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Sailboats for Sale in Connecticut - Discover the Sailboat of Your Dreams, or sell your current Connecticut Sailboat to get ready for a new adventure today.
Your search returned 427 matches of 110666 sailboats posted to date

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Simmons C420
2022  Connecticut 14 Simmons C420
Length: 14'     Beam:  5.5'
Year: 2022
Type: dinghy
Hull: fiberglass  monohull
Engine: gas inboard
Asking: $11,500
Sailboat Added 17-Nov-2025  More Details

1996 Menger 19' Catboat
1996 Menger 19'  Catboat
Length: '
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Noank, Connecticut
Asking: $12,900
Sailboat Added 26-Oct-2025  More Details

Catalina 42 Mark II
1999 Deep River Connecticut 42 Catalina 42 Mark II
Length: 42'     Beam:  13.8'     Draft:  5.0'
Year: 1999
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Deep River, Connecticut
Asking: $129,000
Sailboat Added 22-Oct-2025  More Details



Quickstep 24
1978 Milford Connecticut 24 Quickstep 24
Length: 24'     Beam:  8'     Draft:  3.5'
Year: 1978
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Milford, Connecticut
Asking: $6,500
Sailboat Added 21-Oct-2025  More Details

Featured Sailboat:  Edy & Duff Dovekie 21
1980 20 Godard Road            North Granby Connecticut 21'6 Edy & Duff Dovekie 21
Length: 21'6'     Beam:  6'6'     Draft:  4'
Year: 1980
Type: daysailer
Hull: fiberglass  monohull
Location: 20 Godard Road North Granby, Connecticut
Asking: $3,500
Featured Sailboat Added 15-Oct-2025  More Details

J Boats J/22
1985 Clinton CT Connecticut 22 J Boats J/22
Length: 22'     Beam:  8'     Draft:  4'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Clinton CT, Connecticut
Asking: $6,500
Sailboat Added 14-Oct-2025  More Details

Robertson & Caine Leopard 38
1999 New London Connecticut 38 Robertson & Caine Leopard 38
Length: 38'     Beam:  21'     Draft:  3.7'
Year: 1999
Type: motorsailer
Hull: fiberglass  catamaran
Engine: gas inboard
Location: New London, Connecticut
Asking: $180,000
Sailboat Added 11-Oct-2025  More Details

Hunter 420 Passagemaker
2001 Groton Connecticut 42 Hunter 420 Passagemaker
Length: 42'     Beam:  14'     Draft:  4.9'
Year: 2001
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Groton, Connecticut
Asking: $122,900
Sailboat Added 04-Oct-2025  More Details

Featured Sailboat:  Beneteau First 235
1989 Groton Connecticut 23.33 Beneteau First 235
Length: 23.33'     Beam:  8.17'     Draft:  2.75'
Year: 1989
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Groton, Connecticut
Asking: $8,500
Featured Sailboat Added 04-Oct-2025  More Details



Grampain classic 22'
1971 Fairfeild Connecticut 22 Grampain classic 22'
Length: 22'     Beam:  6'     Draft:  3.5'
Year: 1971
Type: daysailer
Hull: fiberglass  monohull
Engine: 0 other outboard
Location: Fairfeild, Connecticut
Asking: $5,600
Sailboat Added 29-Sep-2025  More Details

Nonsuch 30 Ultra
1985 Noank Connecticut 30 Nonsuch 30 Ultra
Length: 30'     Beam:  11.5'     Draft:  5'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Noank, Connecticut
Asking: $49,900
Sailboat Added 21-Sep-2025  More Details

Howard Boats Barnstable Cat Boat
2005 Riverside Connecticut 12 Howard Boats Barnstable Cat Boat
Length: 12'     Beam:  6'     Draft:  2'
Year: 2005
Type: daysailer
Hull: fiberglass  monohull
Location: Riverside, Connecticut
Asking: $6,000
Sailboat Added 30-Aug-2025  More Details

Ontario Boats sonar
1989 Shelton Connecticut 23 Ontario Boats sonar
Length: 23'     Beam:  7.8'     Draft:  4'
Year: 1989
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Shelton, Connecticut
Asking: $4,500
Sailboat Added 21-Aug-2025  More Details

Laser Performance Laser
2018 Stamford Connecticut 13 Laser Performance Laser
Length: 13'     Beam:  5'     Draft:  2'
Year: 2018
Type: dinghy
Hull: fiberglass  monohull
Engine: gas inboard
Location: Stamford, Connecticut
Asking: $6,250
Sailboat Added 19-Aug-2025  More Details

catalina 22
1986 Stamford Connecticut 22 catalina 22
Length: 22'     Beam:  8'
Year: 1986
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Stamford, Connecticut
Asking: $5,500
Sailboat Added 14-Aug-2025  More Details

Beneteau 36 CC Center Cockpit
2002 Noank Mystic Connecticut 36.5 Beneteau 36 CC Center Cockpit
Length: 36.5'     Beam:  12.5'     Draft:  5'
Year: 2002
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Noank Mystic, Connecticut
Asking: $85,000
Sailboat Added 12-Aug-2025  More Details

Pearson Pearson 26
1976 New London Connecticut 26 Pearson Pearson 26
Length: 26'     Beam:  8.69'     Draft:  4'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: New London, Connecticut
Asking: $4,000
Sailboat Added 09-Aug-2025  More Details

CSY Caribbean Sailing Yachts 44 Walkover Cutter
1977 Branford Connecticut 44 CSY Caribbean Sailing Yachts 44 Walkover Cutter
Length: 44'     Beam:  13.3'     Draft:  6.5'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Branford, Connecticut
Asking: $61,000
Sailboat Added 07-Aug-2025  More Details

Sturgis PS2000 C420
2018  Connecticut  Sturgis PS2000 C420
Length: '
Year: 2018
Type: dinghy
Hull: fiberglass  monohull
Asking: $8,000
Sailboat Added 05-Aug-2025  More Details



Flying Scot
1981 Fairfield Connecticut 19 Flying Scot
Length: 19'     Beam:  6.8'     Draft:  4.0'
Year: 1981
Type: dinghy
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Fairfield, Connecticut
Asking: $2,300
Sailboat Added 04-Aug-2025  More Details

Fusion Fusion 15
2002 Essex Connecticut 15.7 Fusion Fusion 15
Length: 15.7'     Beam:  5.5'     Draft:  0.4'
Year: 2002
Type: daysailer
Hull: fiberglass  monohull
Location: Essex, Connecticut
Asking: $4,000
Sailboat Added 25-Jul-2025  More Details

Freedom 35
1993 Mystic Connecticut 35 Freedom 35
Length: 35'     Beam:  12'     Draft:  4.5'
Year: 1993
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mystic, Connecticut
Asking: $55,000
Sailboat Added 17-Jul-2025  More Details

Hobie Getaway
Length: 16'
Year: 2015
Type: cruiser
Hull: other  monohull
Location: Colchester, Connecticut
Asking: $2,000
Sailboat Added 16-Jul-2025  More Details

Freedom 40/40
1995 Norwalk Connecticut 40 Freedom 40/40
Length: 40'     Beam:  13'     Draft:  6'
Year: 1995
Type: other
Hull: fiberglass  
Engine: 1 diesel inboard
Location: Norwalk, Connecticut
Asking: $119,500
Sailboat Added 15-Jul-2025  More Details

Menger Catboat
Menger Catboat
Length: 19'
Year: 1996
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Noank, Connecticut
Asking: $16,900
Sailboat Added 10-Jul-2025  More Details

Beneteau First 367
2005 Guilford Connecticut 36 Beneteau First 367
Length: 36'     Beam:  11.4'     Draft:  7.1'
Year: 2005
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Guilford, Connecticut
Asking: $69,900
Sailboat Added 12-Jun-2025  More Details

Hunter 40.5
1997 Stamford Connecticut 40 Hunter 40.5
Length: 40'     Beam:  13'     Draft:  4.9'
Year: 1997
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Stamford, Connecticut
Asking: $89,000
Sailboat Added 10-Jun-2025  More Details

Vanguard Laser
Length: 14'     Beam:  5'     Draft:  3'
Year: 2001
Type: dinghy
Hull: fiberglass  monohull
Location: Norwalk, Connecticut
Asking: $3,000
Sailboat Added 31-May-2025  More Details

C&C 27 Mark V
C&C 27 Mark V
Length: 27'     Beam:  9.16'     Draft:  4.25'
Year: 1984
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Old Greenwich, Connecticut
Asking: $3,500
Sailboat Added 19-May-2025  More Details

Hunter
Hunter
Length: 25.5'     Beam:  9'     Draft:  4.5'
Year: 1984
Type: daysailer
Hull: fiberglass  monohull
Engine: 0 gas outboard
Location: Norwalk, Connecticut
Asking: $3,900
Sailboat Added 18-May-2025  More Details

Cal 34-3
1977 Noank Connecticut 33.3 Cal 34-3
Length: 33.3'     Beam:  10'     Draft:  5'
Year: 1977
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Noank, Connecticut
Asking: $15,000
Sailboat Added 07-May-2025  More Details



Flying Scot Flying Scot
2002  Connecticut 19 Flying Scot Flying Scot
Length: 19'     Beam:  6'9'     Draft:  18'
Year: 2002
Type: racer/cruiser
Hull: fiberglass  monohull
Asking: $13,950
Sailboat Added 24-Apr-2025  More Details

Ericson 25
1983 Stratford CT Connecticut 25.5 Ericson 25
Length: 25.5'     Beam:  9.2'     Draft:  4.11'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Stratford CT, Connecticut
Asking: $2,000
Sailboat Added 15-Apr-2025  More Details

Pearson 26 Sloop
Length: 26'1"'     Beam:  8''     Draft:  4''
Year: 1973
Type: daysailer
Hull: fiberglass  monohull
Engine: gas outboard
Location: Portland, Connecticut
Asking: $2,000
Sailboat Added 03-Apr-2025  More Details

Ovington ILCA 7
2020 Greenwich Connecticut 14.75 Ovington ILCA 7
Length: 14.75'     Beam:  4.6'
Year: 2020
Type: racer
Hull: fiberglass  monohull
Location: Greenwich, Connecticut
Asking: $11,000
Sailboat Added 31-Mar-2025  More Details

Pearson 35
1976 Groton Connecticut 35 Pearson 35
Length: 35'     Beam:  10'     Draft:  4'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Groton, Connecticut
Asking: $18,500
Sailboat Added 29-Mar-2025  More Details

2 Original I420s 1 jib and mainsail 1 forward mast cat setup
Length: 13'.9'     Beam:  5'4'     Draft:  3''
Year: 1965
Type: dinghy
Hull: fiberglass  monohull
Location: Newtown, Connecticut
Asking: $2,000
Sailboat Added 17-Mar-2025  More Details

Hughs Columbia 87 Coastal Cruiser
1982 Haddam CT Connecticut 29.9 Hughs Columbia 87 Coastal Cruiser
Length: 29.9'     Beam:  10'     Draft:  4.5'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Haddam CT, Connecticut
Asking: $8,000
Sailboat Added 10-Mar-2025  More Details

Catalina C30 Mk II Tall Rig
1990 Mystic CT Connecticut 30 Catalina C30 Mk II Tall Rig
Length: 30'     Beam:  12'     Draft:  5'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Mystic CT, Connecticut
Asking: $30,000
Sailboat Added 27-Feb-2025  More Details

Catalina 30
1985 Groton Connecticut 30 Catalina 30
Length: 30'     Beam:  10.8'     Draft:  5.3'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Groton, Connecticut
Asking: $15,500
Sailboat Added 18-Feb-2025  More Details

C&C 41
1985 Westport Connecticut 41 C&C 41
Length: 41'     Beam:  12-11'     Draft:  7'-10'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Westport, Connecticut
Asking: $24,950
Sailboat Added 13-Feb-2025  More Details

Hobie Hobie Cat 16
 Stamford Connecticut 16 Hobie Hobie Cat 16
Length: 16'
Type: daysailer
Hull: fiberglass  catamaran
Engine: other inboard
Location: Stamford, Connecticut
Asking: $1,500
Sailboat Added 15-Jan-2025  More Details

Featured Sailboat:  Albin Vega
1973 Haddam Connecticut 27 Albin Vega
Length: 27'     Beam:  8'     Draft:  3'10'
Year: 1973
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Haddam, Connecticut
Asking: $3,500
Featured Sailboat Added 13-Oct-2025  More Details

ODay
Length: 17.8'     Beam:  6.2'     Draft:  8'
Year: 197
Type: daysailer
Hull: fiberglass  monohull
Location: Stonington, Connecticut
Asking: $550
Sailboat Added 16-Nov-2024  More Details

ODay 2
Length: 17'     Beam:  6.3'     Draft:  83'
Year: 1970
Type: daysailer
Hull: fiberglass  monohull
Location: Stonington, Connecticut
Asking: $550
Sailboat Added 16-Nov-2024  More Details


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