Sailboats For Sale in Chesapeake Bay

( 71 Results )

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.…
25 Photos Contact Broker

Beneteau Oceanis 41 (Chesapeake Bay)

Asking $185,000 (USD)
Location DELTAVILLE, Virginia (Chesapeake Bay)
S/V Breeze is a 2014 Beneteau Oceanis 41 for sale by broker.
Breeze is a two-cabin, one-head Beneteau Oceanis 41. This model was the first of the new generation of hard-chine boats of the time, designed to sail fast and settle to the chine, as well as increase interior volume. The beam is carried aft, creating a large cockpit with excellent storage. The full-beam, fold-down transom was one of the most desirable features of the boat—the first of its kind, soon mimicked by other manufacturers. When at anchor it creates a long swim platform and allows easy access from the water into the cockpit.…
57 Photos Contact Broker

Lagoon 42 Owner’s Version (Chesapeake Bay)

Asking $449,000 (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.…
61 Photos Contact Broker

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 Contact Broker

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 Contact Broker

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 Contact Broker

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.…
54 Photos Contact Broker

Hunter 410 (Chesapeake Bay)

Asking $89,900 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Dream Catcher is a 1998 Hunter 410 for sale by broker.
Dream Catcher is a lovingly maintained example of the popular Hunter 410. Her comfortable interior boasts a spacious 2-cabin, 2-head layout, with a desirable separate shower in the aft head. Solar, davits, and an easy-to-handle furling mainsail and headsail make this boat a dream to sail and cruise. Reverse-cycle air conditioning is a welcome luxury for those warm Chesapeake Bay summer months. Or, take advantage of the Hunter 410’s cruising prowess and just go somewhere with better weather. Don’t let this dream slip away!…
32 Photos Contact Broker

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.…
24 Photos Contact Broker

Catalina 355 (Chesapeake Bay)

Asking $219,500 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Tiger Lily is a 2017 Catalina 355 for sale by broker.
Living the dream in comfort! The Catalina 355 is an extremely popular model which gives the feel of a much larger boat. The high freeboard and wide beam create expansive interior volume for this 2-cabin 1-head boat. The spacious cockpit, wide side decks, walk-through transom allow for ease of movement throughout the vessel, with all sail handling from the cockpit. The interior is light and well appointed; the flexibility in the salon layout creates options for added guests if necessary. The port settee can convert to a 2-seat/cocktail table arrangement, while the dining table has leaves that fold out to form a full-size table and drops down to form a double berth.…
37 Photos Contact Broker

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.…
45 Photos Contact Broker

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.…
61 Photos Contact Broker

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.…
97 Photos Contact Broker

Jeanneau 440 (Chesapeake Bay)

Asking $399,000 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Cinnamon Girl is a 2022 Jeanneau 440 for sale by broker.
If you are looking for ‘similar, but very different’, take a look at Cinnamon Girl. Her owners thought long and hard about how they planned to use the boat; they wanted totally self-sufficient, low-energy, off-grid cruising capabilities and outfitted this Jeanneau Sun Odyssey 440 accordingly. Consequently, this is a unique version of this model. The Sun Odyssey 440 is renowned for its comfortable accommodations, both on deck and down below. The hard chine creates a good sailing hull with fine lines at the waterline and allows for expanded interior volume.…
69 Photos Contact Broker

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.…
58 Photos Contact Broker

Leopard 48 (Chesapeake Bay)

Asking $489,000 (USD)
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.…
94 Photos Contact Broker

Beneteau Oceanis 473 (Chesapeake Bay)

Asking $159,000 (USD)
Location Urbanna, Virginia (Chesapeake Bay)
S/V Brer Fox is a 2003 Beneteau Oceanis 473 for sale by broker.
Looking for a family cruiser that will sail well and ‘play’ well? Look no further than Brer Fox, a three-cabin, two-head version of the very popular Beneteau 473. She is in the water in Urbanna, Virginia. She has largely sailed the Chesapeake Bay, so has seen relatively light use. As one of the last ‘old school’ Beneteaus with a cherry interior and a traditional interior feel, the 473 is renowned for its sailing ability, sea-kindliness, and superb liveability. The interior is spacious and light.…
56 Photos Contact Broker

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.…
23 Photos Contact Broker

Jeanneau 349 (Chesapeake Bay)

Asking $135,000 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Magic is a 2015 Jeanneau 349 for sale by broker.
Sailing fun – cruising comfort! The Jeanneau 349 is built for coastal and Bahamas cruising in style and comfort. The fin keel with bulb keeps the weight low, and twin rudders reduce drag, making for fast, fun sailing. The hard chines create interior volume while maintaining waterline length. It is a fabulous platform on which the current owner has built terrific cruising capabilities with major upgrades in 2024 and 2025. The owners used the boat actively until the fall of 2025.…
57 Photos Contact Broker

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 Contact Owner

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.…
29 Photos Contact Broker

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.…
56 Photos Contact Broker

Beneteau 48 (Chesapeake Bay)

Asking $299,500 (USD)
Location Hampton, Virginia (Chesapeake Bay)
S/V Pleiades is a 2016 Beneteau 48 for sale by broker.
SUMMER SOLSTICE PRICE ADJUSTMENT! This 3-cabin, 2-head Beneteau Oceanis 48 is in the water in Hampton, VA. Pleiades is lightly used and has only been sailed on the Chesapeake Bay, but this is an ocean-going vessel, strong, sea-worthy and sea-kindly with phenomenal sailing characteristics and copious accommodations. The Oceanis 48 was designed for maximum performance and maximum comfort. The beam is carried all the way aft with a hard chine which allows the boat to heel to the chine and then track beautifully, getting ‘into the groove’ with speed and comfort.…
62 Photos Contact Broker

TRT 1200 CR (Chesapeake Bay)

Asking $185,000 (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.…
41 Photos Contact Owner

Beneteau 54 Oceanis (Chesapeake Bay)

Asking $796,000 (USD)
Location Hampton, Virginia (Chesapeake Bay)
S/V Circe is a 2022 Beneteau 54 Oceanis Yacht for sale by broker.
JULY ’26 – $53 000 PRICE IMPROVEMENT. Circe is a magnificent vessel with the best of credentials – luxurious live aboard and sublime sailing. The Oceanis Yacht is the most recent example of Beneteau innovation leading the way, to create a fast, luxurious cruising boat. Based on the hull design of the First 53, the designers have maximized performance, along with maneuverability on deck, by creating a flush deck ‘center cockpit’ style vessel with wide side decks that push all the way to the stern and an open aft deck behind the helms.…
77 Photos Contact Broker

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.…
106 Photos Contact Broker

Beneteau 331 (Chesapeake Bay)

Asking $49,900 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Hakuna Matata is a 2003 Beneteau 331 for sale by broker.
Hakuna Matata is a lovingly maintained example of the popular Beneteau 331. Her comfortable interior boasts a spacious two-cabin, one-head layout, with a desirable separate shower. Solar, davits, and an easy-to-handle furling mainsail and headsail make this boat a dream to sail and cruise. Reverse-cycle air conditioning is a welcome luxury for those warm Chesapeake Bay summer months. Hakuna Matata ain’t no passin’ craze, so make her your problem-free philosophy! Contact Matt Lambert with YaZu Yachting regarding co-brokerage opportunities.…
25 Photos Contact Broker

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 Contact Broker

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.…
34 Photos Contact Broker

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 Contact Broker

Fountaine Pajot 47 Tanna (Chesapeake Bay)

Asking $899,000 (USD) Duty Paid
Location Annapolis, Maryland, US (Chesapeake Bay)
S/V Lucky Dog is a 2022 Fountaine Pajot Tanna 47 for sale by broker.
2022 Fountaine Pajot Tanna 47 – 3 Cabin Owners version – Highly Upgraded, Offshore-Ready and US tax paid. Meet Lucky Dog – The most aggressively priced Tax Paid Tanna 47 to ever hit the US market. (Never chartered) She stands out as one of the most comprehensively upgraded and intelligently outfitted examples of the model available today. Built for true blue-water cruising and luxurious liveaboard comfort, she blends factory options with an exceptional suite of custom enhancements—delivering performance, redundancy and self-sufficiency.…
113 Photos Contact Broker

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 Contact Broker

Mason 43 (Chesapeake Bay)

Asking $79,900 (USD)
Location Gloucester Point, Virginia (Chesapeake Bay)
S/V Outrageous is a 1981 Mason 43 for sale by broker.
Outrageous is a beautiful, well-maintained example of the classic Mason 43 cruiser and is well outfitted and ready to be sailed wherever her new owner wishes to go. This boat offers two cabins with multiple berthing options and one head featuring a sizable separate shower. Her Perkins 4-108 inboard diesel has less than 200 hours since it was rebuilt. A safe, spacious cockpit, as well as plenty of open deck space, allow for comfort and relaxation above decks. Below decks, Outrageous shines with beautiful woodwork and the feel of a comfortable sailing yacht.…
34 Photos Contact Broker

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.…
132 Photos Contact Broker

Lagoon 420 (Chesapeake Bay)

Asking $310,000 (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.…
61 Photos Contact Broker

Beneteau 46.1 (Chesapeake Bay)

Asking $448,732 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Fat Bottom Girl is a 2020 Beneteau 46.1 for sale by broker.
The Beneteau Oceanis 46.1 is a luxurious vessel with excellent sailing credentials thanks to the fine bow, long waterline and “flat” underwater shape of hull. The hard chine creates vast interior volume above the waterline and on the Oceanis 46.1 the beam is carried aft to create an enormous cockpit which is comfortable under sail and has space for numerous guests and crew members. The full-width, fold-down transom and dual helms allow seamless flow to and from the water, a plus for cruisers.…
79 Photos Contact Broker

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.…
85 Photos Contact Broker

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.…
41 Photos Contact Owner

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.…
56 Photos Contact Broker

Beneteau 38s5 (Chesapeake Bay)

Asking $40,000 (USD)
Location St. Michaels, Maryland (Chesapeake Bay)
S/V Carpe Diem is a 1992 Beneteau 38s5 First for sale by broker.
Carpe Diem is a 1992 38′ Beneteau First 38s5, a compact performance-cruiser that blends sailing capability with comfortable accommodations. The boat features a two‑stateroom, two‑head layout that provides private sleeping quarters fore and aft and practical separation of accommodations for extended cruising or when hosting guests. Belowdecks the interior is arranged for efficient liveaboard use: a functional galley and navigation station, a bright saloon with good headroom and seating, and dedicated storage spaces distributed throughout the vessel. The two heads add an important level of convenience for family cruising or passagemaking, and the layout supports both short cruises and longer trips in comfort.…
55 Photos Contact Broker

Beneteau 373 (Chesapeake Bay)

Asking $95,000 (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.…
73 Photos Contact Broker

Montevideo 43 (Chesapeake Bay)

Asking $72,500 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Calypso is a 1993 Med Marine Montevideo for sale by broker.
This sturdy South African-built, Fred Scholtz–designed, center-cockpit cruising vessel has proven her worth with a circumnavigation (2004–2017) under her keel. Calypso has several years cruising the coast of Southern Africa and the current owner left the shores of South Africa for the Caribbean and the east coast of the USA in early 2022. She was hauled in September 2025, after a summer in the Northeast. The fine bow, 6’6″ draft, tall rig, encapsulated keel, and center cockpit make the Montevideo a fast, safe cruising vessel.…
75 Photos Contact Broker

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.…
42 Photos Contact Broker

Corsair F-24 MkII (Chesapeake Bay)

Asking $24,900 (USD)
Location Deltaville, Virginia (Chesapeake Bay)
S/V Little My is a 1999 Corsair F-24 MkII for sale by broker.
Little My is a clean and well-maintained example of the Corsair 24 MkII trimaran. She has made her current owners and family happy since 2012, and now this is your opportunity to have a lightning-fast coastal racer/cruiser that won’t be limited when it comes to exploring the shallows. Her interior layout also makes this a wonderful option as a gunkhole cruiser with sleeping berths for two adults and two children, as well as a plumbed marine head. New standing rigging as of 2022 and diligent maintenance by the current owner make this Corsair 24 MkII an awesome turnkey boat.…
21 Photos Contact Broker

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.…

33 Photos Contact Owner

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.…
35 Photos Contact Owner

Bristol 35.5 (Chesapeake Bay)

Asking $80,000 (USD)
Location Annpolis, Maryland (Chesapeake Bay)
S/V Skye is a 1986 Bristol 35.5C for sale by broker.
Skye is a 1986 Bristol 35.5C, a 35′ center-cockpit cruising yacht presented in very nice condition. This example reflects the solid build quality and thoughtful layout that made the Bristol 35.5C a popular choice for couples and small crews seeking a comfortable offshore-capable boat. The Bristol 35.5C center-cockpit configuration provides a protected helm and a private aft cabin, yielding a comfortable interior arrangement with a roomy saloon, practical galley and a separate head — a layout well suited to extended cruising.…
67 Photos Contact Broker

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.…
64 Photos Contact Broker

Catalina C320 (Chesapeake Bay)

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

Beneteau Oceanis 41 (Chesapeake Bay)

$185,000 (USD)
DELTAVILLE, Virginia (Chesapeake Bay)

Lagoon 42 Owner’s Version (Chesapeake Bay)

$449,000 (USD) Duty Paid
Baltimore, Maryland (Chesapeake Bay)

Jeanneau 51 (Chesapeake Bay)

$499,000 (USD)
Edgewater, Maryland (Chesapeake Bay)

FP Belize 43 (Chesapeake Bay)

$199,000 (USD)
Edgewater, Maryland (Chesapeake Bay)

Scanmar 35 (Chesapeake Bay)

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

Pearson 35 Sloop (Chesapeake Bay)

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

Hunter 410 (Chesapeake Bay)

$89,900 (USD)
Deltaville, Virginia (Chesapeake Bay)

Fountaine Pajot 41 Lipari (Chesapeake Bay)

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

Catalina 355 (Chesapeake Bay)

$219,500 (USD)
Deltaville, Virginia (Chesapeake Bay)

Xquisite X5 (Chesapeake Bay)

$890,000 (USD) Duty Paid
Edgewater, Maryland (Chesapeake Bay)

Lagoon 380 (Chesapeake Bay)

$219,000 (USD)
Annapolis, MD, US (Chesapeake Bay)

Fountaine Pajot Saona 47 (Chesapeake Bay)

$765,000 (USD)
Mathews, VA, US (Chesapeake Bay)

Jeanneau 440 (Chesapeake Bay)

$399,000 (USD)
Deltaville, Virginia (Chesapeake Bay)

Tayana 37 Cutter (Chesapeake Bay)

$45,000 (USD)
Cambridge, Maryland (Chesapeake Bay)

Leopard 48 (Chesapeake Bay)

$489,000 (USD)
Annapolis, Maryland (Chesapeake Bay)

Beneteau Oceanis 473 (Chesapeake Bay)

$159,000 (USD)
Urbanna, Virginia (Chesapeake Bay)

Bali 4.1 (Chesapeake Bay)

$440,000 (USD)
Annapolis, Maryland (Chesapeake Bay)

Jeanneau 349 (Chesapeake Bay)

$135,000 (USD)
Deltaville, Virginia (Chesapeake Bay)

Leopard 42 (Chesapeake Bay)

$157,777 (USD) Duty Paid
Hayes, VA (Chesapeake Bay)

Morgan 43 (Chesapeake Bay)

$64,900 (USD)
Pasadena, MD (Chesapeake Bay)

Leopard 46 (Chesapeake Bay)

$349,000 (USD)
EDGEWATER, MARYLAND (Chesapeake Bay)

Beneteau 48 (Chesapeake Bay)

$299,500 (USD)
Hampton, Virginia (Chesapeake Bay)

TRT 1200 CR (Chesapeake Bay)

$185,000 (USD) Duty Paid
Easton, Maryland (Chesapeake Bay)

Beneteau 54 Oceanis (Chesapeake Bay)

$796,000 (USD)
Hampton, Virginia (Chesapeake Bay)

Rival 41 (Chesapeake Bay)

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

Beneteau 331 (Chesapeake Bay)

$49,900 (USD)
Deltaville, Virginia (Chesapeake Bay)

Arrow 1280 S (Chesapeake Bay)

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

Lagoon 39 (Chesapeake Bay)

$299,000 (USD) Duty Paid
Annapolis, MD, US (Chesapeake Bay)

Endeavour 37 Plan A (Chesapeake Bay)

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

Fountaine Pajot 47 Tanna (Chesapeake Bay)

$899,000 (USD) Duty Paid
Annapolis, Maryland, US (Chesapeake Bay)

Fountaine Pajot FP Isla 40 (Chesapeake Bay)

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

Mason 43 (Chesapeake Bay)

$79,900 (USD)
Gloucester Point, Virginia (Chesapeake Bay)

Lagoon 42 (Chesapeake Bay)

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

Lagoon 420 (Chesapeake Bay)

$310,000 (USD)
Edgewater, Maryland (Chesapeake Bay)

Beneteau 46.1 (Chesapeake Bay)

$448,732 (USD)
Deltaville, Virginia (Chesapeake Bay)

Atlantic 42 Custom (Chesapeake Bay)

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

Fountaine Pajot Athena 38 (Chesapeake Bay)

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

S2 C36 (Chesapeake Bay)

$26,750 (USD)
St. Michaels, Maryland (Chesapeake Bay)

Beneteau 38s5 (Chesapeake Bay)

$40,000 (USD)
St. Michaels, Maryland (Chesapeake Bay)

Beneteau 373 (Chesapeake Bay)

$95,000 (USD)
North Beach, Maryland (Chesapeake Bay)

Montevideo 43 (Chesapeake Bay)

$72,500 (USD)
Deltaville, Virginia (Chesapeake Bay)

Leopard 38 (Chesapeake Bay)

$219,000 (USD) Duty Paid
Deale, Maryland (Chesapeake Bay)

Corsair F-24 MkII (Chesapeake Bay)

$24,900 (USD)
Deltaville, Virginia (Chesapeake Bay)

Morrelli and Melvin 46 Custom (Chesapeake Bay)

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

Leopard 43 (Chesapeake Bay)

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

Bristol 35.5 (Chesapeake Bay)

$80,000 (USD)
Annpolis, Maryland (Chesapeake Bay)

Beneteau Oceanis 381 (Chesapeake Bay)

$59,000 (USD)
Tracy's Landing, Maryland (Chesapeake Bay)
YearPhotos and DetailsAsking PriceLocation
1996Catalina C320$40,000 (USD)Deale, Maryland
2014Beneteau Oceanis 41$185,000 (USD)DELTAVILLE, Virginia
2019Lagoon 42 Owner’s Version$449,000 (USD)Baltimore, Maryland
2018Jeanneau 51$499,000 (USD)Edgewater, Maryland
2000FP Belize 43$199,000 (USD)Edgewater, Maryland
1985Scanmar 35$38,000 (USD)Cambridge, Maryland
1979Pearson 35 Sloop$19,500 (USD)Cambridge, Maryland
1998Hunter 410$89,900 (USD)Deltaville, Virginia
2012Fountaine Pajot 41 Lipari$295,000 (USD)Chestertown, Maryland
2017Catalina 355$219,500 (USD)Deltaville, Virginia
2016Xquisite X5$890,000 (USD)Edgewater, Maryland
2003Lagoon 380$219,000 (USD)Annapolis, MD, US
2020Fountaine Pajot Saona 47$765,000 (USD)Mathews, VA, US
2022Jeanneau 440$399,000 (USD)Deltaville, Virginia
1983Tayana 37 Cutter$45,000 (USD)Cambridge, Maryland
2013Leopard 48$489,000 (USD)Annapolis, Maryland
2003Beneteau Oceanis 473$159,000 (USD)Urbanna, Virginia
2018Bali 4.1$440,000 (USD)Annapolis, Maryland
2015Jeanneau 349$135,000 (USD)Deltaville, Virginia
2003Leopard 42$157,777 (USD)Hayes, VA
1987Morgan 43$64,900 (USD)Pasadena, MD
2007Leopard 46$349,000 (USD)EDGEWATER, MARYLAND
2016Beneteau 48$299,500 (USD)Hampton, Virginia
2002TRT 1200 CR$185,000 (USD)Easton, Maryland
2022Beneteau 54 Oceanis$796,000 (USD)Hampton, Virginia
1982Rival 41$87,500 (USD)Deltaville, Virginia
2003Beneteau 331$49,900 (USD)Deltaville, Virginia
2026Arrow 1280 S$977,000 (USD)King George, VA, US
2014Lagoon 39$299,000 (USD)Annapolis, MD, US
1981Endeavour 37 Plan A$37,500 (USD)Norfolk, Virginia
2022Fountaine Pajot 47 Tanna$899,000 (USD)Annapolis, Maryland, US
2023Fountaine Pajot FP Isla 40$479,000 (USD)Edgewater, Maryland
1981Mason 43$79,900 (USD)Gloucester Point, Virginia
2019Lagoon 42$499,000 (USD)Norfolk, VA, US
2008Lagoon 420$310,000 (USD)Edgewater, Maryland
2020Beneteau 46.1$448,732 (USD)Deltaville, Virginia
2003Atlantic 42 Custom$430,000 (USD)Deltaville, VA, US
1996Fountaine Pajot Athena 38$119,000 (USD)Deltaville, VA
1981S2 C36$26,750 (USD)St. Michaels, Maryland
1992Beneteau 38s5$40,000 (USD)St. Michaels, Maryland
2007Beneteau 373$95,000 (USD)North Beach, Maryland
1993Montevideo 43$72,500 (USD)Deltaville, Virginia
2010Leopard 38$219,000 (USD)Deale, Maryland
1999Corsair F-24 MkII$24,900 (USD)Deltaville, Virginia
2003Morrelli and Melvin 46 Custom$299,500 (USD)Hampton, VA
2006Leopard 43$250,000 (USD)Galesville, Maryland
1986Bristol 35.5$80,000 (USD)Annpolis, Maryland
1998Beneteau Oceanis 381$59,000 (USD)Tracy's Landing, Maryland