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Sailboats for Sale in Massachusetts - Discover the Sailboat of Your Dreams, or sell your current Massachusetts Sailboat to get ready for a new adventure today.
Your search returned 590 matches of 110339 sailboats posted to date

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1997 Custom Dark Harbor 20
 Edgartown Massachusetts  1997 Custom Dark Harbor 20
Length: '
Type: racer
Hull: composite  monohull
Location: Edgartown, Massachusetts
Asking: $44,000
Sailboat Added 12-Oct-2025  More Details

Cabo Rico 42
2005 Westport Massachusetts 46 Cabo Rico 42
Length: 46'     Beam:  12'8'     Draft:  5'3'
Year: 2005
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Westport, Massachusetts
Asking: $245,000
Sailboat Added 02-Oct-2025  More Details

oday daysailer
1966 Weymouth Massachusetts 17 oday daysailer
Length: 17'     Beam:  5'
Year: 1966
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Weymouth, Massachusetts
Asking: $1,500
Sailboat Added 27-Sep-2025  More Details



TPI J 24
2012 Boston Massachusetts 24 TPI J 24
Length: 24'     Beam:  9'     Draft:  4'
Year: 2012
Type: racer
Hull: fiberglass  monohull
Engine: gas outboard
Location: Boston, Massachusetts
Asking: $25,000
Sailboat Added 24-Sep-2025  More Details

Marshall Marine Marshall 22
1987 Duxbury Massachusetts 22 Marshall Marine Marshall 22
Length: 22'     Beam:  10'     Draft:  2 5'
Year: 1987
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Duxbury, Massachusetts
Asking: $16,000
Sailboat Added 23-Sep-2025  More Details

Featured Sailboat:  Aphrodite 101
1978 Marblehead Massachusetts 33 Aphrodite 101
Length: 33'     Beam:  8'     Draft:  5.4'
Year: 1978
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Marblehead, Massachusetts
Asking: $10,500
Featured Sailboat Added 22-Sep-2025  More Details

Pearson Sloop
Pearson Sloop
Length: 32'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Yarmouth, Massachusetts
Asking: $6,900
Sailboat Added 16-Sep-2025  More Details

Home made Fenwick-William
1982 Somerset Massachusetts 22 Home made Fenwick-William
Length: 22'     Beam:  10'     Draft:  2'
Year: 1982
Type: cruiser
Hull: composite  monohull
Engine: 1 diesel inboard
Location: Somerset, Massachusetts
Asking: $5,000
Sailboat Added 11-Sep-2025  More Details

Shannon Shannon 38 Cutter
1984 Marblehead Massachusetts 38 Shannon Shannon 38 Cutter
Length: 38'     Beam:  11' 6'     Draft:  5'
Year: 1984
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Marblehead, Massachusetts
Asking: $59,000
Sailboat Added 01-Sep-2025  More Details



Ericson 35-3
1985 SCITUATE Massachusetts 35.5 Ericson 35-3
Length: 35.5'     Beam:  11.4'     Draft:  6.1'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: SCITUATE, Massachusetts
Asking: $10,000
Sailboat Added 27-Aug-2025  More Details

1977 Marshall 22' Catboat
 Mattapoisett Massachusetts  1977 Marshall 22' Catboat
Length: '
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Mattapoisett, Massachusetts
Asking: $17,900
Sailboat Added 27-Aug-2025  More Details

1965 33' Friendship Sloop
1965  33'  Friendship Sloop
Length: '
Type: cruiser
Hull: wood  monohull
Engine: 1 diesel inboard
Location: Mattapoisett, Massachusetts
Asking: $38,500
Sailboat Added 27-Aug-2025  More Details

1977 24' Atlantic City Catboat
1977 Edgartown Massachusetts 24 1977 24'  Atlantic City Catboat
Length: 24'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Edgartown, Massachusetts
Asking: $60,000
Sailboat Added 27-Aug-2025  More Details

Featured Sailboat:  Hunter 146
2005 Concord Massachusetts 14.5 Hunter 146
Length: 14.5'     Beam:  5.8'     Draft:  0.5'
Year: 2005
Type: daysailer
Hull: composite  monohull
Location: Concord, Massachusetts
Asking: $4,000
Featured Sailboat Added 01-Sep-2025  More Details

Catalina 320
1994 Beverly Massachusetts 32 Catalina 320
Length: 32'     Beam:  11.6'     Draft:  4.25'
Year: 1994
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Beverly, Massachusetts
Asking: $42,500
Sailboat Added 13-Aug-2025  More Details

Beetle Beetlecat 12
Length: 12'     Beam:  6'     Draft:  1'
Year: 1984
Type: cruiser
Hull: wood  monohull
Location: Abington, Massachusetts
Asking: $1,800
Sailboat Added 04-Aug-2025  More Details

Atlantic City Catboat
1977 Edgartown Massachusetts 24  Atlantic City Catboat
Length: 24'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Edgartown, Massachusetts
Asking: $60,000
Sailboat Added 03-Aug-2025  More Details

Precision P14
1984 marblehead Massachusetts 14 Precision P14
Length: 14'     Beam:  6'     Draft:  1'
Year: 1984
Type: dinghy
Hull: fiberglass  monohull
Location: marblehead, Massachusetts
Asking: $2,400
Sailboat Added 02-Aug-2025  More Details

WINNER Opti
2010 Scituate Massachusetts 8 WINNER Opti
Length: 8'     Beam:  4'     Draft:  3'
Year: 2010
Type: dinghy
Hull: fiberglass  monohull
Location: Scituate, Massachusetts
Asking: $3,200
Sailboat Added 23-Jul-2025  More Details



Opti McLaughlin Pro Racer
2010 Scituate Massachusetts 8 Opti McLaughlin Pro Racer
Length: 8'     Beam:  4'     Draft:  1'
Year: 2010
Type: dinghy
Hull: fiberglass  monohull
Location: Scituate, Massachusetts
Asking: $3,200
Sailboat Added 22-Jul-2025  More Details

Catalina Catalina 30 Tall Rig
Length: 30'     Beam:  10'     Draft:  5'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Beverly Harbor SWYC, Massachusetts
Asking: $15,000
Sailboat Added 21-Jul-2025  More Details

Flying scot Flying Scot
Length: 19'     Beam:  6.75'     Draft:  4'
Year: 1987
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: gas inboard
Location: Duxbury, Massachusetts
Asking: $9,500
Sailboat Added 21-Jul-2025  More Details

Nacra 500
Nacra 500
Length: 15.5'     Beam:  8'
Year: 2005
Type: daysailer
Hull: fiberglass  monohull
Location: Ipswich, Massachusetts
Asking: $4,000
Sailboat Added 21-Jul-2025  More Details

O'Day Outlaw
1969 Gloucester Massachusetts 26 O'Day Outlaw
Length: 26'     Beam:  8'     Draft:  4'6'
Year: 1969
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Gloucester, Massachusetts
Asking: $1,200
Sailboat Added 21-Jul-2025  More Details

Precision P14
1984 Marblehead Massachusetts 14 Precision P14
Length: 14'     Beam:  6'     Draft:  1-2.5'
Year: 1984
Type: daysailer
Hull: fiberglass  monohull
Engine: 0 other inboard
Location: Marblehead, Massachusetts
Asking: $2,150
Sailboat Added 19-Jul-2025  More Details

1965 33' Friendship Sloop
 Mattapoisett Massachusetts  1965 33' Friendship Sloop
Length: '
Type: cruiser
Hull: wood  monohull
Engine: diesel inboard
Location: Mattapoisett, Massachusetts
Asking: $38,500
Sailboat Added 18-Jul-2025  More Details

Hutchins Com-Pac Picnic Cat
Hutchins Com-Pac Picnic Cat
Length: 14'     Beam:  66'
Year: 2008
Type: daysailer
Hull: fiberglass  monohull
Location: Pittsfield, Massachusetts
Asking: $13,000
Sailboat Added 17-Jul-2025  More Details

Crawford Melonseed Skiff
2001 Hopkinton Massachusetts 13.6 Crawford Melonseed Skiff
Length: 13.6'     Beam:  4.2'     Draft:  0.5'
Year: 2001
Type: daysailer
Hull: fiberglass  monohull
Location: Hopkinton, Massachusetts
Asking: $6,800
Sailboat Added 16-Jul-2025  More Details

1977 22' MARSHALL CATBOAT
1977 22' MARSHALL CATBOAT
Length: '
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mattapoisett, Massachusetts
Asking: $17,900
Sailboat Added 13-Jul-2025  More Details

Colgate 26
2002 Marion Massachusetts 26 Colgate 26
Length: 26'     Beam:  8.5'     Draft:  4.5'
Year: 2002
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Marion, Massachusetts
Asking: $22,500
Sailboat Added 13-Jul-2025  More Details

American 14-6
Length: 14.5'     Beam:  6'2"'     Draft:  .5'
Year: 2014
Type: daysailer
Hull: fiberglass  monohull
Engine: gas inboard
Location: West Dennis, Massachusetts
Asking: $3,500
Sailboat Added 11-Jul-2025  More Details



Willard Boat Works Arthur Wycoff
1962 Pocasset Massachusetts 37 Willard Boat Works Arthur Wycoff
Length: 37'     Beam:  12'     Draft:  6'
Year: 1962
Type: cruiser
Hull: wood  monohull
Engine: 1 diesel inboard
Location: Pocasset, Massachusetts
Asking: $20,000
Sailboat Added 01-Aug-2025  More Details

Ericson 34-2
1988 Salisbury Massachusetts 34 Ericson 34-2
Length: 34'     Beam:  11'     Draft:  62'
Year: 1988
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Salisbury, Massachusetts
Asking: $24,900
Sailboat Added 02-Jul-2025  More Details

Laser Standard
 Chilmark Massachusetts 14 Laser Standard
Length: 14'
Hull: fiberglass  monohull
Location: Chilmark, Massachusetts
Asking: $4,800
Sailboat Added 30-Jun-2025  More Details

Heard 28 Gaff Cutter
1997 Safe Harbour Hawthorne Cove Massachusetts 28 Heard 28 Gaff Cutter
Length: 28'     Beam:  10'     Draft:  5'
Year: 1997
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Safe Harbour Hawthorne Cove, Massachusetts
Asking: $59,000
Sailboat Added 26-Jun-2025  More Details

Catalina 36 MkII
2003 Salem Massachusetts 36 Catalina 36 MkII
Length: 36'     Beam:  11'11'     Draft:  4'5'
Year: 2003
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Salem, Massachusetts
Asking: $81,900
Sailboat Added 25-Jun-2025  More Details

Pearson Pearson 26' Triton
1970 Hingham Massachusetts 26 Pearson Pearson 26' Triton
Length: 26'     Beam:  8.5'     Draft:  4'
Year: 1970
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Hingham, Massachusetts
Asking: $5,000
Sailboat Added 23-Jun-2025  More Details

Laser
Laser
Length: 14'
Year: 1974
Type: daysailer
Hull: fiberglass  monohull
Location: Chatham, Massachusetts
Asking: $1,000
Sailboat Added 22-Jun-2025  More Details

Nacra 500
Nacra 500
Length: 16.5'     Beam:  8'
Year: 2005
Type: daysailer
Hull: fiberglass  catamaran
Engine: gas inboard
Location: Ipswich, Massachusetts
Asking: $7,000
Sailboat Added 17-Jun-2025  More Details

Catalina 38 Sparkman Stevens
1984 Boston Massachusetts 38 Catalina 38 Sparkman Stevens
Length: 38'     Beam:  12'     Draft:  6.8'
Year: 1984
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Boston, Massachusetts
Asking: $35,000
Sailboat Added 18-Jun-2025  More Details

Goat Island Skiff Row and Sail
Goat Island Skiff Row and Sail
Length: 16'
Type: other
Hull: wood  monohull
Engine: gas inboard
Location: Barnstable, Massachusetts
Asking: $6,500
Sailboat Added 28-May-2025  More Details

Allied Mistress Great cabin model
1973 Cape Cod Massachusetts 39'7
Length: 39'7"'     Beam:  12'     Draft:  4.0'
Year: 1973
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Cape Cod, Massachusetts
Asking: $7,500
Sailboat Added 26-May-2025  More Details

Endeavour 32
1979  Massachusetts 32 Endeavour 32
Length: 32'     Beam:  10'     Draft:  4.2'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Asking: $15,000
Sailboat Added 09-Jun-2025  More Details

Ranger Ranger 28TM
1976 South Dartmouth Massachusetts 28 Ranger Ranger 28TM
Length: 28'     Beam:  10'     Draft:  5'
Year: 1976
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: South Dartmouth, Massachusetts
Asking: $9,500
Sailboat Added 16-May-2025  More Details

Hinckley Ted Hood design
1977 Falmouth Massachusetts 43 Hinckley Ted Hood design
Length: 43'     Beam:  11'     Draft:  4 8'
Year: 1977
Type: other
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Falmouth, Massachusetts
Asking: $80,000
Sailboat Added 15-May-2025  More Details

Hobie 18
 Dracut Massachusetts 18 Hobie 18
Length: 18'
Type: racer/cruiser
Hull: other  monohull
Engine: gas inboard
Location: Dracut, Massachusetts
Asking: $375
Sailboat Added 11-May-2025  More Details

Marshall Sandigling
 Boxborough Massachusetts 15 Marshall Sandigling
Length: 15'     Draft:  3'
Type: other
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Boxborough, Massachusetts
Asking: $1,700,000
Sailboat Added 04-May-2025  More Details

Melges 24
1994 Boston Massachusetts 24 Melges 24
Length: 24'     Beam:  8.2'     Draft:  5'
Year: 1994
Type: racer
Hull: fiberglass  monohull
Engine: other outboard
Location: Boston, Massachusetts
Asking: $17,900
Sailboat Added 28-Apr-2025  More Details

Whitby 42 Ketch
1984 Boston Massachusetts 42 Whitby 42 Ketch
Length: 42'     Beam:  13'     Draft:  5'
Year: 1984
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Boston, Massachusetts
Asking: $44,900
Sailboat Added 25-Apr-2025  More Details

Catalina Yachts C30
Catalina Yachts C30
Length: 30'     Beam:  10 7'     Draft:  3.5'
Year: 1989
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: salem, Massachusetts
Asking: $26,900
Sailboat Added 22-Apr-2025  More Details

Fulcrum Speedworks UFO
2018 Marion Massachusetts 10.5 Fulcrum Speedworks UFO
Length: 10.5'     Beam:  5.6'     Draft:  3'
Year: 2018
Type: dinghy
Hull: fiberglass  catamaran
Location: Marion, Massachusetts
Asking: $5,500
Sailboat Added 21-Apr-2025  More Details

AlcortAMC Flying Fish
1972 Northampton Massachusetts 14 AlcortAMC Flying Fish
Length: 14'     Beam:  5.67'     Draft:  2.83'
Year: 1972
Type: cruiser
Hull: fiberglass  monohull
Location: Northampton, Massachusetts
Asking: $1,100
Sailboat Added 14-Apr-2025  More Details

Bristol Hood
1979 Salem Massachusetts 32 Bristol Hood
Length: 32'     Beam:  9.5'     Draft:  4.5'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Salem, Massachusetts
Asking: $26,000
Sailboat Added 12-Apr-2025  More Details

Custom cruising cutter Morgan design Irwin built
1979 Gloucester Massachusetts 44.5 Custom cruising cutter Morgan design Irwin built
Length: 44.5'     Beam:  11'     Draft:  6.5'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Gloucester, Massachusetts
Asking: $25,000
Sailboat Added 30-Mar-2025  More Details

Catalina 320 Wing Keel
1994 Winthrop Massachusetts 32 Catalina 320 Wing Keel
Length: 32'     Beam:  11.75'     Draft:  4.25'
Year: 1994
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Winthrop, Massachusetts
Asking: $42,500
Sailboat Added 25-Apr-2025  More Details

S2 7.9
1984 Beverly Massachusetts 26 S2 7.9
Length: 26'     Beam:  9'     Draft:  5'
Year: 1984
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Beverly, Massachusetts
Asking: $14,000
Sailboat Added 20-Mar-2025  More Details

Bristol Corinthian
1965 Gloucester Massachusetts 19 Bristol Corinthian
Length: 19'     Beam:  6.5'     Draft:  2.75'
Year: 1965
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Gloucester, Massachusetts
Asking: $2,800
Sailboat Added 18-Mar-2025  More Details

C&C 37R
1989 Marion Massachusetts 37 C&C 37R
Length: 37'     Beam:  12.7'     Draft:  8'
Year: 1989
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Marion, Massachusetts
Asking: $77,000
Sailboat Added 15-Mar-2025  More Details

Catalina 30 MKII
Catalina 30 MKII
Length: 30'     Beam:  11'     Draft:  3.10'
Year: 1989
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Hyannis, Massachusetts
Asking: $9,700
Sailboat Added 25-Feb-2025  More Details

Cape Cod Shipbuilding Bullseye
1965 Cataumet Massachusetts 16 Cape Cod Shipbuilding Bullseye
Length: 16'
Year: 1965
Type: daysailer
Hull: fiberglass  monohull
Engine: gas inboard
Location: Cataumet, Massachusetts
Asking: $12,000
Sailboat Added 18-Feb-2025  More Details



Kaiser Gale Force 34
1978 Mattapoisett Massachusetts 39 Kaiser Gale Force 34
Length: 39'     Beam:  10'     Draft:  5.3'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mattapoisett, Massachusetts
Asking: $29,000
Sailboat Added 03-Jan-2025  More Details

Ericson 30 plus
1985 Lynn Massachusetts 30 Ericson 30 plus
Length: 30'     Beam:  10'     Draft:  4.5'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Lynn, Massachusetts
Asking: $10,000
Sailboat Added 01-Jan-2025  More Details

Ovington 29er
2016 Falmouth MA Massachusetts  Ovington 29er
Length: '
Year: 2016
Type: dinghy
Hull: fiberglass  monohull
Engine: gas inboard
Location: Falmouth MA, Massachusetts
Asking: $5,000
Sailboat Added 21-Dec-2024  More Details


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