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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 592 matches of 109924 sailboats posted to date

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Passamaquoddy Passamaquoddy 22
 Marthas Vineyard Massachusetts 22 Passamaquoddy Passamaquoddy 22
Length: 22'     Beam:  8'     Draft:  4.5'
Type: daysailer
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Marthas Vineyard, Massachusetts
Asking: $9,000
Sailboat Added 12-Oct-2024  More Details

Tartan 34c
1976 Winthrop Massachusetts 34' Tartan 34c
Length: 34''     Beam:  10''     Draft:  4''
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Winthrop, Massachusetts
Asking: $15,000
Sailboat Added 15-Mar-2025  More Details

Edey and Duff Herreshoff 12 12 Doughdish
1983 Marthas Vineyard Massachusetts 16 Edey and Duff   Herreshoff 12 12 Doughdish
Length: 16'     Beam:  5.8'     Draft:  2.5'
Year: 1983
Type: daysailer
Hull: fiberglass  monohull
Location: Marthas Vineyard, Massachusetts
Asking: $40,000
Sailboat Added 03-Oct-2024  More Details



Herreshoff Rozinante Ketch
1963 South Dartmouth Massachusetts 38 Herreshoff Rozinante Ketch
Length: 38'
Year: 1963
Hull: fiberglass  
Location: South Dartmouth, Massachusetts
Asking: $39,500
Sailboat Added 27-Sep-2024  More Details

AMEL 50
AMEL 50
Length: 50'     Beam:  15.8'     Draft:  7'
Year: 2019
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Boston, Massachusetts
Asking: $1,000,000
Sailboat Added 11-Sep-2024  More Details

O'Day 35
O'Day 35
Length: 35'     Beam:  11'3'     Draft:  5'6'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Boston, Massachusetts
Asking: $34,950
Sailboat Added 11-Sep-2024  More Details

Allied Seawind
1972 Danvers Massachusetts 30 Allied Seawind
Length: 30'     Beam:  8.5'     Draft:  4.5'
Year: 1972
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Danvers, Massachusetts
Asking: $12,000
Sailboat Added 07-Sep-2024  More Details

Bristol Yachts Bristol Corinthian 19
1967 Pocasset Massachusetts 19.6' Bristol Yachts Bristol Corinthian 19
Length: 19.6''     Beam:  6'6'     Draft:  2'9'
Year: 1967
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Pocasset, Massachusetts
Asking: $2,250
Sailboat Added 13-Sep-2024  More Details

Pearson Ariel sloop
1968 Cataumet Massachusetts 27 Pearson Ariel sloop
Length: 27'     Beam:  10'     Draft:  3'
Year: 1968
Type: daysailer
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Cataumet, Massachusetts
Asking: $12,000
Sailboat Added 30-Aug-2024  More Details



Freedom 21 Tillotson Pearson Freedom 21
1985 COHASSET Massachusetts 21 Freedom 21 Tillotson Pearson Freedom 21
Length: 21'     Beam:  8'     Draft:  3.8'
Year: 1985
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: COHASSET, Massachusetts
Asking: $4,900
Sailboat Added 28-Aug-2024  More Details

The Landing School 16 Haven 12-1/2 Class Sloop Sailboat
2001 Chilmark Massachusetts 16 The Landing School 16 Haven 12-1/2 Class Sloop Sailboat
Length: 16'     Beam:  6'1'     Draft:  18'
Year: 2001
Type: daysailer
Hull: wood  monohull
Engine: 0 gas inboard
Location: Chilmark, Massachusetts
Asking: $28,000
Sailboat Added 20-Aug-2024  More Details

Pacific Seacraft Crealock 37
1985 New Bedford Massachusetts 37 Pacific Seacraft Crealock 37
Length: 37'     Beam:  11'     Draft:  5.5'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: New Bedford, Massachusetts
Asking: $54,999
Sailboat Added 19-Aug-2024  More Details

O'Donnel AC Cat
O'Donnel AC Cat
Length: 24'     Beam:  11'     Draft:  2.5'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Cohasset, Massachusetts
Asking: $47,500
Sailboat Added 18-Aug-2024  More Details

Chesapeake light craft Peapod
2024 Marshfield Massachusetts 136 Chesapeake light craft Peapod
Length: 136'
Year: 2024
Type: daysailer
Hull: other  monohull
Engine: gas inboard
Location: Marshfield, Massachusetts
Asking: $6,500
Sailboat Added 15-Aug-2024  More Details

O'Day Rhodes 19
O'Day Rhodes 19
Length: 19'
Year: 1976
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Barnstable, Massachusetts
Asking: $4,500
Sailboat Added 13-Aug-2024  More Details

McLaughlin
Length: '
Year: 2021
Type: racer
Hull: fiberglass  monohull
Location: Wild Harbor Yacht Club North Falmouth, Massachusetts
Asking: $2,900
Sailboat Added 11-Aug-2024  More Details

Vanguard 15
1996 Edgartown Massachusetts 15.25 Vanguard 15
Length: 15.25'     Beam:  5.5'     Draft:  3.42'
Year: 1996
Type: dinghy
Hull: fiberglass  monohull
Location: Edgartown, Massachusetts
Asking: $2,500
Sailboat Added 29-Jul-2024  More Details

O'Day Rhodes 19
60 Edgartown Massachusetts 19 O'Day Rhodes 19
Length: 19'     Beam:  7'     Draft:  3.25'
Year: 60
Type: daysailer
Hull: fiberglass  monohull
Location: Edgartown, Massachusetts
Asking: $1,200
Sailboat Added 23-Jun-2024  More Details

Pearson 365
1976 Hull Massachusetts 36.5 Pearson 365
Length: 36.5'     Beam:  11.42'     Draft:  4.5'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Hull, Massachusetts
Asking: $16,000
Sailboat Added 21-Jun-2024  More Details



Chrysler C20
1978 Falmouth Massachusetts 20 Chrysler C20
Length: 20'     Beam:  6'     Draft:  2'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Location: Falmouth, Massachusetts
Asking: $1,750
Sailboat Added 30-May-2024  More Details

Catalina 30 MKIII
1995 south shore Massachusetts 30 Catalina 30 MKIII
Length: 30'     Beam:  10'     Draft:  4'
Year: 1995
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: south shore, Massachusetts
Asking: $3,000
Sailboat Added 21-May-2024  More Details

Cape Cod Shipbuilding Bullseye
1971 Marion Massachusetts 15.7 Cape Cod Shipbuilding Bullseye
Length: 15.7'     Beam:  5.8'     Draft:  2.5'
Year: 1971
Type: dinghy
Hull: fiberglass  monohull
Location: Marion, Massachusetts
Asking: $9,000
Sailboat Added 17-May-2024  More Details

Frers 42 Custom
1977 Sterling Massachusetts Massachusetts 42 Frers 42 Custom
Length: 42'     Beam:  13'     Draft:  6'
Year: 1977
Type: racer/cruiser
Hull: aluminum  monohull
Engine: 1 diesel inboard
Location: Sterling Massachusetts, Massachusetts
Asking: $9,900
Sailboat Added 16-May-2024  More Details

Catalina 28MK II
1998 Marblehead Massachusetts 28 Catalina 28MK II
Length: 28'     Beam:  10'4'     Draft:  3'8'
Year: 1998
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Marblehead, Massachusetts
Asking: $35,000
Sailboat Added 17-May-2024  More Details

Bristol Sailstar 26
1973 East Boston Massachusetts 26 Bristol Sailstar 26
Length: 26'     Beam:  8'     Draft:  3.82'
Year: 1973
Type: cruiser
Hull: fiberglass  monohull
Engine: gas outboard
Location: East Boston, Massachusetts
Asking: $4,500
Sailboat Added 06-May-2024  More Details

Heavenly Twin SOLD Heavenly Twin 26 Catamaran
1977 Mattapoisett Massachusetts 26 Heavenly Twin SOLD Heavenly Twin 26 Catamaran
Length: 26'     Beam:  12.5'     Draft:  2.2'
Year: 1977
Type: cruiser
Hull: fiberglass  catamaran
Engine: 2 diesel inboard
Location: Mattapoisett, Massachusetts
Asking: $8,300
Sailboat Added 04-May-2024  More Details

Catalina Swing Keel
1984 217 Old Oaken Bucket Rd  Norwell Massachusetts 25 Catalina Swing Keel
Length: 25'     Beam:  8''     Draft:  3'-5''
Year: 1984
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: 217 Old Oaken Bucket Rd Norwell, Massachusetts
Asking: $1,000
Sailboat Added 03-May-2024  More Details

Sabre Sloop 28
Length: 28'     Beam:  9.2'     Draft:  4.5'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Hull, Massachusetts
Asking: $8,500
Sailboat Added 01-May-2024  More Details

Hobiecat 18
1984 Cape Cod Massachusetts 18 Hobiecat 18
Length: 18'     Beam:  8'     Draft:  1'
Year: 1984
Type: other
Hull: fiberglass  catamaran
Location: Cape Cod, Massachusetts
Asking: $2,000
Sailboat Added 22-Apr-2024  More Details

Pearson 10M
Pearson 10M
Length: 33'     Beam:  11'     Draft:  6'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Fall River, Massachusetts
Asking: $12,000
Sailboat Added 11-Apr-2024  More Details

J Boats 24
 Marblehead Massachusetts 24 J Boats 24
Length: 24'     Beam:  7'     Draft:  4.5'
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: gas inboard
Location: Marblehead, Massachusetts
Asking: $12,500
Sailboat Added 16-Aug-2024  More Details



Soverel 28
1963 Wareham Massachusetts 28 Soverel 28
Length: 28'     Beam:  8.33'     Draft:  4.5'
Year: 1963
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Wareham, Massachusetts
Asking: $1,000
Sailboat Added 25-Mar-2024  More Details

Bristol 40
1972 Salem Massachusetts 40 Bristol 40
Length: 40'     Beam:  10'9'     Draft:  4''
Year: 1972
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Salem, Massachusetts
Asking: $39,500
Sailboat Added 19-Mar-2024  More Details

Alden Lecompte Malabar Sr
1957 Marthas Vineyard Massachusetts 33.5 Alden Lecompte Malabar Sr
Length: 33.5'     Beam:  9.5'     Draft:  5.5'
Year: 1957
Type: cruiser
Hull: wood  monohull
Engine: 1 diesel inboard
Location: Marthas Vineyard, Massachusetts
Asking: $15,000
Sailboat Added 17-Mar-2024  More Details

Pearson Pearson 35
1975 Mattapoisett Massachusetts 35 Pearson Pearson 35
Length: 35'     Beam:  10'     Draft:  3'9'
Year: 1975
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Mattapoisett, Massachusetts
Asking: $19,900
Sailboat Added 16-Mar-2024  More Details

Morgan 462
1981 East Dennis Massachusetts 46 Morgan 462
Length: 46'     Beam:  13'     Draft:  5.6'
Year: 1981
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: East Dennis, Massachusetts
Asking: $42,000
Sailboat Added 21-Feb-2024  More Details

Bristol 43.3
1990 South of Boston Massachusetts 43 Bristol 43.3
Length: 43'     Beam:  13'     Draft:  4.5'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: South of Boston, Massachusetts
Asking: $148,000
Sailboat Added 27-Jan-2024  More Details

Allan White and Son Englyn
1960 Vineyard Haven Massachusetts 26 Allan White and Son Englyn
Length: 26'     Beam:  8'     Draft:  5'
Year: 1960
Type: cruiser
Hull: wood  monohull
Engine: 1 diesel inboard
Location: Vineyard Haven, Massachusetts
Asking: $22,000
Sailboat Added 18-Jan-2024  More Details

Mirror Dinghy 31578
 Fairhaven Massachusetts 10.82 Mirror Dinghy 31578
Length: 10.82'     Beam:  4.58'     Draft:  2.33'
Type: dinghy
Hull: wood  monohull
Location: Fairhaven, Massachusetts
Asking: $2,500
Sailboat Added 01-Jan-2024  More Details

Crosby Wianno Sr / Gaff Rigged Knockabout Sloop
1972 Oak Bluffs Massachusetts 25  Crosby Wianno Sr / Gaff Rigged Knockabout Sloop
Length: 25'
Year: 1972
Type: racer
Hull: wood  monohull
Location: Oak Bluffs, Massachusetts
Asking: $15,000
Sailboat Added 03-Dec-2023  More Details

Catalina 36 MKII
2005 Cape Cod Massachusetts 36 Catalina 36 MKII
Length: 36'     Beam:  12'     Draft:  5.8'
Year: 2005
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Cape Cod, Massachusetts
Asking: $110,000
Sailboat Added 23-Nov-2023  More Details

Menger Catboat
Menger Catboat
Length: 19'
Year: 1996
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Hinghman, Massachusetts
Asking: $25,000
Sailboat Added 31-Oct-2023  More Details

Cape Dory CD14
Cape Dory CD14
Length: 14'6'     Beam:  51'     Draft:  6'
Year: 1972
Type: daysailer
Hull: fiberglass  monohull
Engine: other outboard
Location: Marion, Massachusetts
Asking: $4,000
Sailboat Added 14-Oct-2023  More Details

Morgan 34
1966 Cape Cod Massachusetts 34 Morgan 34
Length: 34'     Beam:  10'     Draft:  3.25'
Year: 1966
Type: racer/cruiser
Hull: fiberglass  monohull
Location: Cape Cod, Massachusetts
Asking: $15,000
Sailboat Added 12-Oct-2023  More Details

Jeanneau Lagoon 380
2003 Provincetown Massachusetts 38 Jeanneau Lagoon 380
Length: 38'     Beam:  21.5'     Draft:  3.77'
Year: 2003
Type: daysailer
Hull: fiberglass  catamaran
Engine: 2 diesel inboard
Location: Provincetown, Massachusetts
Asking: $209,000
Sailboat Added 03-Oct-2023  More Details

Passamaquoddy Passamaquoddy 22
1974 oak bluffs Massachusetts 22 Passamaquoddy Passamaquoddy 22
Length: 22'     Beam:  8'     Draft:  4.5'
Year: 1974
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: oak bluffs, Massachusetts
Asking: $5,000
Sailboat Added 28-Sep-2023  More Details

Bennett Race Boats Viper 640
1997 Marblehead Massachusetts 21 Bennett Race Boats Viper 640
Length: 21'     Beam:  8'     Draft:  5'
Year: 1997
Type: racer
Hull: fiberglass  monohull
Location: Marblehead, Massachusetts
Asking: $8,500
Sailboat Added 11-Sep-2023  More Details

Corsair 27 324
1991 Boston area Massachusetts 27 Corsair 27 324
Length: 27'     Beam:  19.2'     Draft:  1.2''
Year: 1991
Type: daysailer
Hull: composite  trimaran
Engine: 1 gas outboard
Location: Boston area, Massachusetts
Asking: $37,500
Sailboat Added 04-Sep-2023  More Details

Marshall Sanderling
1975 Charlestown Massachusetts 18 Marshall Sanderling
Length: 18'     Beam:  9'     Draft:  4'
Year: 1975
Type: other
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Charlestown, Massachusetts
Asking: $12,500
Sailboat Added 02-Sep-2023  More Details

Load Rite trailer
1959 Hyannis MA Massachusetts  Load Rite trailer
Length: '
Year: 1959
Type: daysailer
Hull: wood  monohull
Engine: gas inboard
Location: Hyannis MA, Massachusetts
Sailboat Added 22-Aug-2023  More Details

C&C 33 Mk1
1976 Beverly MA Salem Sound Massachusetts 32.9 C&C 33 Mk1
Length: 32.9'     Beam:  10.5'     Draft:  5.5'
Year: 1976
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Beverly MA Salem Sound, Massachusetts
Asking: $15,900
Sailboat Added 11-Aug-2023  More Details

Legnos Mystic 20
1975 Harwich Port Massachusetts 20 Legnos Mystic 20
Length: 20'     Beam:  8'     Draft:  2'
Year: 1975
Type: daysailer
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Harwich Port, Massachusetts
Asking: $18,000
Sailboat Added 04-Aug-2023  More Details

Stuart Rhodes 19 Centerboard
1992 Cape Cod Massachusetts 19 Stuart Rhodes 19 Centerboard
Length: 19'     Beam:  7'     Draft:  3.3'
Year: 1992
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Cape Cod, Massachusetts
Asking: $18,000
Sailboat Added 25-Jul-2023  More Details

Beneteau Oceanis 400
1994 Boston Massachusetts 40 Beneteau Oceanis 400
Length: 40'     Beam:  13'     Draft:  5.5'
Year: 1994
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Boston, Massachusetts
Asking: $110,000
Sailboat Added 19-Jul-2023  More Details

C&C 32
1984 Mattapoisett Massachusetts 31.5 C&C 32
Length: 31.5'     Beam:  10.25'     Draft:  5.67'
Year: 1984
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mattapoisett, Massachusetts
Asking: $25,000
Sailboat Added 06-Jul-2023  More Details

Mirage Yachts M33
Mirage Yachts M33
Length: 33.5'     Beam:  11.5'     Draft:  5'
Year: 1982
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: New Bedford, Massachusetts
Asking: $24,900
Sailboat Added 05-Jul-2023  More Details

Topaz Topper Race 3.2
2019 Littleton Massachusetts 11.2 Topaz Topper Race 3.2
Length: 11.2'     Beam:  3.9'
Year: 2019
Type: dinghy
Hull: other  monohull
Location: Littleton, Massachusetts
Asking: $3,500
Sailboat Added 10-Jun-2023  More Details

Dyer Boats The Anchorage Dyer Dhow
1954 Scituate Massachusetts 9 Dyer Boats The Anchorage Dyer Dhow
Length: 9'     Beam:  4.5'     Draft:  1'
Year: 1954
Type: dinghy
Hull: fiberglass  monohull
Engine: other inboard
Location: Scituate, Massachusetts
Asking: $4,500
Sailboat Added 05-Jun-2023  More Details

Bristol 27
1967 Mattapoisett Massachusetts 27 Bristol 27
Length: 27'     Beam:  8'     Draft:  4'
Year: 1967
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Mattapoisett, Massachusetts
Asking: $6,000
Sailboat Added 22-May-2023  More Details

Pearson 303
1983 Marion Massachusetts 30 Pearson 303
Length: 30'     Beam:  11'     Draft:  4'4'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Marion, Massachusetts
Asking: $25,900
Sailboat Added 09-May-2023  More Details

Cape Cod Shipbuilding Mercury
  Massachusetts 15 Cape Cod Shipbuilding Mercury
Length: 15'     Beam:  5.5'     Draft:  1'
Type: daysailer
Hull: fiberglass  monohull
Engine: gas inboard
Asking: $3,500
Sailboat Added 05-May-2023  More Details

Talman Yachts Menemsha 24
1971 East Falmouth Massachusetts 24 Talman Yachts Menemsha 24
Length: 24'     Beam:  8'     Draft:  2'6'
Year: 1971
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: East Falmouth, Massachusetts
Asking: $7,000
Sailboat Added 04-May-2023  More Details

Warren Mutihull Designs Warren 27
1991 Salem Massachusetts 29 Warren Mutihull Designs Warren 27
Length: 29'     Beam:  27'     Draft:  2'
Year: 1991
Type: daysailer
Hull: other  trimaran
Engine: 1 gas outboard
Location: Salem, Massachusetts
Asking: $5,000
Sailboat Added 08-Jun-2023  More Details

O'Day O'Day 25
1979 North Falmouth Massachusetts 25 O'Day O'Day 25
Length: 25'     Beam:  15'     Draft:  6'
Year: 1979
Type: daysailer
Hull: fiberglass  monohull
Engine: 2 gas outboard
Location: North Falmouth, Massachusetts
Asking: $3,000
Sailboat Added 10-Apr-2023  More Details

Evelyn OD
Evelyn OD
Length: 26'     Beam:  9.5'     Draft:  4.5'
Year: 1979
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Beverly, Massachusetts
Asking: $7,900
Sailboat Added 08-May-2023  More Details

Allied Seawind
1972 Danvers MA Massachusetts 30 Allied Seawind
Length: 30'     Beam:  8.5'     Draft:  4.5'
Year: 1972
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Danvers MA, Massachusetts
Asking: $22,500
Sailboat Added 22-Mar-2023  More Details



Soveral 28
Soveral 28
Length: 28'     Beam:  8'     Draft:  4.5'
Year: 1966
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Fairhaven, Massachusetts
Asking: $1
Sailboat Added 20-Mar-2023  More Details

Ericson 30
Ericson 30
Length: 29.92'     Beam:  10.50'     Draft:  5.83'
Year: 1988
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Lynn, Massachusetts
Asking: $23,000
Sailboat Added 16-Mar-2023  More Details

Etchells 22
1980 Sandwich Massachusetts 33 Etchells 22
Length: 33'     Beam:  6'     Draft:  4.5'
Year: 1980
Type: daysailer
Hull: fiberglass  monohull
Engine: 0 gas inboard
Location: Sandwich, Massachusetts
Asking: $10,000
Sailboat Added 13-Mar-2023  More Details


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