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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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Hunter
1983 Deale MD Maryland 34 Hunter
Length: 34'     Beam:  11'     Draft:  5.5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Deale MD, Maryland
Asking: $7,000
Sailboat Added 28-Aug-2025  More Details

Com-Pac 27-2
1994 Mayo Maryland 27 Com-Pac 27-2
Length: 27'     Beam:  9.5'     Draft:  3.5'
Year: 1994
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mayo, Maryland
Asking: $15,900
Sailboat Added 26-Aug-2025  More Details

J Boats J22
1984 Annapolis Maryland 22 J Boats J22
Length: 22'     Beam:  8'     Draft:  3.5'
Year: 1984
Type: racer
Hull: fiberglass  monohull
Location: Annapolis, Maryland
Asking: $7,000
Sailboat Added 22-Aug-2025  More Details



Moody 425
Moody 425
Length: 42'     Beam:  13'     Draft:  6'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Sailing Assoc on Sassafrass River, Maryland
Asking: $78,000
Sailboat Added 20-Aug-2025  More Details

Featured Sailboat:  Caliber 40
1994 Oxford Maryland 40 Caliber 40
Length: 40'     Beam:  12.6'     Draft:  5.2'
Year: 1994
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Oxford, Maryland
Asking: $70,000
Featured Sailboat Added 20-Aug-2025  More Details

J Boats J27
1985 North Beach Maryland 27 J Boats J27
Length: 27'     Beam:  8.5'     Draft:  5'
Year: 1985
Type: racer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: North Beach, Maryland
Asking: $12,000
Sailboat Added 19-Aug-2025  More Details

Columbia Yacht Columbia 9.6
1978 Pasadena Maryland 32 Columbia Yacht Columbia 9.6
Length: 32'     Beam:  10'     Draft:  5'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Pasadena, Maryland
Asking: $16,500
Sailboat Added 17-Aug-2025  More Details

Beneteau Oceanis 40
2011 Pasadena Maryland 40 Beneteau Oceanis 40
Length: 40'     Beam:  13'     Draft:  6.5'
Year: 2011
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Pasadena, Maryland
Asking: $159,000
Sailboat Added 17-Aug-2025  More Details

Beneteau Oceanis 40
2010 Baltimore Maryland 40 Beneteau Oceanis 40
Length: 40'     Beam:  12.8'     Draft:  5.5'
Year: 2010
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore, Maryland
Asking: $120,000
Sailboat Added 16-Aug-2025  More Details



Voyage 440
2007 Annapolis Maryland 44 Voyage 440
Length: 44'     Beam:  25.52'     Draft:  4.1'
Year: 2007
Type: cruiser
Hull: fiberglass  catamaran
Engine: 2 diesel inboard
Location: Annapolis, Maryland
Asking: $330,000
Sailboat Added 15-Aug-2025  More Details

Morgan 384
1983 Chestertown Maryland 38 Morgan 384
Length: 38'     Beam:  12'     Draft:  5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Chestertown, Maryland
Asking: $25,000
Sailboat Added 08-Aug-2025  More Details

Cape Dory CD 30
1982 Centreville Maryland 30 Cape Dory CD 30
Length: 30'     Beam:  9'     Draft:  4'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Centreville, Maryland
Asking: $15,000
Sailboat Added 08-Aug-2025  More Details

Featured Sailboat:  Tayana Tayana 37
1979 Centreville Maryland 41 Tayana Tayana 37
Length: 41'     Beam:  11.5'     Draft:  5.7'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Centreville, Maryland
Asking: $45,000
Featured Sailboat Added 09-Aug-2025  More Details

Tartan Yachts t37 Tartan Marine Sparkman & Stephens Bluewater Sloop
1980 Annapolis Maryland 37 Tartan Yachts t37 Tartan Marine Sparkman & Stephens Bluewater Sloop
Length: 37'     Beam:  12'     Draft:  4'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $28,750
Sailboat Added 04-Aug-2025  More Details

Westsail 42
1974 Baltimore Maryland 42 Westsail 42
Length: 42'     Beam:  13'     Draft:  5'8'
Year: 1974
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore, Maryland
Asking: $35,000
Sailboat Added 02-Aug-2025  More Details

Sabre 36 Racer/cruiser
1985 Essex Maryland 36 Sabre 36 Racer/cruiser
Length: 36'     Beam:  12'     Draft:  6'4'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Essex, Maryland
Asking: $55,000
Sailboat Added 01-Aug-2025  More Details

Hunter 30t
1988 Galena Maryland 30.6 Hunter 30t
Length: 30.6'     Beam:  11.5'     Draft:  4'
Year: 1988
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Galena, Maryland
Asking: $24,950
Sailboat Added 31-Jul-2025  More Details

Featured Sailboat:  Hunter 41 DS
2012 Solomons Maryland 41 Hunter 41 DS
Length: 41'     Beam:  13'3'     Draft:  5'
Year: 2012
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Solomons, Maryland
Asking: $165,000
Featured Sailboat Added 30-Jul-2025  More Details

Cape Dory
1976 213 N Talbot Street Saint Michaels Maryland 25 Cape Dory
Length: 25'
Year: 1976
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: 213 N Talbot Street Saint Michaels, Maryland
Asking: $6,500
Sailboat Added 29-Jul-2025  More Details



J Boats J/24
J Boats J/24
Length: 24'     Beam:  8.9'     Draft:  4'
Year: 1984
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 other outboard
Location: Edgewater-Annapolis, Maryland
Asking: $5,490
Sailboat Added 26-Jul-2025  More Details

Catalina Yachts Catalina 30MKIII
Catalina Yachts Catalina 30MKIII
Length: 30'     Beam:  11'     Draft:  4'
Year: 1994
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Middle River MD, Maryland
Asking: $32,000
Sailboat Added 25-Jul-2025  More Details

Featured Sailboat:  Irwin Citation 31
1985 Tracys Landing Maryland 31.00 Irwin Citation 31
Length: 31.00'     Beam:  11'     Draft:  5'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $15,000
Featured Sailboat Added 25-Jul-2025  More Details

Featured Sailboat:  Bristol 29.9
1981 Chesapeake western shore Maryland 29.9 Bristol 29.9
Length: 29.9'     Beam:  10.17'     Draft:  4.33'
Year: 1981
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chesapeake western shore, Maryland
Asking: $10,900
Featured Sailboat Added 05-Aug-2025  More Details

Featured Sailboat:  Camper & Nicholson 35
1976 Annapolis Maryland 35 Camper & Nicholson 35
Length: 35'     Beam:  11'     Draft:  5.5'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Annapolis, Maryland
Asking: $25,000
Featured Sailboat Added 21-Jul-2025  More Details

Pearson Vanguard
Pearson Vanguard
Length: 33'     Beam:  9'6'
Year: 1967
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Edgewater, Maryland
Asking: $6,400
Sailboat Added 19-Jul-2025  More Details

Featured Sailboat:  Catalina CM440
Catalina CM440
Length: 46''     Beam:  14'     Draft:  511'
Year: 2005
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chesapeake Bay, Maryland
Asking: $215,000
Featured Sailboat Added 19-Jul-2025  More Details

Featured Sailboat:  Pearson 386
1984 Mayo Maryland 38.3 Pearson 386
Length: 38.3'     Beam:  11.5'     Draft:  5.5'
Year: 1984
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mayo, Maryland
Asking: $42,500
Featured Sailboat Added 19-Jul-2025  More Details

Heritage Marine Nor'Sea 27
1980 Chesapeake Bay Maryland 27 Heritage Marine Nor'Sea 27
Length: 27'     Beam:  8'     Draft:  4'
Year: 1980
Type: motorsailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chesapeake Bay, Maryland
Asking: $20,000
Sailboat Added 14-Jul-2025  More Details

CW Hood Design Scheel keel
CW Hood Design Scheel keel
Length: 32'
Year: 2015
Type: cruiser
Hull: fiberglass  monohull
Engine: other inboard
Location: Annapolis, Maryland
Asking: $125,000
Sailboat Added 11-Jul-2025  More Details

Capri
1995 Saint Michaels Maryland 16.5 Capri
Length: 16.5'
Year: 1995
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Saint Michaels, Maryland
Asking: $4,000
Sailboat Added 08-Jul-2025  More Details

Hobie Tandem Mirage Sailing Kayak
2017 Delmar Maryland 17 Hobie Tandem Mirage Sailing Kayak
Length: 17'     Beam:  2.5'     Draft:  1'
Year: 2017
Type: daysailer
Hull: fiberglass  monohull
Engine: other outboard
Location: Delmar, Maryland
Asking: $5,500
Sailboat Added 08-Jul-2025  More Details



Seaward Fox
1993 Frederick Maryland 19'9' Seaward Fox
Length: 19'9''     Beam:  8'     Draft:  3'
Year: 1993
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Frederick, Maryland
Asking: $4,000
Sailboat Added 08-Jul-2025  More Details

Bristol 40/40
1980 Stevensville Maryland 40 Bristol 40/40
Length: 40'     Beam:  10'     Draft:  7'
Year: 1980
Type: other
Hull: fiberglass  
Engine: 1 diesel inboard
Location: Stevensville, Maryland
Asking: $37,500
Sailboat Added 03-Jul-2025  More Details

Morgan 323
1983 Middle River Maryland 32 Morgan 323
Length: 32'     Beam:  11.5'     Draft:  5.3'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Middle River, Maryland
Asking: $12,900
Sailboat Added 01-Jul-2025  More Details

Featured Sailboat:  Hunter 356
Hunter 356
Length: 35.6'     Beam:  12'     Draft:  5'
Year: 2003
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $54,500
Featured Sailboat Added 01-Jul-2025  More Details

Oday
Oday
Length: 22'
Year: 1980
Type: daysailer
Hull: fiberglass  monohull
Engine: gas outboard
Location: 213 N Talbot Street, Maryland
Asking: $3,500
Sailboat Added 26-Jun-2025  More Details

Precision Colgate 26
Precision Colgate 26
Length: 25.7'     Beam:  8.5'     Draft:  3.5'
Year: 1998
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Annapolis, Maryland
Asking: $14,800
Sailboat Added 25-Jun-2025  More Details

Nautor Swan Swan 40
1971 AnnapolisBaltimore Maryland 40 Nautor Swan Swan 40
Length: 40'     Beam:  11'     Draft:  6.8'
Year: 1971
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: AnnapolisBaltimore, Maryland
Asking: $39,000
Sailboat Added 23-Jun-2025  More Details

Beneteau 40.7
1999 Muskegon Maryland 40 Beneteau 40.7
Length: 40'     Beam:  12'     Draft:  8'
Year: 1999
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Muskegon, Maryland
Asking: $89,000
Sailboat Added 22-Jun-2025  More Details

COM-PAC 27/2
1993 near Annapolis Maryland 29'-1 COM-PAC 27/2
Length: 29'-1'     Beam:  9'-6'     Draft:  3'-6'
Year: 1993
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: near Annapolis, Maryland
Asking: $13,000
Sailboat Added 19-Jun-2025  More Details

Hughes Northstar 1500
Hughes Northstar 1500
Length: 35.6'     Beam:  10.4'     Draft:  5.8'
Year: 1980
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore, Maryland
Asking: $6,000
Sailboat Added 12-Jun-2025  More Details

Hunter 14
2019 Saint Michaels Maryland 14 Hunter 14
Length: 14'     Beam:  5'     Draft:  3'
Year: 2019
Type: daysailer
Hull: fiberglass  monohull
Engine: gas inboard
Location: Saint Michaels, Maryland
Asking: $5,500
Sailboat Added 11-Jun-2025  More Details

Catspaw
1998 Saint Michaels Maryland 13 Catspaw
Length: 13'     Beam:  4.5'     Draft:  .5'
Year: 1998
Type: dinghy
Hull: wood  monohull
Location: Saint Michaels, Maryland
Asking: $6,000
Sailboat Added 11-Jun-2025  More Details

C E Ryder Southern Cross 39
C E Ryder Southern Cross 39
Length: 39'     Beam:  12'     Draft:  5.3'
Year: 1981
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $50,000
Sailboat Added 11-Jun-2025  More Details

Contest 46 / 48
1995 Annapolis Maryland 48 Contest 46 / 48
Length: 48'     Beam:  14'     Draft:  6'
Year: 1995
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Annapolis, Maryland
Asking: $165,000
Sailboat Added 10-Jun-2025  More Details

Passport 51CC
Passport 51CC
Length: 51.1'     Beam:  14.5'     Draft:  7.1'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Solomons, Maryland
Asking: $189,000
Sailboat Added 09-Jun-2025  More Details

Irwin Citation 34
1985 Mayo Maryland 34 Irwin Citation 34
Length: 34'     Beam:  11.25'     Draft:  4'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mayo, Maryland
Asking: $9,990
Sailboat Added 03-Jun-2025  More Details

Hunter 31
1984 Mayo Maryland 31 Hunter 31
Length: 31'     Beam:  11'     Draft:  4'
Year: 1984
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mayo, Maryland
Asking: $11,750
Sailboat Added 03-Jun-2025  More Details

Catalina 36
1990 North East MD Maryland 36 Catalina 36
Length: 36'     Beam:  11'11'     Draft:  4'5'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: gas inboard
Location: North East MD, Maryland
Asking: $65,000
Sailboat Added 03-Jun-2025  More Details

Cal Cal 33-2
Cal Cal 33-2
Length: 33'     Beam:  11.3'     Draft:  4.6'
Year: 1988
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Worton, Maryland
Asking: $21,000
Sailboat Added 31-May-2025  More Details

Hunter 33
Hunter 33
Length: 33.6'     Beam:  12'     Draft:  4.6'
Year: 2004
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $59,950
Sailboat Added 30-May-2025  More Details

Cal 39
1979 Edgewater Maryland 39 Cal 39
Length: 39'     Beam:  12'     Draft:  5.6'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Edgewater, Maryland
Asking: $20,000
Sailboat Added 26-May-2025  More Details

Beneteau 411
1998 Havre de Grace Maryland 41 Beneteau 411
Length: 41'     Beam:  13'     Draft:  4.75'
Year: 1998
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Havre de Grace, Maryland
Asking: $99,000
Sailboat Added 23-May-2025  More Details

Catalina 22
1974 Annapolis Maryland 22 Catalina 22
Length: 22'     Beam:  7'     Draft:  4'
Year: 1974
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Annapolis, Maryland
Asking: $1,000
Sailboat Added 21-May-2025  More Details

Flying Scot Flying Scot
1998 Annapolis Maryland 19 Flying Scot Flying Scot
Length: 19'     Beam:  6.75'     Draft:  2-3.5'
Year: 1998
Type: daysailer
Hull: fiberglass  monohull
Location: Annapolis, Maryland
Asking: $11,000
Sailboat Added 20-May-2025  More Details

Pearson Flyer
1981 Saint Michaels Maryland 29.92 Pearson Flyer
Length: 29.92'     Beam:  11.08'     Draft:  5.75'
Year: 1981
Type: racer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Saint Michaels, Maryland
Asking: $5,000
Sailboat Added 14-May-2025  More Details

C&C 29
1985 Saint Michaels Maryland 29.58 C&C 29
Length: 29.58'     Beam:  10.'     Draft:  5.25'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Saint Michaels, Maryland
Asking: $5,000
Sailboat Added 14-May-2025  More Details

Nonsuch
1984 Saint Micheals Maryland 30 Nonsuch
Length: 30'
Year: 1984
Type: daysailer
Hull: wood  monohull
Engine: diesel inboard
Location: Saint Micheals, Maryland
Asking: $24,000
Sailboat Added 08-May-2025  More Details

Stuart Rhodes 19
Stuart Rhodes 19
Length: 19'     Beam:  7'     Draft:  1'
Year: 2006
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Mayo, Maryland
Asking: $14,999
Sailboat Added 07-May-2025  More Details

Newport 30 mk3
1987 Pasadena Maryland 30 Newport 30 mk3
Length: 30'     Beam:  10.7'     Draft:  5.2'
Year: 1987
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Pasadena, Maryland
Asking: $22,000
Sailboat Added 06-May-2025  More Details

Endeavour 43 Ketch
1981 Annapolis Maryland 43 Endeavour 43 Ketch
Length: 43'     Beam:  14'     Draft:  6.5'
Year: 1981
Type: motorsailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $32,000
Sailboat Added 02-May-2025  More Details

Eastport Pram
2024 Saint Michaels Maryland 8 Eastport Pram
Length: 8'     Beam:  4'     Draft:  2'
Year: 2024
Type: dinghy
Hull: wood  monohull
Location: Saint Michaels, Maryland
Asking: $2,100
Sailboat Added 01-May-2025  More Details

Eastport Pram
2020 Saint Michaels Maryland 8 Eastport Pram
Length: 8'     Beam:  4'     Draft:  2'
Year: 2020
Type: dinghy
Hull: wood  monohull
Location: Saint Michaels, Maryland
Asking: $2,900
Sailboat Added 01-May-2025  More Details

Beetle Cat Catboat
 Saint Michaels Maryland 12 Beetle Cat Catboat
Length: 12'     Beam:  6'     Draft:  2'
Type: daysailer
Hull: wood  monohull
Location: Saint Michaels, Maryland
Asking: $2,500
Sailboat Added 01-May-2025  More Details

Celebrity
1980 Saint Michaels Maryland 19 Celebrity
Length: 19'
Year: 1980
Type: daysailer
Hull: fiberglass  monohull
Engine: gas inboard
Location: Saint Michaels, Maryland
Asking: $4,700
Sailboat Added 01-May-2025  More Details

Irwin Sloop
1976 PARISH CREEK LANDING Maryland 40 Irwin Sloop
Length: 40'     Beam:  11'     Draft:  6' 5'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: PARISH CREEK LANDING, Maryland
Asking: $16,000
Sailboat Added 29-Apr-2025  More Details



Pacific Seacraft Flicka
1979 Deale Maryland 24 Pacific Seacraft Flicka
Length: 24'     Beam:  8'     Draft:  3.25'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Deale, Maryland
Asking: $17,250
Sailboat Added 27-Apr-2025  More Details

Beneteau First 310
1992 Havre De Grace Maryland 31 Beneteau First 310
Length: 31'     Beam:  10.6'     Draft:  4.5'
Year: 1992
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Havre De Grace, Maryland
Asking: $34,900
Sailboat Added 27-Apr-2025  More Details

ComPac 19/2
Length: 19'     Beam:  8'     Draft:  2'
Year: 1986
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 other outboard
Location: Chestertown, Maryland
Asking: $2,000
Sailboat Added 25-Apr-2025  More Details


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