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Your search returned 718 matches of 109924 sailboats posted to date

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Lagoon 420 Owners Version
2009 Annapolis Maryland 42 Lagoon 420 Owners Version
Length: 42'     Beam:  25.5'     Draft:  4.5'
Year: 2009
Type: cruiser
Hull: composite  catamaran
Engine: diesel inboard
Location: Annapolis, Maryland
Asking: $379,000
Sailboat Added 09-Apr-2024  More Details

Pearson 28
1979 Pasadena Md Maryland 28 Pearson 28
Length: 28'     Beam:  9'     Draft:  5'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Pasadena Md, Maryland
Asking: $6,000
Sailboat Added 08-Apr-2024  More Details

Tillotson Pearson Freedom 28 cat ketch
1983 Solomons Maryland 28 Tillotson Pearson Freedom 28 cat ketch
Length: 28'     Beam:  10'     Draft:  4.5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Solomons, Maryland
Asking: $12,500
Sailboat Added 18-May-2025  More Details



Hunter 33
2006 Annapolis Maryland 33 Hunter 33
Length: 33'     Beam:  12'     Draft:  5'
Year: 2006
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $63,000
Sailboat Added 02-Apr-2024  More Details

Ta Chiao Ketch
1980 Georgetown Maryland 54 Ta Chiao Ketch
Length: 54'     Beam:  15'     Draft:  6'9'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Georgetown, Maryland
Asking: $125,000
Sailboat Added 31-Mar-2024  More Details

Allied Boat Company Seawind 30
1965 Northeast Md - On the Hard Maryland 30.5 Allied Boat Company Seawind 30
Length: 30.5'     Beam:  9.25'     Draft:  4.20'
Year: 1965
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Northeast Md - On the Hard, Maryland
Asking: $4,800
Sailboat Added 25-Mar-2024  More Details

Allied Boat Company Seawind 30
1965 Northeast Md - On the Hard Maryland 30.5 Allied Boat Company Seawind 30
Length: 30.5'     Beam:  9.25'     Draft:  4.20'
Year: 1965
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Northeast Md - On the Hard, Maryland
Asking: $4,800
Sailboat Added 25-Mar-2024  More Details

Seaward Fox
1992 Davidsonville  Annapolis Maryland 19 Seaward Fox
Length: 19'     Beam:  8'     Draft:  1.58'
Year: 1992
Type: daysailer
Hull: fiberglass  monohull
Engine: gas inboard
Location: Davidsonville Annapolis, Maryland
Asking: $7,000
Sailboat Added 25-Mar-2024  More Details

Hans Christian MKII
1983 Edgewater Maryland 38 Hans Christian MKII
Length: 38'     Beam:  12.5'     Draft:  6'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Edgewater, Maryland
Asking: $45,000
Sailboat Added 22-Mar-2024  More Details



Endeavour 40 Center Cockpit
1 Essex Maryland 40 Endeavour 40 Center Cockpit
Length: 40'     Beam:  13'     Draft:  5'
Year: 1
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Essex, Maryland
Asking: $78,850
Sailboat Added 18-Mar-2024  More Details

bristol
67 Edgewater Maryland 27 bristol
Length: 27'     Beam:  8'     Draft:  4'
Year: 67
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Edgewater, Maryland
Asking: $3,400
Sailboat Added 11-Mar-2024  More Details

Salona 38
2013  Maryland 37'9 Salona 38
Length: 37'9'     Beam:  12'     Draft:  7'
Year: 2013
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Asking: $138,000
Sailboat Added 02-Mar-2024  More Details

McCurdy and Rhodes designed Tillotson Pearson Yachts Navy 44
McCurdy and Rhodes designed Tillotson Pearson Yachts Navy 44
Length: 44'     Beam:  12.5'     Draft:  7'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis Maryland, Maryland
Asking: $39,500
Sailboat Added 23-Feb-2024  More Details

C&C 35-3
1986 Rock Hall Maryland 34-6 C&C 35-3
Length: 34-6'     Beam:  11-3'     Draft:  4-2'
Year: 1986
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Rock Hall, Maryland
Asking: $29,900
Sailboat Added 11-Feb-2024  More Details

Freedom Yachts Freedom 21
1984 Magothy Marina Maryland 21 Freedom Yachts Freedom 21
Length: 21'     Beam:  8'     Draft:  4'
Year: 1984
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 other outboard
Location: Magothy Marina, Maryland
Asking: $5,500
Sailboat Added 07-Feb-2024  More Details

C&C
1979 Annapolis Maryland 29.6 C&C
Length: 29.6'     Beam:  13'     Draft:  5.3'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Annapolis, Maryland
Asking: $2,250
Sailboat Added 31-Mar-2024  More Details

Bruce Roberts Voyager 495
2001 Georgetown Maryland 50 Bruce Roberts Voyager 495
Length: 50'     Beam:  14' 8'     Draft:  5'10'
Year: 2001
Type: cruiser
Hull: steel  monohull
Engine: 1 diesel inboard
Location: Georgetown, Maryland
Asking: $74,000
Sailboat Added 03-Jan-2025  More Details

William Tripp JrAmerican Boat Building Company 1958 Block Island 40
1958 Severna Park Maryland 33.3 William Tripp JrAmerican Boat Building Company 1958 Block Island 40
Length: 33.3'
Year: 1958
Type: racer/cruiser
Hull: composite  monohull
Engine: 1 gas inboard
Location: Severna Park, Maryland
Asking: $20,000
Sailboat Added 17-Jan-2024  More Details

Custom Dutch Built 60 Custom Center Cockpit
1983 Annapolis Maryland 60 Custom Dutch Built 60 Custom Center Cockpit
Length: 60'     Beam:  18'     Draft:  6.5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $325,000
Sailboat Added 20-Apr-2024  More Details



Corbin 39
1983 Tracys Landing Maryland 41.50 Corbin 39
Length: 41.50'     Beam:  12.08'     Draft:  5.5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $67,500
Sailboat Added 28-May-2024  More Details

Pearson 34
1986 Tracys Landing Maryland 33.92 Pearson 34
Length: 33.92'     Beam:  11.17'     Draft:  5.92'
Year: 1986
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Tracys Landing, Maryland
Asking: $16,500
Sailboat Added 05-Dec-2023  More Details

Passport 47 CC
1985 Annapolis Maryland 47 Passport 47 CC
Length: 47'     Beam:  14'     Draft:  6.5'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $165,000
Sailboat Added 04-Dec-2023  More Details

Cape Dory 28
1977 Cambridge Maryland 28 Cape Dory 28
Length: 28'     Beam:  8'10'     Draft:  4'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Cambridge, Maryland
Asking: $9,000
Sailboat Added 13-Nov-2023  More Details

Tartan 37-2
1980 Herrington Harbor North Marina Maryland 37.3 Tartan 37-2
Length: 37.3'     Beam:  11.75'     Draft:  4.2'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Herrington Harbor North Marina, Maryland
Asking: $45,000
Sailboat Added 17-Mar-2024  More Details

Pearson P-30 Benefits Charity
1973 Baltimore Maryland 30 Pearson P-30   Benefits Charity
Length: 30'     Beam:  9.5'     Draft:  5'
Year: 1973
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore, Maryland
Asking: $7,500
Sailboat Added 01-Nov-2023  More Details

Hake Seaward 26RK
2010 Worton Md Maryland 26 Hake Seaward 26RK
Length: 26'     Beam:  8'     Draft:  1-6'
Year: 2010
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Worton Md, Maryland
Asking: $53,500
Sailboat Added 31-Oct-2023  More Details

C&C Fin Keel
1974 Havre de Grace Maryland 30 C&C Fin Keel
Length: 30'     Beam:  10'     Draft:  5'
Year: 1974
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Havre de Grace, Maryland
Asking: $8,500
Sailboat Added 29-Oct-2023  More Details

L. F. Herreshoff 1976 H-28 GWYLAN
 Oxford Maryland   L. F. Herreshoff 1976 H-28 GWYLAN
Length: '
Type: cruiser
Hull: wood  monohull
Engine: 1 diesel inboard
Location: Oxford, Maryland
Asking: $25,000
Sailboat Added 27-Oct-2023  More Details

Bristol 30
1975 West River MD Maryland 30 Bristol 30
Length: 30'     Beam:  9.5'     Draft:  4.5'
Year: 1975
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: West River MD, Maryland
Asking: $15,400
Sailboat Added 13-Oct-2023  More Details

Gulfstar 41 Ketch
1973 Galesville Maryland 41 Gulfstar 41 Ketch
Length: 41'     Beam:  12'     Draft:  6'
Year: 1973
Type: cruiser
Hull: fiberglass  monohull
Engine: 0 diesel inboard
Location: Galesville, Maryland
Asking: $12,000
Sailboat Added 25-Sep-2023  More Details

Hunter 260
1996 Pasadena Maryland 26 Hunter 260
Length: 26'
Year: 1996
Type: daysailer
Hull: fiberglass  monohull
Engine: gas outboard
Location: Pasadena, Maryland
Asking: $14,500
Sailboat Added 25-Sep-2023  More Details



O'Day 272
1987 Middle River Maryland 27 O'Day 272
Length: 27'     Beam:  9'     Draft:  3'
Year: 1987
Type: cruiser
Hull: fiberglass  monohull
Engine: gas outboard
Location: Middle River, Maryland
Asking: $6,950
Sailboat Added 14-Sep-2023  More Details

Grabner Happy Cat Evolution
2023 Baltimore Maryland 15 Grabner Happy Cat Evolution
Length: 15'     Beam:  7'     Draft:  2'
Year: 2023
Type: daysailer
Hull: other  catamaran
Location: Baltimore, Maryland
Asking: $14,000
Sailboat Added 06-Sep-2023  More Details

MacGregor 26 x sailboat
1998 Earleville MD Hacks Point Maryland 26 MacGregor 26 x sailboat
Length: 26'     Beam:  7'9'     Draft:  1'8'
Year: 1998
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Earleville MD Hacks Point, Maryland
Sailboat Added 27-Aug-2023  More Details

Pearson Pearson 35
1976 Solomons Maryland 35 Pearson Pearson 35
Length: 35'     Beam:  10'     Draft:  3.75'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Solomons, Maryland
Asking: $15,000
Sailboat Added 23-Aug-2023  More Details

O'Day 240
1988 North East MD Maryland 24 O'Day 240
Length: 24'     Beam:  8.25'     Draft:  2.67'
Year: 1988
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: North East MD, Maryland
Asking: $3,500
Sailboat Added 22-Aug-2023  More Details

J Boats J 120
1998 North East Maryland 40 J Boats J 120
Length: 40'     Beam:  12'     Draft:  7'
Year: 1998
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: North East, Maryland
Asking: $150,000
Sailboat Added 08-Aug-2023  More Details

Beneteau First 42
1981 Port Annapolis Marina Annapolis Maryland 42.92 Beneteau First 42
Length: 42.92'     Beam:  13.08'     Draft:  7.25'
Year: 1981
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Port Annapolis Marina Annapolis, Maryland
Asking: $74,900
Sailboat Added 23-Oct-2023  More Details

Featured Sailboat:  Brewer Cutter Ketch
1988 Baltimore Maryland 44 Brewer Cutter Ketch
Length: 44'     Beam:  13.5'     Draft:  5.2-9'
Year: 1988
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore, Maryland
Asking: $85,000
Featured Sailboat Added 03-Aug-2025  More Details

Endeavour 40
Endeavour 40
Length: 40'     Beam:  13'     Draft:  5'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Georgetown, Maryland
Asking: $75,000
Sailboat Added 20-Jul-2023  More Details

Catalina C34 MKI-1/2
1990 Cambridge Maryland 34.6 Catalina C34 MKI-1/2
Length: 34.6'     Beam:  11.75'     Draft:  4.3'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Cambridge, Maryland
Asking: $38,000
Sailboat Added 19-Jul-2023  More Details

Tartan 30c
1975 Cambridge Maryland 30 Tartan 30c
Length: 30'     Beam:  10.00'     Draft:  5'
Year: 1975
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Cambridge, Maryland
Asking: $10,000
Sailboat Added 14-Jul-2023  More Details

Montgomery 23
1979 Rock Hall Maryland 23 Montgomery 23
Length: 23'     Beam:  8'     Draft:  2.5'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Rock Hall, Maryland
Asking: $16,500
Sailboat Added 11-Jul-2023  More Details

Allied 42 Xl-2
1976 Annapolis Maryland 41.5 Allied 42 Xl-2
Length: 41.5'     Beam:  11.5'     Draft:  4.5'
Year: 1976
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $35,000
Sailboat Added 10-Jul-2023  More Details

CATALINA 350
CATALINA 350
Length: 35'     Beam:  13'     Draft:  4.5'
Year: 2004
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Selby Bay Edgewater, Maryland
Asking: $110,000
Sailboat Added 08-Jul-2023  More Details

Dickerson 36 Ketch
1972 Magothy River Chesapeake Bay Maryland 36 Dickerson 36 Ketch
Length: 36'     Beam:  11'     Draft:  4'
Year: 1972
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Magothy River Chesapeake Bay, Maryland
Asking: $10,000
Sailboat Added 03-Jun-2024  More Details

XCat Xcat sail with RowVista
XCat Xcat sail with RowVista
Length: 16.40'     Beam:  7.21'     Draft:  0.5'
Year: 2021
Type: racer/cruiser
Hull: fiberglass  catamaran
Location: Annapolis, Maryland
Asking: $11,000
Sailboat Added 29-Jun-2023  More Details

Flying Scot
2008 St Michaels Maryland 19 Flying Scot
Length: 19'     Beam:  6'     Draft:  4'
Year: 2008
Type: racer
Hull: fiberglass  monohull
Engine: 1 other outboard
Location: St Michaels, Maryland
Asking: $7,500
Sailboat Added 22-Jun-2023  More Details

Laser Performance Laser
Length: 13.9''
Year: 2014
Type: dinghy
Hull: fiberglass  monohull
Engine: inboard
Location: Annapolis, Maryland
Asking: $8,000
Sailboat Added 17-Jun-2023  More Details

Catalina 34
1988 Rock Hall Maryland 34 Catalina 34
Length: 34'     Beam:  12'     Draft:  4'
Year: 1988
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Rock Hall, Maryland
Asking: $39,900
Sailboat Added 19-Jun-2023  More Details

O Day 37 CC
1979 Baltimore Maryland 37 O Day 37 CC
Length: 37'     Beam:  11.6'     Draft:  5.9'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore, Maryland
Asking: $25,000
Sailboat Added 15-Jun-2023  More Details

Columbia 8.7
1976 Edgewater Maryland 29 Columbia 8.7
Length: 29'     Beam:  10'     Draft:  4.5'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Edgewater, Maryland
Asking: $8,500
Sailboat Added 12-Jun-2023  More Details

Tanzer Pilothouse
Tanzer Pilothouse
Length: 35'     Beam:  11.5'     Draft:  5'
Year: 1986
Type: motorsailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mayo md, Maryland
Asking: $25,000
Sailboat Added 01-Jun-2023  More Details

Hunter Cherubini
1980 Havre de Grace Maryland 30 Hunter Cherubini
Length: 30'     Draft:  5'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Havre de Grace, Maryland
Asking: $12,500
Sailboat Added 23-May-2023  More Details

Thistle
 Annapolis Maryland 17  Thistle
Length: 17'     Beam:  6'     Draft:  3'
Type: daysailer
Hull: fiberglass  monohull
Location: Annapolis, Maryland
Asking: $1,800
Sailboat Added 22-May-2023  More Details

Schock Wavelength 24
1984 Annapolis Maryland 24 Schock Wavelength 24
Length: 24'     Beam:  9'     Draft:  4.5'
Year: 1984
Type: racer
Hull: fiberglass  monohull
Engine: gas inboard
Location: Annapolis, Maryland
Asking: $5,000
Sailboat Added 15-May-2023  More Details

O'Day 240
1988 Oxford Maryland 24 O'Day 240
Length: 24'     Beam:  8.25'     Draft:  2.67'
Year: 1988
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Oxford, Maryland
Asking: $7,200
Sailboat Added 08-May-2023  More Details

Zuma
 Rockville Maryland 13  Zuma
Length: 13'
Type: dinghy
Hull: fiberglass  monohull
Engine: gas inboard
Location: Rockville, Maryland
Asking: $2,500
Sailboat Added 05-May-2023  More Details

Astus 14.5
2023 Baltimore Maryland 14.27 Astus 14.5
Length: 14.27'     Beam:  7.9'     Draft:  2'
Year: 2023
Type: dinghy
Hull: fiberglass  trimaran
Location: Baltimore, Maryland
Asking: $10,000
Sailboat Added 13-Apr-2023  More Details

Beneteau 311
2001 Baltimore Inner Harbor Maryland 31 Beneteau 311
Length: 31'     Beam:  10.5'     Draft:  4.7'
Year: 2001
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Baltimore Inner Harbor, Maryland
Asking: $56,500
Sailboat Added 08-Apr-2023  More Details

Hunter 23.5
1997 Deale Maryland 24 Hunter 23.5
Length: 24'     Beam:  8'     Draft:  1.5'
Year: 1997
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Deale, Maryland
Asking: $9,000
Sailboat Added 07-Apr-2023  More Details

Hunter 255 25.5
Hunter 255 25.5
Length: 25.5'     Beam:  9'     Draft:  4.5''
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Chesapeake Bay, Maryland
Asking: $6,200
Sailboat Added 30-Mar-2023  More Details

Hunter 31
Hunter 31
Length: 31'     Beam:  10'     Draft:  5.3'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Arnold, Maryland
Asking: $10,000
Sailboat Added 25-Apr-2023  More Details

Mariner 39 Center Cockpit
1982 Solomons Maryland 39 Mariner 39 Center Cockpit
Length: 39'     Beam:  11.7'     Draft:  5.5'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Solomons, Maryland
Asking: $17,000
Sailboat Added 19-Mar-2023  More Details

Whitby Whitby 42
Whitby Whitby 42
Length: 42'     Beam:  13'
Year: 1972
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: annapolis, Maryland
Asking: $5,000
Sailboat Added 18-Mar-2023  More Details

Precision Boatworks Precision 21
1991 Pasadena Maryland 21' Precision Boatworks Precision 21
Length: 21''     Beam:  8'3'     Draft:  1'9'
Year: 1991
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Pasadena, Maryland
Asking: $4,000
Sailboat Added 14-Mar-2023  More Details



Cape Dory Cape Dory 27
1982 Solomons Maryland 27 Cape Dory Cape Dory 27
Length: 27'     Beam:  8.5'     Draft:  4'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Solomons, Maryland
Asking: $20,000
Sailboat Added 08-Feb-2023  More Details

Laser XD
2009 Annapolis Maryland  Laser XD
Length: '
Year: 2009
Type: dinghy
Hull: fiberglass  monohull
Location: Annapolis, Maryland
Asking: $6,200
Sailboat Added 06-Feb-2023  More Details

Passport Passport Vista 545 CC
2018 Annapolis Maryland 54.5 Passport Passport Vista 545 CC
Length: 54.5'     Beam:  15.2'     Draft:  5.6'
Year: 2018
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Annapolis, Maryland
Asking: $690,000
Sailboat Added 27-Jan-2023  More Details


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