsail cover in 2025, a new Max-Prop in 2025, and a new cutlass bearing in 2025.…
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Beneteau Oceanis 381

Beneteau Oceanis 381 (Chesapeake Bay)

Asking $59,000 (USD)
Location Tracy's Landing, Maryland (Chesapeake Bay)
S/V Little Wing is a 1998 Beneteau Oceanis 381 for sale by broker.
Little Wing is a well-kept 1998 Beneteau Oceanis 381 measuring 38′ overall, offered for sale. This proven cruiser combines comfortable liveaboard accommodations with straightforward, confidence-inspiring sailing characteristics. The hull and deck are production fiberglass construction, built to Beneteau standards for durability and volume. Below, Little Wing features a two-stateroom layout with queen-size berths in each cabin, providing generous sleeping accommodations for family or guests. The interior is arranged for practical cruising: an open salon, a well-proportioned galley suitable for extended passages, a dedicated navigation area, and an enclosed head.…
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