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Sailboats For Sale Maryland

20 listings found.

36 Hunter Vision 1993

Hobie Mirage Tandem Island

• Florida , United States

1972 Luders 36 by Cheoy Lee

Tartan 10 Snowballs Chance

• Connecticut

1975 Bristol 32 Sloop, Keel/CB by Ted Hood (Am’s Cup)

• Massachusetts

Used Yamaha 200 HP 4-Stroke Outboard Motor Engine

• United States

Used Yamaha 115 HP 4-Stroke Outboard Motor Engine

33ft Blue Water Sailboat

Freshwater Only – 1989 Hunter 33.5 Sloop-Rigged Cruiser, Shoal Wing Keel

F&C 44′ Ketch

Reeds Cub Scow – SOLD

Melges C Scow

470 sailboat and trailer

• Pennsylvania

1978 Hunter 30 Cheurbini

Sold – Shallow Draft Cat Ketch 24 Cruiser

1981 Pearson Flyer

Catalina 27 for sale

Hunter 44 DS perfect to live aboard!

New and Used Sailboats For Sale

Browse new and used sailboats for sale in Maryland and throughout the east coast. Annapolis is a popular destination for sailors of all sailing abilities. SailTrader exclusively offers sailboats and makes it easy to find the one your looking for in the area. View sailboat listings above or read more below on why SailTrader ii the top choice for sailors.

• Cruising Sailboats

Cruising sailboats are a popular choice for many sailors looking to get on the water with friends and family. For some sailors this means either an afternoon sail or a multi-day adventure. No matter what you’re sailing agenda is, you’re sure to find a variety cruising sailboats for sale in Maryland on SailTrader. Browse sailboats from popular cruising brands like Hunter, Catalina, Beneteau, Jenneau, Swan, Cal, Tarten, Pearson and more.

• Racing Sailboats

One Design Sailboats

One Design sailboats can often provide the best chance to learn and improve your racing skills. It’s common to find one design racing sailboats near larger bodies of water. Search sailboats for sale in Maryland from popular one design classes like the J24, J70, Tarten Ten, J105, J111, Melges 24 and more.

Dinghy’s are a often preferred due to the convenience and low maintenance costs. There are different classes that can offer a range of benefits and regattas. Browse dinghy’s for sale in Maryland like Thistles, Lightnings, Flying Scots, Scows, Optimists, 420’s, Lasers, VX Ones and more. Dinghy’s are also a popular choice in areas of Maryland that have small bodies of water. For racers, the cost of new sails for a dinghy are far less then a large racing sailboat. Search SailTrader for your next dinghy sailboat. 

Catamarans and Trimarans

Both catamarans and trimarans can be a great choice no matter if you’re a racer or cruiser. Racing multihulls are fast and light while cruising catamarans are wide and comfortable. SailTrader makes it easy to find the right catamaran or trimaran sailboat for sale in Maryland. We cater exclusively to sailors so you’ll find the latest and most recent sailboats available.

The Sailor's Choice For Sailboats For Sale in Maryland

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Sailboats for sale in Maryland

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• United States
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17 listings found

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2010 Island Packet 26 | Robert J Worton, Maryland, United States

1976 Irwin 42 | Soarsa Mayo, Maryland, United States

1981 Pearson 28 | Italica Georgetown, Maryland, United States

1979 Dufour 27 | Undaunted Edgewater, Maryland, United States

2004 Catalina 32 | One Shot Chesapeake City, Maryland, United States

1999 Amel 53 | Kristy Oxford, Maryland, United States

1996 Hanse 36.8 | Shoo Fly Pie Annapolis, Maryland, United States

1979 Seidelmann 29 | Healer North East, Maryland, United States

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1988 Performance Cruising 30 | STORYTELLER IIT Shady Side, Maryland, United States

1985 Pearson 34 Chester, Maryland, United States

1989 Ron Holland Gibbs Marine 90 | Lauren L Georgetown, Maryland, United States

1983 Tartan 30 | CocoBean Pasadena, Maryland, United States

1979 Tartan 37 | White Hawk Pasadena, Maryland, United States

1987 Island Packet 41 | shorn lamb Georgetown, Maryland, United States

1982 Cape Dory 25 | Star Rock Hall, Maryland, United States

1994 Catalina 42 | Why Not Annapolis, Maryland, United States

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Sailboats for sale in Maryland

1-15 of 156

1994 Custom Ketch Dashew Style 4JH2-HTBE

Annapolis, Maryland

Make Custom Ketch Dashew Style

Model 4JH2-HTBE

Category Sailboats

Posted Over 1 Month

1994 Custom Ketch Dashew Style 4JH2-HTBE Health concerns force another price reduction. Reasonable offers encouraged.  "Myth" fits the genre of the Dashew style of fast cruisers like the Sundeer and Deerfoot ranges. Fast cruising that allows one to outrun weather systems and shorten passage times while minimizing rolling and pitching is an enticing alternative to sailing heavy boats that have to motor in light air. Myth has a lightweight epoxy and carbon strengthened construction on a long waterline with moderate six foot draft and a manageable sailplan split between two masts that can pass under ICW bridges. The deck and hull are constructed with Tri-axial fiberglass using only epoxy resin over a Kledgicell foam core. The hull core alone provides this 24,000 pound yacht with 48,120 pounds of ultimate buoyancy. High stress areas on either side of the keel are re-inforced with carbon fiber. Flush decks, center cockpit and a hard dodger complete a design package that reeks of speed and efficiency. The  interior is well lit with white vertical surfaces and overhead. The layout features a desirable owner's aft stateroom with center-line double berth, extensive storage and an engine room that allows easy access to all sides of the motor and systems. The galley is of small apartment proportions in terms of sinks, counter space and storage. The owners of Myth sail to the Caribbean, Florida or the Bahamas each year at speed and in safety. Over the past twenty years Myth has proved herself to be the consummate passagemaker and cruising yacht for a couple. Key assets includeYanmar 75hp turboArco Solar Panels (4)SI-TEX 4KW Radar w/ touch screen (2014)WatermakerInverterRecent sails Request Information Call Now

1979 Pearson 365

Make Pearson

1979 Pearson 365 Great deal on a Pearson 365 Ketch !  This is a very sturdy boat known for its solid construction.  Recently re-powered with a new Beta 35 with only 35 hours!!! Comfortable interior with galley within easy reach of the companionway, large salon a very spacious head with separate shower. Air conditioning and heat make living aboard pleasant any time of the year. This yacht is ready to cruise with plenty of safety and navigational gear included.  Chart plotter with radar at the helm and VHF radios both down below and easy reach to the helm.  Many recent upgrades also include a new main sail, new cockpit winches and a new battery charger.    Call today to schedule your chance to see this strong, well maintained yacht first hand!

1989 Pearson 27

1989 Pearson 27 This boat is ready to help you explore the wonders of the bay while the leaves turn to a golden glow. There is no better time of year to go to new waters on the Bay, the air is cooler and water still warm. The dog days of August are archived in your past. Find those new  gunkholes!!   Extremely well kept cruiser. If you want to try out weekend cruising without breaking the bank, this is the boat for you! The Pearson 27 is a competent performance cruiser.  She offers a very easy to handle sail plan with lines leading aft to the coach roof mounted sheet stoppers, roller furling head sail and an easily reefed main.  Her cockpit features wheel steering, coaming top mounted self-tailing primary winches and a coach roof mounted mainsheet traveler.  Everything is within easy reach of the helms-person for safe, easy solo sailing.  Long bench seats, high coaming backs and flat coaming tops make her very comfortable under sail and while relaxing at anchor.  Wide side decks, inboard shrouds and coach roof mounted handrails allow easy access fore and aft for docking and anchoring.   Forward is a recessed anchor well and bow roller.    Below decks the 27 offers a very open salon with a “U” shaped dinette, cruising gallery, nav station and private aft cabin.  The salon table is mounted on the compression post and easily drops to make a comfortable double berth or raises to the ceiling to provide open seating.  The galley and nav station are opposite each other.  The nav station desk lifts to reveal a very large ice box.  Just aft of the desk is the marine head with vanity and shower.  Aft port is a private aft cabin with bi-fold door, double berth, and hanging locker.  Cushion material in super clean condition. Universal diesel engine is 10HP and fresh water cooled.

1972 MORGAN CUSTOM KETCH 47 Custom

Grasonville, Maryland

Make MORGAN CUSTOM KETCH

Model 47 Custom

1972 MORGAN CUSTOM KETCH 47 Custom This MORGAN CUSTOM KETCH 47 Will Simply Take Your Breath AwayOwned for 20+ Years By A Master Carpenter Who Has Redone Everything Including A Custom Ketch Arch That He Should PatentThe Interior Of This Vessel Is Out Of This World

1980 Pearson 424

Oxford, Maryland

1980 Pearson 424 BEL CANTO is a good cruising ketch that will take you any where you would want to go on the Bay or in the Ocean.  She has a rebuilt Yanmar 62 hp engine which is 9 hp bigger than the original.  There is room for 6 to cruise in comfort with room to spare.  The roller furling main and jib make it easy to shorten sail if weather becomes an issue.

1982 Island Trader Full Keel

Baltimore, Maryland

Make Island Trader

Model Full Keel

1982 Island Trader Full Keel, The Downtown Sailing Center, a non-profit in downtown Baltimore City is selling our Island Trader. This boat received a complete engine overhaul in 2006 and the transmission was just rebuilt in 2016. The survey in 2014 put the boat in above average condition for its year and usage.Our pricing is negotiable and we look forward to sending the boat to its new home. Please contact the DSC for more information at 410-727-0722. $42500

1994 Custom Fast Ketch Dashew Style 4JH2-HTBE

Make Custom Fast Ketch Dashew Style

1994 Custom Fast Ketch Dashew Style 4JH2-HTBE   Designed and built by David Mix, "Myth" fits the genre of the Dashew style of fast cruisers like the Sundeer and Deerfoot ranges. Fast cruising that allows one to outrun weather systems and shorten passage times while minimizing rolling and pitching is an enticing alternative to sailing heavy boats that have to motor in light air. Myth's has a lightweight epoxy and carbon strengthened construction on a long waterline with moderate six foot draft and a manageable sailplan split between two masts that can pass under ICW bridges. The deck and hull are constructed with Tri-axial fiberglass using only epoxy resin over a Kledgicell foam core. High stress areas on either side of the keel are re-inforced with carbon fiber. Flush decks, center cockpit and a hard dodger complete a design package that reeks of speed and efficiency. The  interior is well lit with white vertical surfaces and overhead. The layout features a desirable owner's aft stateroom with centerline double berth, extensive storage and an engine room that allows easy access to all sides of the motor and systems. The galley is of small apartment proportions in terms of sinks, counter space and storage. The owners of Myth sail to the Caribbean, Florida or the Bahamas each year at speed and in safety. Over the past twenty years Myth has proved herself to be the consummate passagemaker and cruising yacht for a couple. Key assets includeYanmar 75hp turboArco Solar Panels (4)SI-TEX 4KW Radar w/ touch screen (2014)WatermakerInverterNew sails New radarProfurl headsail furlerMonitor Wind Vane steering

2006 Hunter 45 Center Cockpit

Make Hunter

Model 45 Center Cockpit

2006 Hunter 45 Center Cockpit Preliminary listing, subject to owners approval A very well cared for and low hour example of the very popular Hunter 45 Center- Cockpit.  This particular boat is loaded with equipment to make cruising a breeze -Excellent Raymarine electronics packageGeneratorInverterHigh output alternatorDual zone air-conditioningCockpit enclosure Dinghy davitsJust 320 hours on main engine!Much more, please see full spec tab The owners have taken excellent care of the boat seasonally and the overall condition truly shows.  We don't anticipate this boat to last long, so please call now.

1995 Hunter 37.5

1995 Hunter 37.5 "Genesis" is a well equipped performance cruiser that has excellent accommodations below and a comfortable cockpit that allows for easy sailing underway and a great place to entertain guests at the dock or swinging on the hook. Features include:Reverse cycle air conditioningDodger, bimini, and connectorRefrigerator and freezerExcellent electronics including radar

1981 Island Packet 26 Mark I

Make Island Packet

Model 26 Mark I

1981 Island Packet 26 Mark I New Listing With Specs And Pics To Follow

2006 Alerion Express 28

Make Alerion

Model Express 28

2006 Alerion Express 28 'The prettiest girl at the ball'.  It's hard to take one's eyes off the stunning lines of the Alerion 28 Express.  Pleiades III has a dark green hull which adds to her allure. With large cockpit, easy to handle rigging and long tiller, the Alerion 28 is easy and fun to sail.  The cuddy cabin can sleep up to 3 if necessary and Pleiades has a basin and head.  This Carl Schumacher design, is a quality yacht produced by Pearson Composites, utilizing the SCRIMP system of resin infusion by vacuum.  The AE 28  performs superbly under sail, and is designed to be sailed single handed. With a fin keel and spade rudder the boat is exceptionally maneuverable and stable.  The Hoyt Jib Boom is self-tacking and takes the anxiety out of the tack with the mainsail easily managed from the seated position at the tiller. The boat is beautifully balanced under sail. The 14-hp Yanmar diesel with sail-drive is a reliable means of getting into and out of the slip - that's all its needed for as the Alerions just want to sail all the time!

2011 Beneteau 3YM30

Make Beneteau

Model 3YM30

2011 Beneteau 3YM30 "BLUE HERON" is the very popular two cabin, one head model; making her perfect for a couple or a young family. She is a great example of what the BENETEAU 34 has to offer. She is rigged for easy sailing with all the lines leading into the cockpit. Offering dockside A/C and HEAT, she is very comfortable for cruising. There are very few Beneteau 34's on the market quite like "BLUE HERON".DOCKSIDE AC/HEATBIMINI AND DODGER WITH GRAB RAILS ROLLER FURLING MAIN WITH BATTENSWINDLESS

1995 Beneteau 281

1995 Beneteau 281 The Oceanis 281 is a perfect pocket cruiser. Compact and able to go places that any big boat can go and many places that big boats can't!Afterglow has a large aft cabin, galley, head with shower, salon, chart table and open v-berth. Easy access from the water, via a swim platform and walk-through transom into a comfortable cockpit. Upgrades include:Raymarine ST4000+ Autopilot (2004) integrated with aGarmin GPSMap 478  (2008)Adler Barbour 12V refrigerationFull bimini (2012)New Sails  in 2012Asymmetrical SpinnakerPolyplanar Stereo w/ iPod docking station (2012) & Bose speakers & cockpit speakers. Don't miss out on this comfy cruiser.

2016 Lagoon 52

Request Price

Make Lagoon

2016 Lagoon 52 The Lagoon 52 marks a whole new era in the design of this class of boats. She is an extraordinary catamaran expressing elegance, comfort, safety, user friendliness, and performance under sail. With its diamond-shaped vertical bows, beveled hulls, and tall rig, the Lagoon 52 is no ordinary catamaran, but its originality goes a great deal further than just its "outer" appearance, or even its interior layout. The continuous horizontal and fluent lines give the interior open and generous spaces, along with a continuity between exterior and interior life. The Lagoon 52 is graceful in style and symmetry while exuding a sense of well-being and opulence. PLEASE CONTACT US FOR DETAILS ON THE 52ST IN THE 2016 MIAMI BOAT SHOW!

2016 Lagoon 39

2016 Lagoon 39 The Lagoon 39 has proven her strength in character with her vertical, beveled bows and aft center mast for sailing performance and ease of handling.  Comfort and safety is a central theme of the Lagoon 39. She offers a simple, efficient deck layout, giving you the ability to control the main from the steering station, and for an easy and protected boarding. The cockpit is well protected and comfortable, with a wide crossing passage aft, a dining table to port, a settee to starboard, and direct access to the steering station from the cockpit AND from the deck. The inventive and elegant interior is drenched in natural light and provides ventilation throughout. There's a wide choice of layouts including 2, 3 or 4 cabins. PLEASE CONTACT US FOR DETAILS ON THE 2016 MIAMI BOAT SHOW LAGOON 39,

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You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

Top destinations for sailboat rentals

Top sailboat rentals reviews in Maryland

Cruise the...

Sailing on Andromeda with Capt Brian was a wonderful experience for my family and me. The boat was clean, spacious &...

Excellent...

Great day out on the Windsnap. The boat was in excellent working condition and ready to sail. She was a lot of fun to...

Great experience once again. Plan to rent in the future.

Jonathan’s boat is well-kept. He provides handy instructions and communicates promptly. Highly recommend renting with...

LANI - Leopard...

We had a great time on the water despite weak winds. Jonathan keeps the Windsnap in very good condition and was...

Hands down great boat and great Captain

The boat was terrific. I would highly recommend renting this boat.

ESCAPE--Leopard...

My party and I had an awesome time! The original boat we booked was having trouble and Cap Shawn accommodated us with...

had the best time!! The captain was amazing, the group had so much fun. Would definitely do it again and 100%...

Jonathan was very thorough at letting us know exactly what to expect as far as getting everything up and running....

Sailboat Rentals in Maryland

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