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Your search returned 263 matches of 107754 sailboats posted to date

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Featured Sailboat:  Hunter 30
1978 Dry dock Chicago until 510 Monroe Harbor Chicago after Illinois 30 Hunter 30
Length: 30'     Beam:  8'     Draft:  5.25'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Dry dock Chicago until 510 Monroe Harbor Chicago after, Illinois
Asking: $14,000
Featured Sailboat Added 25-Mar-2025  More Details

Featured Sailboat:  Pearson Triton w/ Beta14 diesel aux eng
1965 Chicago Illinois 28.33 Pearson Triton w/ Beta14 diesel aux eng
Length: 28.33'     Beam:  8.25'     Draft:  3.92'
Year: 1965
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $12,000
Featured Sailboat Added 17-Mar-2025  More Details

CAL 2-27
1977 Waukegan Illinois 27 CAL 2-27
Length: 27'     Beam:  9'3'     Draft:  4'3'
Year: 1977
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Waukegan, Illinois
Asking: $7,700
Sailboat Added 08-Mar-2025  More Details



Blue Jacket BJ40
2014 Chicago Illinois 40 Blue Jacket BJ40
Length: 40'     Beam:  12'     Draft:  5'
Year: 2014
Type: other
Hull: fiberglass  
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $325,000
Sailboat Added 04-Feb-2025  More Details

ODay 27
1979 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 27 ODay 27
Length: 27'     Beam:  8'     Draft:  5'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $5,000
Sailboat Added 08-Jan-2025  More Details

ODay 27
1979 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 27 ODay 27
Length: 27'     Beam:  8'     Draft:  5'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $5,000
Sailboat Added 08-Jan-2025  More Details

Cal Yachts 27
1977 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 27 Cal Yachts 27
Length: 27'     Beam:  9.25'     Draft:  4.25'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $5,000
Sailboat Added 08-Jan-2025  More Details

Catalina 27 Tall Rig 27
1990 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 27 Catalina 27 Tall Rig 27
Length: 27'     Beam:  8.83'     Draft:  4'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $14,000
Sailboat Added 08-Jan-2025  More Details

Irwin Yachts 33
1977 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 30 Irwin Yachts 33
Length: 30'     Beam:  10.2'     Draft:  5'
Year: 1977
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $5,000
Sailboat Added 08-Jan-2025  More Details



Pearson Yachts 30
1972 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 30 Pearson Yachts 30
Length: 30'     Beam:  9.5'     Draft:  5'
Year: 1972
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $6,000
Sailboat Added 08-Jan-2025  More Details

Ranger 33
Ranger 33
Length: 33'     Beam:  9.58'     Draft:  5'
Year: 1971
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $12,000
Sailboat Added 08-Jan-2025  More Details

Endeavor 33
1985 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 33 Endeavor 33
Length: 33'     Beam:  11.50'     Draft:  4.50'
Year: 1985
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $17,500
Sailboat Added 27-Dec-2024  More Details

Catalina 30 Tall Rig
1979 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 30 Catalina 30 Tall Rig
Length: 30'     Beam:  10.83'     Draft:  5.25'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $14,000
Sailboat Added 16-Nov-2024  More Details

Catalina 36
1990 Chicago Illinois 36 Catalina 36
Length: 36'     Beam:  11'
Year: 1990
Type: cruiser
Hull: fiberglass  monohull
Engine: gas inboard
Location: Chicago, Illinois
Asking: $54,000
Sailboat Added 25-Oct-2024  More Details

Hunter Legend 37.5
1989 Chicago Illinois 37 Hunter Legend 37.5
Length: 37'     Beam:  18'3'
Year: 1989
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Chicago, Illinois
Asking: $45,000
Sailboat Added 25-Oct-2024  More Details

Wauquiez 38 MKI
1983 Chicago Illinois 38'3 Wauquiez 38 MKI
Length: 38'3'     Beam:  11'9'     Draft:  4'6'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $45,000
Sailboat Added 25-Oct-2024  More Details

Beneteau Oceanis 40
2012 Chicago Illinois 39.83 Beneteau Oceanis 40
Length: 39.83'     Beam:  12.83'     Draft:  5.08'
Year: 2012
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $175,000
Sailboat Added 17-Oct-2024  More Details

Jeanneau Sun Odyssey 37
2005 Chicago Illinois 37.33 Jeanneau Sun Odyssey 37
Length: 37.33'     Beam:  12.08'
Year: 2005
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $83,000
Sailboat Added 17-Oct-2024  More Details

Hunter Hunter 36
2005 Chicago Illinois 35.24 Hunter Hunter 36
Length: 35.24'     Beam:  12'     Draft:  4.92'
Year: 2005
Type: cruiser
Hull: fiberglass  monohull
Location: Chicago, Illinois
Asking: $83,000
Sailboat Added 17-Oct-2024  More Details



Jeanneau Sun Odyssey 40.3
2006 Chicago Illinois 40.03 Jeanneau Sun Odyssey 40.3
Length: 40.03'     Beam:  12.96'     Draft:  6.40'
Year: 2006
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $125,000
Sailboat Added 17-Oct-2024  More Details

Bennett Yachting VX One
2013 Chicago Illinois 19 Bennett Yachting VX One
Length: 19'     Beam:  7.17'     Draft:  4.33'
Year: 2013
Type: racer
Hull: fiberglass  monohull
Location: Chicago, Illinois
Asking: $22,000
Sailboat Added 05-Oct-2024  More Details

Elan Impression 344
2007 Chicago Illinois 34 Elan Impression 344
Length: 34'     Beam:  11'5'     Draft:  5'4'
Year: 2007
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: Chicago, Illinois
Asking: $78,000
Sailboat Added 23-Sep-2024  More Details

S2
1981  Illinois 26 S2
Length: 26'
Year: 1981
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Asking: $3,000
Sailboat Added 18-Sep-2024  More Details

Laguna Yachts Laguna 22
1986 Waukegan Illinois 22 Laguna Yachts Laguna 22
Length: 22'     Beam:  8'     Draft:  3'
Year: 1986
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Waukegan, Illinois
Asking: $2,900
Sailboat Added 02-Sep-2024  More Details

Hobie Cat Hobie 16
1984 Carlyle Illinois 16 Hobie Cat Hobie 16
Length: 16'
Year: 1984
Type: other
Hull: fiberglass  catamaran
Location: Carlyle, Illinois
Asking: $1,750
Sailboat Added 30-Aug-2024  More Details

Custom Ketch
2015 Waukegan Illinois 48 Custom Ketch
Length: 48'     Beam:  12.5'     Draft:  5.5'
Year: 2015
Type: cruiser
Hull: wood  monohull
Engine: 1 diesel inboard
Location: Waukegan, Illinois
Asking: $220,000
Sailboat Added 16-Aug-2024  More Details

Precision Boat Works 16.5
2000 Lake Holiday Illinois 16.5 Precision Boat Works 16.5
Length: 16.5'     Beam:  7'     Draft:  2.5'
Year: 2000
Type: cruiser
Hull: fiberglass  monohull
Location: Lake Holiday, Illinois
Asking: $4,800
Sailboat Added 07-Aug-2024  More Details

Hunter 280
Hunter 280
Length: 28'     Beam:  9'     Draft:  5'
Year: 1998
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Waukegan, Illinois
Asking: $22,000
Sailboat Added 22-Jul-2024  More Details

ODay ODay27
1978 Crowleys Yacht Yard Lakeside Chicago Illinois 27 ODay ODay27
Length: 27'     Beam:  9'     Draft:  4'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Crowleys Yacht Yard Lakeside Chicago, Illinois
Asking: $9,500
Sailboat Added 22-Jul-2024  More Details

Endeavour
1979 Winthrop Harbor Illinois 32 Endeavour
Length: 32'     Beam:  10'     Draft:  4'
Year: 1979
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Winthrop Harbor, Illinois
Asking: $12,000
Sailboat Added 01-Jul-2024  More Details

IRWIN COMPETITION
1976 Waukeegan  Larsen Marina Illinois 30 IRWIN COMPETITION
Length: 30'     Beam:  10.4'     Draft:  4.5'
Year: 1976
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Waukeegan Larsen Marina, Illinois
Asking: $8,750
Sailboat Added 26-Jun-2024  More Details



FLYING TIGER FT10M
Length: 32.66'     Beam:  9.15'     Draft:  7.62'
Year: 2005
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Chicago, Illinois
Sailboat Added 24-Jun-2024  More Details

Etchell
1981 Carlyle Illinois 30 Etchell
Length: 30'
Year: 1981
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 other outboard
Location: Carlyle, Illinois
Asking: $7,000
Sailboat Added 17-Jun-2024  More Details

Dyer Dink
1986 Chicago Illinois 10 Dyer Dink
Length: 10'
Year: 1986
Type: dinghy
Hull: fiberglass  monohull
Location: Chicago, Illinois
Asking: $1,800
Sailboat Added 11-Jun-2024  More Details

Hobie 16
Hobie 16
Length: 16.7'     Beam:  7.11'     Draft:  .8'
Year: 2020
Type: racer
Hull: fiberglass  catamaran
Location: Chicago, Illinois
Asking: $11,000
Sailboat Added 31-May-2024  More Details

Etchells 22
1995 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 30 Etchells 22
Length: 30'     Beam:  7'     Draft:  4.5'
Year: 1995
Type: racer
Hull: fiberglass  monohull
Engine: other outboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $12,000
Sailboat Added 29-May-2024  More Details

Hunter 34
1983 3434 E 95th St Illinois 34 Hunter 34
Length: 34'     Beam:  11'7'     Draft:  5'6'
Year: 1983
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: 3434 E 95th St, Illinois
Asking: $11,000
Sailboat Added 15-May-2024  More Details

Alden 309
1929 3434 E 95th St Illinois 43 Alden 309
Length: 43'     Beam:  12'5'     Draft:  7'0'
Year: 1929
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: 3434 E 95th St, Illinois
Asking: $175,000
Sailboat Added 15-May-2024  More Details

Catalina 30 TR
1986 3434 E 95th St Illinois 30 Catalina 30 TR
Length: 30'     Beam:  10'
Year: 1986
Type: cruiser
Hull: fiberglass  monohull
Engine: diesel inboard
Location: 3434 E 95th St, Illinois
Asking: $18,000
Sailboat Added 15-May-2024  More Details

Pearson 28
Pearson 28
Length: 28'5'     Beam:  9'3'     Draft:  4'6'
Year: 1980
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: 3434 E 95th St, Illinois
Asking: $11,000
Sailboat Added 15-May-2024  More Details

S2 9.2 c
 S2 9.2 c
Length: 30'     Beam:  10'4'     Draft:  4'11'
Year: 1979
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $9,600
Sailboat Added 29-Apr-2024  More Details

Catalina
2006 CARLYLE Illinois 25 Catalina
Length: 25'
Year: 2006
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: CARLYLE, Illinois
Asking: $19,400
Sailboat Added 23-Apr-2024  More Details

Catalina C-22
1982 Carlyle Illinois 22 Catalina C-22
Length: 22'
Year: 1982
Type: cruiser
Hull: fiberglass  monohull
Location: Carlyle, Illinois
Asking: $4,000
Sailboat Added 12-Apr-2024  More Details

Beneteau First 42
Beneteau First 42
Length: 42'     Beam:  13.6'
Year: 1985
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Sky Harbor Marina, Illinois
Asking: $49,000
Sailboat Added 06-Apr-2024  More Details

Islander 29
1968 chicago Illinois 29 Islander 29
Length: 29'     Beam:  8.83'     Draft:  3.67'
Year: 1968
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: chicago, Illinois
Asking: $17,000
Sailboat Added 27-Mar-2024  More Details

Jensen Cal 2-29
1978 chicago Illinois 29 Jensen Cal 2-29
Length: 29'     Beam:  9.25'     Draft:  4.50'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: chicago, Illinois
Asking: $7,000
Sailboat Added 27-Mar-2024  More Details

Hunter 310
1997 Carlyle Illinois 31 Hunter 310
Length: 31'
Year: 1997
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Carlyle, Illinois
Asking: $30,000
Sailboat Added 20-Mar-2024  More Details

Catalina MK1
Catalina MK1
Length: 29'9'     Beam:  10'8'     Draft:  5'3'
Year: 1975
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Waukegan, Illinois
Asking: $000
Sailboat Added 19-Mar-2024  More Details

Hobie Hobie 16
Length: 16'
Year: 1987
Type: other
Hull: fiberglass  catamaran
Engine: gas inboard
Location: Waukegan, Illinois
Asking: $3,500
Sailboat Added 25-Feb-2024  More Details

O'Day Outlaw
1968 Nautical Donations  Crowleys Yacht Yard  3434 E 95th St Chicago  Il 60617 Illinois 26 O'Day Outlaw
Length: 26'     Beam:  8'     Draft:  4.3'
Year: 1968
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: gas outboard
Location: Nautical Donations Crowleys Yacht Yard 3434 E 95th St Chicago Il 60617, Illinois
Asking: $5,000
Sailboat Added 24-Jan-2024  More Details

cuthbertson & cassion c & c 35 ll
1974 MONTROSE HARBOR WINTER STORAGE Illinois 35.50 cuthbertson & cassion c & c 35 ll
Length: 35.50'     Beam:  10.56'     Draft:  5.50'
Year: 1974
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: MONTROSE HARBOR WINTER STORAGE, Illinois
Asking: $24,000
Sailboat Added 08-Jan-2024  More Details

Pearson P26
1971 Chicago Illinois 26 Pearson P26
Length: 26'     Beam:  9'     Draft:  4'
Year: 1971
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Chicago, Illinois
Asking: $4,500
Sailboat Added 08-Jan-2024  More Details

Seaward 25 Seaward 25
1996 Nashville Illinois 25 Seaward 25 Seaward 25
Length: 25'     Beam:  8'     Draft:  2'
Year: 1996
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Nashville, Illinois
Asking: $24,000
Sailboat Added 02-Jan-2024  More Details

McLaughlin Optimist
2019 Lake Forest Illinois 8 McLaughlin Optimist
Length: 8'
Year: 2019
Type: dinghy
Hull: fiberglass  monohull
Location: Lake Forest, Illinois
Asking: $4,550
Sailboat Added 31-Oct-2023  More Details

Catalina Catalina 27
1978 Chicago Illinois 27 Catalina Catalina 27
Length: 27'     Beam:  9'     Draft:  4'
Year: 1978
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $7,200
Sailboat Added 03-Oct-2023  More Details

Ericson Ericson 39
1973 Chicago Illinois 39 Ericson Ericson 39
Length: 39'     Beam:  11.33'     Draft:  5.9'
Year: 1973
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 gas inboard
Location: Chicago, Illinois
Asking: $19,000
Sailboat Added 27-Sep-2023  More Details

Catalina 25
1986 Chicago Illinois 25 Catalina 25
Length: 25'     Beam:  8'     Draft:  4'
Year: 1986
Type: cruiser
Hull: fiberglass  monohull
Engine: 1 gas outboard
Location: Chicago, Illinois
Asking: $7,800
Sailboat Added 26-Sep-2023  More Details



Tuberas marine Gailee 15
1986 Excellent Illinois 15 Tuberas marine Gailee 15
Length: 15'     Beam:  6.7'     Draft:  3.7'
Year: 1986
Type: daysailer
Hull: fiberglass  monohull
Engine: gas outboard
Location: Excellent, Illinois
Asking: $2,500
Sailboat Added 25-Aug-2023  More Details

Beneteau First 40.7
Beneteau First 40.7
Length: 40'     Beam:  12.42'     Draft:  7.75'
Year: 1999
Type: racer/cruiser
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Chicago, Illinois
Asking: $84,900
Sailboat Added 01-Aug-2023  More Details

Catalina Tall rig
1978 Waukegan Illinois 30 Catalina Tall rig
Length: 30'     Beam:  10'     Draft:  5'
Year: 1978
Type: daysailer
Hull: fiberglass  monohull
Engine: 1 diesel inboard
Location: Waukegan, Illinois
Asking: $18,000
Sailboat Added 21-Jul-2023  More Details


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