Cruising Sailboats for sale in Maryland

105 New and Used Cruising Sailboats

Moody 36

Cape Saint Claire... (United States of America)

35.99 ft.

1979

Used

1979 MOODY SAILBOAT 36 BILL DIXON DESIGN.READY TO SET SAIL Do you want to cruise the World? Hop around the Caribbean? Check out this 1979 Moody 36 center cockpit, c...

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$23,000

Marlow Hunter Hunter 37 Legend

Crownsville, Mary... (United States of America)

37.01 ft.

1988

Used

Legend 37 with many improvements, solar panel, Garmin 700 chartplotter, propane conversion! The Hunter 37 is a stable and dependable sailing boat that is made to tr...

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$27,000

Jeanneau 349

Annapolis, Maryland (United States of America)

33.99 ft.

2023

Used

MORE INFO Manufacture Installed Options SUN ODYSSEY 349 YANMAR 21HP (3YM20) SHAFT DRIVE SHOAL DRAFT IRON KEEL 2 CABINS / 1 HEAD VERSION - TEAK 1 forward c...

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$229,000

Ericson 27

Baltimore, Maryland (United States of America)

27.0 ft.

1977

Used

Beautiful Classic Ericson with trailer and major interior refit Clean Sailboat!! Come take a look!! A great sailboat for a weekend cruise around the bay. This 1977...

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$19,900

Tartan 37

Oxford, Maryland (United States of America)

37.01 ft.

1984

Used

Accommodations The Tartan 37 is one of the best received Tartans ever built. Designed by Sparkman and Stephens. They are known for their excellent sailing ability ...

$59,000

Beneteau First 42

Annapolis, Maryland (United States of America)

41.99 ft.

1981

Used

MORE INFO PRICE REDUCED 8/7/2024. THE OWNERS WANT THIS BOAT SOLD! Some of CHARDONNAY's highlights: 2013 Volvo D2-55 diesel and transmission with under 400...

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$59,900

Najad Aphrodite 42

Annapolis, Maryland (United States of America)

41.99 ft.

1989

Used

FULL SPECS Comfort: - interior custom carpet, for entire flooring. Teak floors throughout - fridge and freezer unit, Frigoboat 12 Volt - windlass with remote cont...

$169,000

Sabre 32

Tracys Landing, M... (United States of America)

32.15 ft.

1984

Used

SPARROW is an exceptional example of a Sabre 32 and we believe in the best condition on the market today. Hull #3 features the rare Tri cabin version giving her addit...

$25,000

J Boats J35

Annapolis , Maryland (United States of America)

35.43 ft.

1986

Used

Hull Type: Fin w/spade rudder Rigging Type: Masthead Sloop LOA: 35.50 ft / 10.82 m LWL: 30.00 ft / 9.14 m S.A. (reported): 636.00 ft² / 59.09 m² Beam: 11.80 ft /...

$22,500

Sabre 38 Mk I

Baltimore, Maryland (United States of America)

37.99 ft.

1985

Used

Excellent Cruiser. Many updated features. Ready for the next adventure. This Sabre 38 Mark I has a great layout for cruising with guests or living aboard. She has t...

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$26,900

Bruce Roberts 43

Annapolis, Maryland (United States of America)

43.01 ft.

1998

Used

$49,000

Nebe Shearwater 39

Deale, Maryland (United States of America)

43.01 ft.

1995

Used

$10K PRICE DROP 04/14 Dimensions Name...............................................................Bagheera Year....................................................

$92,950

Beneteau

Tracys Landing, MD (United States of America)

50.0 ft.

1993

Used

51' Beneteau 1993 This Beneteau has four cabins, four heads and a separate crew cabin. She is perfect for long trips to the Islands or to take you and a crew arou...

$89,900

Pacific Seacraft 31

Annapolis, Maryland (United States of America)

31.0 ft.

2004

Used

MORE INFO JUST LISTED IN ANNAPOLIS -- $80,000 in UPGRADES (Preliminary Info - Additional Details and Photos to be Posted Soon) ** Cutter rig -w/twin furlers...

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$150,000

Beneteau Oceanis 49

Solomons, Maryland (United States of America)

49.02 ft.

2008

Used

MORE INFO RECENT UPDATES & SPECIAL FEATURES OVER $130,000 SPENT OVER THE LAST YEAR PREPPING TOPAZ FOR A TRIP TO THE ISLANDS AND MEDITERRANEAN! Spacious 3-...

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$279,900

Marlow Hunter Hunter 40

Pasadena, Maryland (United States of America)

39.99 ft.

1985

Used

FULL SPECS Newer lights and cushions Rebuilt transmission, engine injector pump, and oil cooler, new clamps and gaskets New fuel fill and vent hoses New electrica...

$19,900

Marlow Hunter Hunter 33

North Beach, Mary... (United States of America)

33.5 ft.

2012

Used

Full Description Cockpit Steering Console Engine Control, Wheel Brake, Lighted Compass, Space for Instruments, & Stainless Steel Wheel Guard Lewmar Folding ...

$79,950

Pacific Seacraft 37

Annapolis, Maryland (United States of America)

37.01 ft.

1995

Used

MORE INFO ** NEW TO THE MARKET ** NOW REDUCED ** -EXTENSIVE OFFSHORE UPGRADES- -Additional Photos and Info Posted Recently - with more to follow- * Proven...

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$125,000

Pearson 35

Fort Washington, ... (United States of America)

35.01 ft.

1981

Used

1981 Pearson 35 Bill Shaw Monoinjection hull ready for new home! You have been asking for this 1981 Pearson 35 and it has finally arrived. If you are handy and read...

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$21,750

Catalina 30

Solomons, Maryland (United States of America)

29.99 ft.

1988

Used

Accommodations The Catalina 30 is known for their expansive space for a 30 footer. Ecphora has been very well maintained and loved by her present owners for over 20 ...

$18,000

Catalina 380

Cambridge, Maryland (United States of America)

37.99 ft.

1996

Used

Ruste Nayle has had basically 2 owners as the first owner only had her about a year. The next two owners have been very pro-active to continually upgrade the vessel w...

$78,500

Beneteau Oceanis 381

Crownsville, Mary... (United States of America)

38.58 ft.

1998

Used

Layout & Accommodations Two cabin with double berths and two heads.Salon table can be expanded and dropped down to form another berth. Galley Two burner ...

$77,000

Pacific Seacraft

Annapolis, Maryland (United States of America)

37.01 ft.

2000

Used

MORE INFO R E D U C E D !! ** $150K in Recent Upgrades/Refit!! ** Rugged Pacific Seacraft Construction -- Seakindly Crealock Design Inducted into the Sai...

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$185,000

Tartan 395

Annapolis, Maryland (United States of America)

39.01 ft.

2024

New

MORE INFO TARTAN 395 # 14 MSRP COMPLETE - $632,555 SPECIAL PRICE - $570,000 SAVINGS - $64,555 New Tartan 395 Hull #Model Year! In Stock at our Annapol...

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$570,000

Passport 40

Tracy Landing, Ma... (United States of America)

39.34 ft.

1982

Used

Enter the beautifully appointed interior of the Passport 40 and immerse yourself in the warmth of fine craftsmanship. The rich teak finishes create an inviting and co...

$82,950

Beneteau First 32.5

North Beach, Mary... (United States of America)

32.51 ft.

1989

Used

Racer-cruiser style boat, perfect for beer-can racing on weeknights here in Annapolis. Owner says one of the best assets is the ability to sail well in light air (any...

$24,900

Islander 36

Chestertown, Mary... (United States of America)

35.99 ft.

1972

Used

1972 Islander cruising sailboat with wind generator and solar panels. This is not just any 1972 Islander 36, this beauty has been lightly used and she has been heav...

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$19,900

Westsail 42

Baltimore, Maryland (United States of America)

41.99 ft.

1978

Used

Nice Westsail Cruiser! These boats have sailed all over the world. New Captain wanted! A True Bluewater boat!! Thinking of sailing across the Atlantic or sailing ...

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$59,000

* Price displayed is based on today's currency conversion rate of the listed sales price.