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Sailboats for Sale in Maryland - Discover the Sailboat of Your Dreams, or sell your current Maryland Sailboat to get ready for a new adventure today.
Your search returned 718 matches of 109924 sailboats posted to date

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Morgan 45-4 Merik/Nelson
1983 Tracys Landing MD Maryland 45 Morgan 45-4 Merik/Nelson
Length: 45'     Beam:  13'     Draft:  5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing MD, Maryland
Asking: $35,000
Sailboat Added 23-Jan-2023  More Details

Hallberg Rassy HR Kutter 94
1984 Cambridge Maryland 30 Hallberg Rassy HR Kutter 94
Length: 30'     Beam:  10'     Draft:  4'
Year: 1984
Type: motorsailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Cambridge, Maryland
Asking: $65,000
Sailboat Added 17-Jan-2023  More Details

MacGregor 26X
1998 Earleville MD Cecil County Maryland 26 MacGregor 26X
Length: 26'     Beam:  8'     Draft:  2'
Year: 1998
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Earleville MD Cecil County, Maryland
Asking: $14,995
Sailboat Added 14-Jan-2023  More Details



Tartan 27
1976 Mayo Maryland 27 Tartan 27
Length: 27'     Beam:  8.5'     Draft:  3'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mayo, Maryland
Asking: $1,500
Sailboat Added 06-Jan-2023  More Details

Seidelmann S299
Seidelmann S299
Length: 29'     Beam:  11'     Draft:  5'6'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: North East, Maryland
Asking: $13,500
Sailboat Added 07-Dec-2022  More Details

Bauretek Bauer 10
Bauretek Bauer 10
Length: 10'     Draft:  1'
Year: 2004
Type: dinghy
Hull: fiberglass  monohull
Location: Annapolis, Maryland
Asking: $2,750
Sailboat Added 03-Dec-2022  More Details

O'Day Daysailer
1980 Arnold Maryland 17 O'Day Daysailer
Length: 17'     Beam:  6.25'     Draft:  0.68'
Year: 1980
Type: daysailer
Hull: fiberglass  monohull
Engine: gas outboard
Location: Arnold, Maryland
Asking: $1,500
Sailboat Added 26-Nov-2022  More Details

C&C C&C 29-2
1983 Tracys Landing Maryland 29 C&C C&C 29-2
Length: 29'     Beam:  10'     Draft:  5'3'
Year: 1983
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $15,000
Sailboat Added 23-Nov-2022  More Details

Helleman trimaran
1993 eastern Caribbean Maryland 55 Helleman trimaran
Length: 55'     Beam:  22'     Draft:  5'
Year: 1993
Type: cruiser
Hull: steel  monohull
Engine: 1 diesel inboard
Location: eastern Caribbean, Maryland
Asking: $70,000
Sailboat Added 18-Nov-2022  More Details



Sumner Sailing Dinghy
1972 Easton Maryland 9 Sumner Sailing Dinghy
Length: 9'     Beam:  4'6'
Year: 1972
Type: other
Hull: fiberglass  monohull
Location: Easton, Maryland
Asking: $2,500
Sailboat Added 03-Nov-2022  More Details

Laser
1987 Columbia Maryland 14  Laser
Length: 14'
Year: 1987
Type: dinghy
Hull: fiberglass  monohull
Engine: other inboard
Location: Columbia, Maryland
Asking: $2,500
Sailboat Added 12-Oct-2022  More Details

S2
1985 West Basin Marina Patuxent River Maryland 27 S2
Length: 27'     Beam:  9.2'     Draft:  4.75'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: West Basin Marina Patuxent River, Maryland
Asking: $7,000
Sailboat Added 10-Oct-2022  More Details

AMG Sunfish
 Ocean City Maryland 14 AMG Sunfish
Length: 14'
Type: daysailer
Hull: fiberglass  monohull
Engine: other inboard
Location: Ocean City, Maryland
Asking: $850
Sailboat Added 09-Oct-2022  More Details

Catalina 27
Catalina 27
Length: 27'     Beam:  8'     Draft:  4'
Year: 1987
Type: cruiser
Hull: fiberglass  monohull
Engine: 0 gas outboard
Location: Back Creek Annapolis, Maryland
Asking: $2,500
Sailboat Added 05-Oct-2022  More Details

Southcoast 23
Southcoast 23
Length: 23'     Beam:  7'5'     Draft:  2'10'
Year: 1966
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Rock Hall, Maryland
Asking: $1,500
Sailboat Added 05-Oct-2022  More Details

Allied 39 Sold
1970 Annapolis Maryland 39.10 Allied 39 Sold
Length: 39.10'     Beam:  10.5'     Draft:  6'
Year: 1970
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $25,000
Sailboat Added 23-Sep-2022  More Details

Beneteau Oceanis 51.1
Beneteau Oceanis 51.1
Length: 51'     Beam:  15.75'     Draft:  6.3'
Year: 2020
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chesapeake Bay, Maryland
Asking: $650,000
Sailboat Added 21-Sep-2022  More Details

Pearson Yachts Pearson 40
Pearson Yachts Pearson 40
Length: 39.92'     Beam:  12.5'     Draft:  4.25'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $30,000
Sailboat Added 20-Sep-2022  More Details

Helms
1982 Deale Maryland 27 Helms
Length: 27'     Beam:  9.67'     Draft:  4.3'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Deale, Maryland
Asking: $10,000
Sailboat Added 18-Sep-2022  More Details



Hunter Cherubini 30 Sloop
1981 Worton Creek Maryland Maryland 30 Hunter Cherubini 30 Sloop
Length: 30'     Beam:  12'     Draft:  4'
Year: 1981
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Worton Creek Maryland, Maryland
Asking: $11,000
Sailboat Added 12-Sep-2022  More Details

Laser II
 Arnold Maryland 14 Laser II
Length: 14'     Beam:  5'     Draft:  .5'
Type: dinghy
Hull: fiberglass  monohull
Location: Arnold, Maryland
Asking: $5,000
Sailboat Added 10-Sep-2022  More Details

Catalina 445
2011 Tracys Landing Maryland 44.5 Catalina 445
Length: 44.5'     Beam:  15'     Draft:  5.9'
Year: 2011
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Tracys Landing, Maryland
Asking: $325,000
Sailboat Added 09-Sep-2022  More Details

Tartan 28
1984 Tall Timbers Maryland 28 Tartan 28
Length: 28'     Beam:  10'     Draft:  4-11'
Year: 1984
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tall Timbers, Maryland
Asking: $18,600
Sailboat Added 08-Sep-2022  More Details

Irwin 38 Center Cockpit
Irwin 38 Center Cockpit
Length: 39'10'     Beam:  12'6'     Draft:  4'6'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Edgewater, Maryland
Asking: $49,900
Sailboat Added 06-Sep-2022  More Details

Performance Cruising Gemini 30
Performance Cruising Gemini 30
Length: 30'     Beam:  13'     Draft:  1'3'
Year: 1988
Type: cruiser
Hull: fiberglass  catamaran
Engine: 1 gas outboard
Location: Shady Side, Maryland
Asking: $35,700
Sailboat Added 06-Sep-2022  More Details

Hake Seaward 25
1998 Bohemia Bay Maryland 25 Hake Seaward 25
Length: 25'     Beam:  83'     Draft:  21'
Year: 1998
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Bohemia Bay, Maryland
Asking: $24,995
Sailboat Added 29-Aug-2022  More Details

Hunter 25.5
1985 Galesville Maryland 25.5 Hunter 25.5
Length: 25.5'     Beam:  9'     Draft:  4.5'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Galesville, Maryland
Asking: $6,500
Sailboat Added 26-Aug-2022  More Details

O'Day 28 CB
1984 Tall Timbers Maryland 28.25 O'Day 28 CB
Length: 28.25'     Beam:  10.25'     Draft:  3.25'
Year: 1984
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 other inboard
Location: Tall Timbers, Maryland
Asking: $6,000
Sailboat Added 18-Aug-2022  More Details

Grabner GmbH Happy Cat Neo
2022 Rosedale MD Maryland 13.78 Grabner GmbH Happy Cat Neo
Length: 13.78'     Beam:  6.73'     Draft:  1.6'
Year: 2022
Type: dinghy
Hull: other  catamaran
Location: Rosedale MD, Maryland
Asking: $9,500
Sailboat Added 20-Aug-2022  More Details

SOLD Island Packet 380 380
1999 Rock Hall Maryland 39 SOLD Island Packet 380 380
Length: 39'     Beam:  13'     Draft:  5.5'
Year: 1999
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Rock Hall, Maryland
Asking: $199,000
Sailboat Added 11-Aug-2022  More Details

Hout Bay 40 Steel Schooner
1988 Galesville Maryland 50 Hout Bay 40 Steel Schooner
Length: 50'     Beam:  13'8'     Draft:  6'
Year: 1988
Hull: steel  monohull
Engine: 1 diesel inboard
Location: Galesville, Maryland
Asking: $95,000
Sailboat Added 08-Mar-2024  More Details



Allied 42 XL-2
1976 Annapolis Maryland 42 Allied 42 XL-2
Length: 42'     Beam:  11.5'     Draft:  4.2'
Year: 1976
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $35,000
Sailboat Added 05-Aug-2022  More Details

Downeast Cutter
1977 Annapolis Mill Creek Maryland 38 Downeast Cutter
Length: 38'     Beam:  12'     Draft:  5'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis Mill Creek, Maryland
Asking: $42,500
Sailboat Added 15-Sep-2024  More Details

CE Ryder Southern Cross 31
CE Ryder Southern Cross 31
Length: 31'     Beam:  9.6'     Draft:  4.5'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tyaskin, Maryland
Asking: $26,500
Sailboat Added 29-Jul-2022  More Details

Hunter 216
2006 Grays Creek on the Magothy Maryland 21.5 Hunter 216
Length: 21.5'     Beam:  8'     Draft:  1'
Year: 2006
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 other outboard
Location: Grays Creek on the Magothy, Maryland
Asking: $4,900
Sailboat Added 25-Sep-2022  More Details

Farrier TrailerTri 720
1980 Kingsville Maryland 23 Farrier TrailerTri 720
Length: 23'     Beam:  16.5'     Draft:  1.5'
Year: 1980
Type: cruiser
Hull: wood  trimaran
Location: Kingsville, Maryland
Asking: $12,500
Sailboat Added 03-Jul-2022  More Details

c&c 30 MK1
1975 edgewater maryland Maryland 30 c&c 30 MK1
Length: 30'     Beam:  10'     Draft:  5'
Year: 1975
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: edgewater maryland, Maryland
Asking: $10,000
Sailboat Added 01-Jul-2022  More Details

Tillotson Pearson Inc Freedom 21
1983 Solomons MD Maryland 21'8 Tillotson Pearson Inc Freedom 21
Length: 21'8'     Beam:  8''     Draft:  3'9'
Year: 1983
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Solomons MD, Maryland
Asking: $4,500
Sailboat Added 27-Jun-2022  More Details

Aloha Yachts Sailboat
Aloha Yachts Sailboat
Length: 27'     Beam:  9' 6'     Draft:  4' 4'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chesapeake Bay South of Annapolis, Maryland
Asking: $13,500
Sailboat Added 23-Jun-2022  More Details

Com-Pac 16
Com-Pac 16
Length: 16'     Beam:  6'     Draft:  18'
Year: 1979
Type: daysailer
Hull: fiberglass  monohull
Location: Shady Side, Maryland
Asking: $1,200
Sailboat Added 21-Jun-2022  More Details

Com-Pac 27/2
1989 Annapolis Maryland 27 Com-Pac 27/2
Length: 27'     Beam:  9.5'     Draft:  3.5'
Year: 1989
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $19,500
Sailboat Added 02-Jun-2022  More Details

Endeavour Yachts Sloop
1977 Tracys Landing Maryland 32 Endeavour Yachts Sloop
Length: 32'     Beam:  10'     Draft:  4'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $8,500
Sailboat Added 01-Jun-2022  More Details

Tayana Custom 52
1988 Tolchester Maryland 52 Tayana Custom 52
Length: 52'     Beam:  15'     Draft:  6.5'
Year: 1988
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tolchester, Maryland
Asking: $385,000
Sailboat Added 25-May-2022  More Details

Hunter 41 DS
Hunter 41 DS
Length: 41'     Beam:  13.25'     Draft:  5'
Year: 2008
Type: motorsailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $137,500
Sailboat Added 25-May-2022  More Details

Tartan T-10
1978 Annapolis Maryland 33 Tartan T-10
Length: 33'     Beam:  9'     Draft:  5.9'
Year: 1978
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $7,900
Sailboat Added 11-May-2022  More Details

J Boats J29 MHOB
1985 Cambridge Maryland 29 J Boats J29 MHOB
Length: 29'     Beam:  11'     Draft:  5.6'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Cambridge, Maryland
Asking: $13,500
Sailboat Added 08-May-2022  More Details

Hunter 36
2005 Deale MD Maryland 36 Hunter 36
Length: 36'     Beam:  12'     Draft:  5'
Year: 2005
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Deale MD, Maryland
Asking: $75,000
Sailboat Added 06-May-2022  More Details

newport Mark III
1985 Worton Creek Maryland 30 newport Mark III
Length: 30'     Beam:  10.6'     Draft:  5.1'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Worton Creek, Maryland
Asking: $16,500
Sailboat Added 04-May-2022  More Details

Morgan 382
Morgan 382
Length: 38'4'     Beam:  12'     Draft:  5'6'
Year: 1981
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $32,000
Sailboat Added 29-Apr-2022  More Details

Laser Preformance Laser
Length: 13'9"'     Beam:  4'7"'
Year: 1983
Type: dinghy
Hull: fiberglass  monohull
Location: Ellicott City, Maryland
Asking: $500
Sailboat Added 19-Apr-2022  More Details

Ranger 30
1978 Annapolis Maryland 30 Ranger 30
Length: 30'     Beam:  10.75'     Draft:  5.5'
Year: 1978
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Sailboat Added 09-Apr-2022  More Details

Catalina 30
Catalina 30
Length: 30'     Beam:  11'     Draft:  4'4'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Whitehall Yacht Yard Annapolis, Maryland
Asking: $15,000
Sailboat Added 08-Apr-2022  More Details

O'Day
1986 Tolchester Marina Tolchester Beach Chestertown Maryland 28'3
Length: 28'3"'     Beam:  10'3'     Draft:  4'8'
Year: 1986
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tolchester Marina Tolchester Beach Chestertown, Maryland
Asking: $12,500
Sailboat Added 28-Mar-2022  More Details

Cal 35 MKII
1983 Flag Harbor in Saint Leonard Maryland 35 Cal 35 MKII
Length: 35'     Beam:  11'     Draft:  5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Flag Harbor in Saint Leonard, Maryland
Asking: $21,000
Sailboat Added 28-Apr-2025  More Details

Hunter 1978 Sloop
Hunter 1978 Sloop
Length: 27'     Beam:  9'     Draft:  4'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Shadyside, Maryland
Asking: $5,800
Sailboat Added 26-Mar-2022  More Details

Beneteau 281
1997 Annapolis Maryland 28 Beneteau 281
Length: 28'     Beam:  9.5'     Draft:  4'
Year: 1997
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $30,000
Sailboat Added 20-Mar-2022  More Details

Laser Laser
1982 Saint Leonard Maryland 14 Laser Laser
Length: 14'
Year: 1982
Type: dinghy
Hull: fiberglass  monohull
Location: Saint Leonard, Maryland
Asking: $1,200
Sailboat Added 06-Mar-2022  More Details

Tanzer T22
1986 Delmarva Peninsula Maryland 22.50 Tanzer T22
Length: 22.50'     Beam:  7.83'     Draft:  3.42'
Year: 1986
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Delmarva Peninsula, Maryland
Asking: $5,000
Sailboat Added 02-Mar-2022  More Details

Amsterdam Shipyard G de Vries Lentsch TRIPP 29
Amsterdam Shipyard G de Vries Lentsch TRIPP 29
Length: 28.9'     Beam:  8.96'     Draft:  4.5'
Year: 1964
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: St Michaels, Maryland
Asking: $15,000
Sailboat Added 28-Feb-2022  More Details

Catalina Catalina 30 Tall Rig
Catalina Catalina 30 Tall Rig
Length: 30'     Beam:  10.83'     Draft:  4.5'
Year: 1986
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $10,000
Sailboat Added 27-Feb-2022  More Details

Jeanneau Arcadia
1985 Annapolis Maryland 29.75 Jeanneau Arcadia
Length: 29.75'     Beam:  10.5'     Draft:  4.7'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $7,000
Sailboat Added 25-Feb-2022  More Details

Catalina C320 fractional
Catalina C320 fractional
Length: 32'     Beam:  12'     Draft:  4.5'
Year: 2001
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore, Maryland
Asking: $24,000
Sailboat Added 12-Feb-2022  More Details

Hunter 39 Wing Keel
Hunter 39 Wing Keel
Length: 39'     Beam:  12'11'     Draft:  5'
Year: 2011
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Middle River, Maryland
Asking: $133,000
Sailboat Added 28-Jan-2022  More Details

Catalina 30
Catalina 30
Length: 30'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Annapolis, Maryland
Asking: $13,500
Sailboat Added 31-Dec-2021  More Details

Cornish Crabber Crabber
Cornish Crabber Crabber
Length: 17'     Beam:  6' 9'     Draft:  1'4'
Year: 2001
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: St Michaels, Maryland
Asking: $8,200
Sailboat Added 24-Jun-2022  More Details

Pearson Pearson 26
Length: 26'     Beam:  8'     Draft:  4'
Year: 1975
Type: cruiser
Hull: fiberglass  monohull
Engine: gas outboard
Location: ANNAPOLIS, Maryland
Asking: $3,000
Sailboat Added 23-Nov-2021  More Details



Catalina 30
1985 Tracys Landing Maryland 30 Catalina 30
Length: 30'     Beam:  11'     Draft:  5.5'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $13,500
Sailboat Added 16-Nov-2021  More Details

CAL CAL 28
1986 Severna Park Maryland 28'3 CAL CAL 28
Length: 28'3'     Beam:  10'8'     Draft:  5' 3'
Year: 1986
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Severna Park, Maryland
Asking: $28,000
Sailboat Added 26-Oct-2021  More Details

Beneteau First 44.7
Beneteau First 44.7
Length: 44'     Beam:  13'     Draft:  6'8'
Year: 2005
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $215,000
Sailboat Added 30-Sep-2022  More Details


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