Sailboats For Sale in Chesapeake Bay

( 51 Results )

Nautitech 395 Prestige Edition (Chesapeake Bay)

Price $160,000 (USD)
Location Cape Charles, Virginia (Chesapeake Bay)
Phoenician — a 2000 Nautitech 395 Prestige Edition, for sale by broker.
2000 Dufour Nautitech 395 Owner’s Version, 3 cabins and 2 heads. Well kept and never chartered. The starboard hull is devoted entirely to the master suite with a house-sized head and shower, and a large stand-up storage locker in the bow. This is a real sailboat that crossed the Atlantic Ocean from Nautitech in France to the Miami Boat Show, where she was first sold. She is capable of 15 knots on a beam reach and can point as high as 30 degrees.…
20 Photos Contact Broker

Leopard 45 Lounge (Chesapeake Bay)

Price $779,000 (USD) Duty Paid
Location Annapolis, MD (Chesapeake Bay)
S/V Radiant Hope — a 2021 Leopard 45 Lounge, for sale by owner.

Private showings in Annapolis during boat show week, October 8–18, 2026. Radiant Hope lies at Annapolis Safe Harbor, a short walk from City Dock, the Powerboat Show and the Sailboat Show. Call or text and I’ll set up a time to show you aboard.

Radiant Hope is a 2021 Leopard 45 Lounge in the three-cabin Owner’s Version, built by Robertson & Caine to a Simonis Voogd design. We are her original owners, and we are selling her ourselves, with no broker.…

46 Photos Contact Owner

Leopard 50 Owners Version (Chesapeake Bay)

Price $1,125,000 (USD) Duty Paid
Location Annapolis, Maryland, US (Chesapeake Bay)
S/V Good Day — a 2023 Leopard 50 Owners Version, for sale by broker.
2023 Leopard 50 Owner’s Version “Good Day” – 3-cabin layout plus utility room | U.S. import duty paid | Privately owned and never chartered. First look – available in Annapolis, Maryland – coming soon to Fort Lauderdale, Florida She has the latest upgrades and everything you need to set sail today for long-term cruising.…
13 Photos Contact Broker

FP 40 ISLA (Chesapeake Bay)

Price $460,000 (USD) Duty Paid
Location Deltaville, VA (Chesapeake Bay)
S/V Amihan — a 2023 Fountaine Pajot 40 ISLA, for sale by owner.

Step aboard Amihan and you’ll see why the Isla 40 has become one of the most talked-about cruising catamarans in its size range. Berret-Racoupeau Yacht Design drew her to replace the popular Lucia 40, and she improves on it with a bright, open saloon, a well-organized galley, a comfortable cockpit, and good sightlines from the helm. She is the Maestro layout, with three cabins and three heads. The full owner’s hull gives you a private suite with an ensuite head and generous storage, and two guest cabins, each with its own head, occupy the opposite hull.…

65 Photos Contact Owner

Nonsuch 30 Ultra (Chesapeake Bay)

Price $39,000 (USD)
Location Mayo, MD (Chesapeake Bay)
S/V Little Wing — a 1987 Nonsuch 30 Ultra, for sale by broker.
GLASS DECKS! Here’s your chance! “Little Wing” is a nice example of what Hinterhoeller used to refer to as “the greatest thirty-foot sailboat of all time.” Her quality construction is apparent everywhere you look, and her sailing abilities will surprise you. Most sailors are surprised by the roomy interior, aided by a nice wide beam and the mast placement forward. With an exceptional interior including a large L-shaped galley, oversized quarter berth, luxurious main salon and a wonderfully comfortable forward owner’s stateroom, “Little Wing” is one of the best of the legendary 30′ Nonsuch Ultra sailboats to come on the brokerage market.…
22 Photos Contact Broker

Leopard 46 (Chesapeake Bay)

Price $390,000 (USD) VAT & Duty Paid
Location Solomons, MD (Chesapeake Bay)
S/V Numa — a 2008 Leopard 46, for sale by owner.

2008 Leopard 46 Owner’s Version – Extensively Upgraded

Numa is a 2008 Leopard 46 Owner’s Version that has had only two owners since new. The original owner commissioned the boat and maintained her exclusively for private use before we purchased her in 2020. For the past six years, she has served as our full-time home and cruising vessel as we explored the U.S. East Coast, Bahamas, and Caribbean while continuously maintaining and upgrading her systems and equipment.…

35 Photos Contact Owner

Tayana 37 Cutter (Chesapeake Bay)

Price $60,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Gyatso — 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 Contact Broker

Hunter 336 (Chesapeake Bay)

Price $34,900 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V D. Doright — 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 Contact Broker

Balance 482 (Chesapeake Bay)

Price $1,549,000 (USD) Duty Paid
Location Annapolis, MD, US (Chesapeake Bay)
S/V inBalance — 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 Contact Broker

Catalina C320 (Chesapeake Bay)

Price $40,000 (USD)
Location Deale, Maryland (Chesapeake Bay)
Polar C — 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.…
25 Photos Contact Broker

Lagoon 42 Owner’s Version (Chesapeake Bay)

Price $399,900 (USD) Duty Paid
Location Baltimore, Maryland (Chesapeake Bay)
S/V Lagoon 42 — 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 Contact Broker

Jeanneau 51 (Chesapeake Bay)

Price $479,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Sto Lat — 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 Contact Broker

FP Belize 43 (Chesapeake Bay)

Price $194,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)
Destiny II — 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 Contact Broker

Scanmar 35 (Chesapeake Bay)

Price $38,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V Sante — 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 Contact Broker

Pearson 35 Sloop (Chesapeake Bay)

Price $19,500 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V Lucky Dog — 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.…
54 Photos Contact Broker

Fountaine Pajot 41 Lipari (Chesapeake Bay)

Price $295,000 (USD)
Location Chestertown, Maryland (Chesapeake Bay)
S/V Irish Rover — a 2012 Fountaine Pajot 41 Lipari, for sale by broker.
2012 FP Lipari 41, extensively upgraded and cruise-ready. Ideal for ICW and Caribbean cruising. 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 well equipped for coastal passages, the Intracoastal Waterway, and Caribbean island hopping.…
24 Photos Contact Broker

Xquisite X5 (Chesapeake Bay)

Price $880,000 (USD) Duty Paid
Location Edgewater, Maryland (Chesapeake Bay)
Chi — 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.…
45 Photos Contact Broker

Lagoon 380 (Chesapeake Bay)

Price $199,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)
S/V Heaven — 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.…
61 Photos Contact Broker

Fountaine Pajot Saona 47 (Chesapeake Bay)

Price $739,000 (USD) VAT Paid
Location Mathews, VA, US (Chesapeake Bay)
S/V ILE DE REY — a 2020 Fountaine Pajot Saona 47, for sale by broker.
Price reduced to $739,000. Come see her while you are in the area for the Annapolis Boat Show. 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 (2.375 kW), 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.…
97 Photos Contact Broker

Tayana 37 Cutter (Chesapeake Bay)

Price $39,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V Three Little Birds — 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.…
58 Photos Contact Broker

Leopard 48 (Chesapeake Bay)

Price $475,000 (USD) Duty Paid Reduced!
Location Annapolis, Maryland (Chesapeake Bay)
S/V WHITE WINGS — 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.…
94 Photos Contact Broker

Bali 4.1 (Chesapeake Bay)

Price $429,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)
S/V Lagertha — a 2018 Bali 4.1, for sale by broker.
The Bali 4.1 Lagertha is located in Annapolis, MD. This is a very special owner’s version that has never been chartered and has gone through many aftermarket modifications, making it a turnkey Bali 4.1 ready for its next adventure. Its spacious saloon, worthy of a much larger boat; its tilting door, which is 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.…
23 Photos Contact Broker

Hylas 48 (Chesapeake Bay)

Price $1,724,571 (USD)
Location Bert Jabins Yacht Yard, Annapolis, Maryland (Chesapeake Bay)
S/V Hull 5 — a 2027 Hylas H48, for sale by broker.
The Hylas H48 blends Bill Dixon’s modern design with classic bluewater capability. With a safe center cockpit, bright raised-salon interior, and versatile three-cabin layout, she delivers comfort, confidence, and performance for voyagers seeking a world-ready midsize yacht. The “First in Class” Hylas H48 design has been the choice of voyagers in midsize yachts for decades and for very good reasons. Bill Dixon’s lifestyle enhancements will keep this yacht relevant for aspiring voyagers in years to come. Extending the enclosed center cockpit accommodates crew numbers and cockpit relaxation.…
18 Photos Contact Broker

Outremer 51 (Chesapeake Bay)

Price $1,149,000 (USD) Duty Paid
Location Solomons, MD, US (Chesapeake Bay)
S/V HELIA2 — a 2022 Outremer 51, for sale by broker.
2022 Outremer 51 HELIA2 | Hull #91 U.S. duty paid The ultimate family cruiser Owners version | 3 staterooms | 2 heads HELIA2 stands apart from most examples of her model, featuring two of the three primary structural upgrade options offered by Outremer: carbon bulkheads and a composite compression beam. Both materially enhance rigidity, reduce weight, and improve offshore performance, and are among the most significant structural options available from the builder. She was launched in La Grande-Motte, France, in January 2022.…
120 Photos Contact Broker

Morgan 43 (Chesapeake Bay)

Price $59,900 (USD)
Location Pasadena, MD (Chesapeake Bay)
Windswept — 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.…
29 Photos Contact Broker

Leopard 46 (Chesapeake Bay)

Price $339,000 (USD)
Location EDGEWATER, MARYLAND (Chesapeake Bay)
Sandpiper — 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.…
56 Photos Contact Broker

TRT 1200 CR (Chesapeake Bay)

Price $169,000 (USD) Duty Paid Reduced!
Location Easton, Maryland (Chesapeake Bay)
S/V Nemo — 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.…
41 Photos Contact Owner

Rival 41 (Chesapeake Bay)

Price $87,500 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Firelight — a 1982 Rival 41, for sale by broker.
1982 41′ Rival 41 Cutter. Norwegian flag/US duty paid/imported. Lloyd’s Maltese Cross +100A1. 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 completed a circumnavigation via Panama and the Red Sea, sailed the entire U.S. East Coast up and down 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.…
106 Photos Contact Broker

Arrow 1280 S (Chesapeake Bay)

Price $977,000 (USD)
Location King George, VA, US (Chesapeake Bay)
S/V Arrow 1280 S — 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 Contact Broker

Lagoon 39 (Chesapeake Bay)

Price $285,000 (USD) Duty Paid
Location Annapolis, MD, US (Chesapeake Bay)
S/V Cecil — a 2014 Lagoon 39, for sale by broker.
2014 Lagoon 39 “Cecil” Cecil is an exceptionally well-equipped 2014 Lagoon 39, a model renowned for its spacious four-cabin layout, comfortable sailing performance, and efficient, owner-friendly design. With an ICW-friendly 62’6″ 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.…
130 Photos Contact Broker

Endeavour 37 Plan A (Chesapeake Bay)

Price $37,500 (USD)
Location Norfolk, Virginia (Chesapeake Bay)
S/V Seagull — a 1981 Endeavour 37 Plan A, for sale by broker.
SEAGULL is a 1981 Endeavour 37 Plan A, sloop-rigged, with a rebuilt Perkins 4-108 50 hp engine. Her draft is 5 ft and beam 15 ft. She has Aries self-steering, a PUR 80 GPD watermaker, a Hyde roller-furling mainsail, Harken jib furling, a wind generator, replaced fuel and water tanks, and a barrier-coated hull. Seagull is a 1981 Endeavour 37 in above-average condition. Endeavours are widely regarded as “built like a tank” cruisers that prioritize interior living space and solid construction over speed.…
47 Photos Contact Broker

Lagoon 42 (Chesapeake Bay)

Price $499,000 (USD)
Location Norfolk, VA, US (Chesapeake Bay)
S/V Neptune's Waters — 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.…
133 Photos Contact Broker

Atlantic 42 Custom (Chesapeake Bay)

Price $430,000 (USD)
Location Deltaville, VA, US (Chesapeake Bay)
S/V Watermark — 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.…
141 Photos Contact Broker

Fountaine Pajot Athena 38 (Chesapeake Bay)

Price $119,000 (USD) Reduced!
Location Deltaville, VA (Chesapeake Bay)
S/V Andiamo — 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.…
41 Photos Contact Owner

Beneteau 373 (Chesapeake Bay)

Price $89,500 (USD)
Location North Beach, Maryland (Chesapeake Bay)
S/V Cool Breeze — 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.…
73 Photos Contact Broker

Leopard 38 (Chesapeake Bay)

Price $219,000 (USD) Duty Paid Reduced!
Location Deale, Maryland (Chesapeake Bay)
S/V WAY MAKER — 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.…
42 Photos Contact Broker

Morrelli and Melvin 46 Custom (Chesapeake Bay)

Price $299,500 (USD) Survey
Location Hampton, VA (Chesapeake Bay)
S/V Rhatcat — 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.…

33 Photos Contact Owner

Leopard 43 (Chesapeake Bay)

Price $250,000 (USD) Reduced!
Location Galesville, Maryland (Chesapeake Bay)
S/V ESCAPE — 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.…
35 Photos Contact Owner

Bristol 35.5 (Chesapeake Bay)

Price $69,000 (USD)
Location Annpolis, Maryland (Chesapeake Bay)
S/V Skye — 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.…
67 Photos Contact Broker

Beneteau Oceanis 381 (Chesapeake Bay)

Price $59,000 (USD)
Location Tracy's Landing, Maryland (Chesapeake Bay)
S/V Little Wing — 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.…
64 Photos Contact Broker

Hunter 376 (Chesapeake Bay)

Price $59,000 (USD)
Location Chester, Maryland (Chesapeake Bay)
S/V Red Sky — a 1998 Hunter 376, for sale by broker.
Red Sky is a 1998 37′ Hunter 376 fractional sloop, equipped with the signature B&R rig. Designed for comfortable cruising, the Hunter 376 earned Cruising World Magazine’s “Best Value Cruiser” recognition in 1997 for combining livability, performance and equipment in a sensible package. The B&R rig on Red Sky features swept spreaders and a backstay-less geometry that produces a powerful, easily managed sail plan—well suited to short-handed or family cruising. The fractional sloop configuration promotes balanced helm feel and makes reefing and sail trim straightforward in a variety of conditions.…
77 Photos Contact Broker

Cherubini 44 (Chesapeake Bay)

Price $285,000 (USD)
Location Deltaville, VA, US (Chesapeake Bay)
S/V MAGIC — a 1986 Cherubini 44, for sale by broker.
MAGIC Meet MAGIC, likely one of the nicest Cherubini 44s on the water. While in the hands of the previous owner, MAGIC spent 10 years in a climate-controlled warehouse undergoing a major refit. The current owner purchased MAGIC in 2021 and has continued with extensive upgrades. This is a boat that wants for nothing and is ready to take her new owner to distant horizons. Vessel overview MAGIC is truly a one-of-a-kind find for the Cherubini aficionado or sailor who has a soft spot for the classics.…
77 Photos Contact Broker

Manta 40 (Chesapeake Bay)

Price $90,000 (USD)
Location Solomons, MD (Chesapeake Bay)
S/V Steal Breeze — a 1997 Manta 40, for sale by owner.

The Endeavor Manta 40 is a renowned bluewater catamaran, expertly engineered with integral keels and robust water-tight collision bulkheads to provide unmatched safety and performance at sea. Specifically designed for couples and single-handed sailors, the Manta 40 offers excellent maneuverability, a spacious layout, and practical features that make extended cruising both comfortable and efficient.

“Steal Breeze” is a well-proven example of this sought-after model, boasting over a decade of successful Caribbean cruising.…

55 Photos Contact Owner

Nauticat 40 Pilothouse (Chesapeake Bay)

Price $145,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)
S/V Aurora — a 1985 Nauticat 40 Pilothouse, for sale by broker.
Aurora is a 1985, 40′ Nauticat Pilothouse staysail ketch — a true classic bluewater yacht built to handle long passages while offering the comfortable livability required for extended cruising or full‑time liveaboard life. Nauticat Pilothouse models are well regarded for robust Scandinavian construction, a protected all‑weather helm, and seakindly, heavy‑displacement hulls that inspire confidence offshore. The pilothouse provides an elevated, sheltered steering position with excellent visibility and quick access to the interior living spaces — a practical advantage in heavy weather and a welcome feature for long‑distance voyaging.…
87 Photos Contact Broker

Gozzard 36 (Chesapeake Bay)

Price $65,000 (USD)
Location St. Leonard, Maryland (Chesapeake Bay)
Finistere — a 1988 Gozzard 36, for sale by broker.
Step aboard this timeless 1988 Gozzard 36 and discover a yacht that combines traditional elegance with practical blue-water cruising design. Her graceful clipper bow and finely crafted joinery reflect the unmistakable heritage of Ted Gozzard, designed for both beauty and purpose. At just over 42 feet long overall, she maintains a manageable footprint while offering exceptional interior volume and flexibility. Below decks, the innovative “transformer” layout adapts seamlessly to your needs, providing open social spaces or private quarters with the effortless conversion of sliding bulkheads and settees that become a comfortable centerline berth.…
23 Photos Contact Broker

Bali 4.1 (Chesapeake Bay)

Price $440,000 (USD) Reduced!
Location Annapolis, MD, US (Chesapeake Bay)
S/V Lady Ana — a 2020 Bali 4.1, for sale by broker.
Further price reduction! Now $440,000. Sellers are motivated and moving on. Come view her during the Annapolis Boat Show. Lady Ana is a thoroughly equipped, owner-version (3 cabin/3 head) Bali 4.1 in terrific condition and ready to go. The current owners (second owners) have been part-time liveaboards for three years and keep her in top shape. Recent bottom paint, wax, and polish of topsides in June 2025. Inside, the accommodation features three cabins and three baths (three stall showers), perfect for family or friends.…
172 Photos Contact Broker

Beneteau 500 Oceanis (Chesapeake Bay)

Price $110,000 (USD)
Location Norfolk, Virginia (Chesapeake Bay)
S/V Snowmane — a 1990 Beneteau 500 Oceanis, for sale by broker.
Snowmane is a 1990 Beneteau Oceanis 500 in good condition. The current and third owners cruised with their family for a year starting in Greece. In 2024 the new owners made upgrades to meet or exceed the requirements to participate in the ARC (Atlantic Rally for Cruisers), which has among the highest safety standards. They also carried out interior upgrades. Snowmane is powered by a diesel engine and has a shallow enough draft to cruise the popular spots in the Bahamas.…
67 Photos Contact Broker

Lagoon 42 Owner Version (Chesapeake Bay)

Price $418,000 (USD) Duty Paid Reduced!
Location Annapolis, MD, US (Chesapeake Bay)
S/V Reunited — a 2017 Lagoon 42 Owner Version, for sale by broker.
Privately owned, never chartered, and perfectly maintained. Maintenance records are available upon request. Duty paid, ICW mast, owner version, bluewater ready. Dockage paid through April 15, 2027. Note: TracVision domes have been removed. S/V Reunited is a meticulously maintained 2017 Lagoon 42 owner layout, offered for sale by her experienced owners, who have spared no expense for proper upkeep, preventive maintenance, and practical upgrades to enjoy comfortable cruising. She has benefited from $55,000 in recent upgrades, including a reduced mast height (ICW compliant), a new roach mainsail and stack pack, and a lithium upgrade with 1,650 Ah of batteries.…
105 Photos Contact Broker

Nautitech 395 Prestige Edition (Chesapeake Bay)

Price $160,000 (USD)
Location Cape Charles, Virginia (Chesapeake Bay)

Leopard 45 Lounge (Chesapeake Bay)

Price $779,000 (USD)
Location Annapolis, MD (Chesapeake Bay)

Leopard 50 Owners Version (Chesapeake Bay)

Price $1,125,000 (USD)
Location Annapolis, Maryland, US (Chesapeake Bay)

FP 40 ISLA (Chesapeake Bay)

Price $460,000 (USD)
Location Deltaville, VA (Chesapeake Bay)

Nonsuch 30 Ultra (Chesapeake Bay)

Price $39,000 (USD)
Location Mayo, MD (Chesapeake Bay)

Leopard 46 (Chesapeake Bay)

Price $390,000 (USD)
Location Solomons, MD (Chesapeake Bay)

Tayana 37 Cutter (Chesapeake Bay)

Price $60,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)

Hunter 336 (Chesapeake Bay)

Price $34,900 (USD)
Location Cambridge, Maryland (Chesapeake Bay)

Balance 482 (Chesapeake Bay)

Price $1,549,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)

Catalina C320 (Chesapeake Bay)

Price $40,000 (USD)
Location Deale, Maryland (Chesapeake Bay)

Lagoon 42 Owner’s Version (Chesapeake Bay)

Price $399,900 (USD)
Location Baltimore, Maryland (Chesapeake Bay)

Jeanneau 51 (Chesapeake Bay)

Price $479,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)

FP Belize 43 (Chesapeake Bay)

Price $194,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)

Scanmar 35 (Chesapeake Bay)

Price $38,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)

Pearson 35 Sloop (Chesapeake Bay)

Price $19,500 (USD)
Location Cambridge, Maryland (Chesapeake Bay)

Fountaine Pajot 41 Lipari (Chesapeake Bay)

Price $295,000 (USD)
Location Chestertown, Maryland (Chesapeake Bay)

Xquisite X5 (Chesapeake Bay)

Price $880,000 (USD)
Location Edgewater, Maryland (Chesapeake Bay)

Lagoon 380 (Chesapeake Bay)

Price $199,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)

Fountaine Pajot Saona 47 (Chesapeake Bay)

Price $739,000 (USD)
Location Mathews, VA, US (Chesapeake Bay)

Tayana 37 Cutter (Chesapeake Bay)

Price $39,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)

Leopard 48 (Chesapeake Bay)

Price $475,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)

Bali 4.1 (Chesapeake Bay)

Price $429,000 (USD)
Location Annapolis, Maryland (Chesapeake Bay)

Hylas 48 (Chesapeake Bay)

Price $1,724,571 (USD)
Location Bert Jabins Yacht Yard, Annapolis, Maryland (Chesapeake Bay)

Outremer 51 (Chesapeake Bay)

Price $1,149,000 (USD)
Location Solomons, MD, US (Chesapeake Bay)

Morgan 43 (Chesapeake Bay)

Price $59,900 (USD)
Location Pasadena, MD (Chesapeake Bay)

Leopard 46 (Chesapeake Bay)

Price $339,000 (USD)
Location EDGEWATER, MARYLAND (Chesapeake Bay)

TRT 1200 CR (Chesapeake Bay)

Price $169,000 (USD)
Location Easton, Maryland (Chesapeake Bay)

Rival 41 (Chesapeake Bay)

Price $87,500 (USD)
Location Deltaville, Virginia (Chesapeake Bay)

Arrow 1280 S (Chesapeake Bay)

Price $977,000 (USD)
Location King George, VA, US (Chesapeake Bay)

Lagoon 39 (Chesapeake Bay)

Price $285,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)

Endeavour 37 Plan A (Chesapeake Bay)

Price $37,500 (USD)
Location Norfolk, Virginia (Chesapeake Bay)

Lagoon 42 (Chesapeake Bay)

Price $499,000 (USD)
Location Norfolk, VA, US (Chesapeake Bay)

Atlantic 42 Custom (Chesapeake Bay)

Price $430,000 (USD)
Location Deltaville, VA, US (Chesapeake Bay)

Fountaine Pajot Athena 38 (Chesapeake Bay)

Price $119,000 (USD)
Location Deltaville, VA (Chesapeake Bay)

Beneteau 373 (Chesapeake Bay)

Price $89,500 (USD)
Location North Beach, Maryland (Chesapeake Bay)

Leopard 38 (Chesapeake Bay)

Price $219,000 (USD)
Location Deale, Maryland (Chesapeake Bay)

Morrelli and Melvin 46 Custom (Chesapeake Bay)

Price $299,500 (USD)
Location Hampton, VA (Chesapeake Bay)

Leopard 43 (Chesapeake Bay)

Price $250,000 (USD)
Location Galesville, Maryland (Chesapeake Bay)

Bristol 35.5 (Chesapeake Bay)

Price $69,000 (USD)
Location Annpolis, Maryland (Chesapeake Bay)

Beneteau Oceanis 381 (Chesapeake Bay)

Price $59,000 (USD)
Location Tracy's Landing, Maryland (Chesapeake Bay)

Hunter 376 (Chesapeake Bay)

Price $59,000 (USD)
Location Chester, Maryland (Chesapeake Bay)

Cherubini 44 (Chesapeake Bay)

Price $285,000 (USD)
Location Deltaville, VA, US (Chesapeake Bay)

Manta 40 (Chesapeake Bay)

Price $90,000 (USD)
Location Solomons, MD (Chesapeake Bay)

Nauticat 40 Pilothouse (Chesapeake Bay)

Price $145,000 (USD)
Location Cambridge, Maryland (Chesapeake Bay)

Gozzard 36 (Chesapeake Bay)

Price $65,000 (USD)
Location St. Leonard, Maryland (Chesapeake Bay)

Bali 4.1 (Chesapeake Bay)

Price $440,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)

Beneteau 500 Oceanis (Chesapeake Bay)

Price $110,000 (USD)
Location Norfolk, Virginia (Chesapeake Bay)

Lagoon 42 Owner Version (Chesapeake Bay)

Price $418,000 (USD)
Location Annapolis, MD, US (Chesapeake Bay)
YearPhotos and DetailsAsking PriceLocation
2000Nautitech 395 Prestige Edition$160,000 (USD)Cape Charles, Virginia
2021Leopard 45 Lounge$779,000 (USD)Annapolis, MD
2023Leopard 50 Owners Version$1,125,000 (USD)Annapolis, Maryland, US
2023FP 40 ISLA$460,000 (USD)Deltaville, VA
1987Nonsuch 30 Ultra$39,000 (USD)Mayo, MD
2008Leopard 46$390,000 (USD)Solomons, MD
1985Tayana 37 Cutter$60,000 (USD)Edgewater, Maryland
1995Hunter 336$34,900 (USD)Cambridge, Maryland
2022Balance 482$1,549,000 (USD)Annapolis, MD, US
1996Catalina C320$40,000 (USD)Deale, Maryland
2019Lagoon 42 Owner’s Version$399,900 (USD)Baltimore, Maryland
2018Jeanneau 51$479,000 (USD)Edgewater, Maryland
2000FP Belize 43$194,000 (USD)Edgewater, Maryland
1985Scanmar 35$38,000 (USD)Cambridge, Maryland
1979Pearson 35 Sloop$19,500 (USD)Cambridge, Maryland
2012Fountaine Pajot 41 Lipari$295,000 (USD)Chestertown, Maryland
2016Xquisite X5$880,000 (USD)Edgewater, Maryland
2003Lagoon 380$199,000 (USD)Annapolis, MD, US
2020Fountaine Pajot Saona 47$739,000 (USD)Mathews, VA, US
1983Tayana 37 Cutter$39,000 (USD)Cambridge, Maryland
2013Leopard 48$475,000 (USD)Annapolis, Maryland
2018Bali 4.1$429,000 (USD)Annapolis, Maryland
2027Hylas 48$1,724,571 (USD)Bert Jabins Yacht Yard, Annapolis, Maryland
2022Outremer 51$1,149,000 (USD)Solomons, MD, US
1987Morgan 43$59,900 (USD)Pasadena, MD
2007Leopard 46$339,000 (USD)EDGEWATER, MARYLAND
2002TRT 1200 CR$169,000 (USD)Easton, Maryland
1982Rival 41$87,500 (USD)Deltaville, Virginia
2026Arrow 1280 S$977,000 (USD)King George, VA, US
2014Lagoon 39$285,000 (USD)Annapolis, MD, US
1981Endeavour 37 Plan A$37,500 (USD)Norfolk, Virginia
2019Lagoon 42$499,000 (USD)Norfolk, VA, US
2003Atlantic 42 Custom$430,000 (USD)Deltaville, VA, US
1996Fountaine Pajot Athena 38$119,000 (USD)Deltaville, VA
2007Beneteau 373$89,500 (USD)North Beach, Maryland
2010Leopard 38$219,000 (USD)Deale, Maryland
2003Morrelli and Melvin 46 Custom$299,500 (USD)Hampton, VA
2006Leopard 43$250,000 (USD)Galesville, Maryland
1986Bristol 35.5$69,000 (USD)Annpolis, Maryland
1998Beneteau Oceanis 381$59,000 (USD)Tracy's Landing, Maryland
1998Hunter 376$59,000 (USD)Chester, Maryland
1986Cherubini 44$285,000 (USD)Deltaville, VA, US
1997Manta 40$90,000 (USD)Solomons, MD
1985Nauticat 40 Pilothouse$145,000 (USD)Cambridge, Maryland
1988Gozzard 36$65,000 (USD)St. Leonard, Maryland
2020Bali 4.1$440,000 (USD)Annapolis, MD, US
1990Beneteau 500 Oceanis$110,000 (USD)Norfolk, Virginia
2017Lagoon 42 Owner Version$418,000 (USD)Annapolis, MD, US