Sailboats for sale in Illinois

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1959 Tsuboi Admiralty Boats Custom Built Ketch

1959 Tsuboi Admiralty Boats Custom Built Ketch

$39,900

Waukegan, Illinois

Year 1959

Make Tsuboi

Model Admiralty Boats Custom Built Ketch

Category Sailboats

Length 42'

Posted Over 1 Month

1959 Tsuboi Admiralty Boats Custom Built Ketch Chari Vari is 42' without boomkin and bowsprit and 52' with bowsprit and boomkin

1956 Sparkman and Stephens Mystic

1956 Sparkman and Stephens Mystic

$89,000

Dolton, Illinois

Year 1956

Make Sparkman And Stephens

Model Mystic

Category Sailboats

Length 40'

Posted Over 1 Month

1956 Sparkman and Stephens Mystic Built by Paul Molich in Denmark, MYSTIC was originally owned by Harold Oldak and sailed on Long Island Sound. Her current owner has kept her in Chicago for 40 years and updated her systems. The diesel engine dates from the 90's and her sails from early 2000's. The solid dodger in the front of the cockpit is original and something current builders could learn from.  The owner reports some wood work to be done in the transom but other than that she is  in sound shape. He has taken very good care of her for many years and thinks it is time to turn her over the helm to a new wooden boat enthusiast who will enjoy her as much as he has.  Survey available per request from 2008

1983 Islander 28 BAHAMA

1983 Islander 28 BAHAMA

$15,900

Winthrop Harbor, Illinois

Year 1983

Make Islander

Model 28 BAHAMA

Category Sailboats

Length 28'

Posted Over 1 Month

1983 Islander 28 BAHAMA, This boat shows great care and will make the new owner proud to own this classic. Trades Considered

1964 Pearson Vanguard

1964 Pearson Vanguard

$13,900

Dolton, Illinois

Year 1964

Make Pearson

Model Vanguard

Category Sailboats

Length 32'

Posted Over 1 Month

1964 Pearson Vanguard Beautiful well maintained Sailboat ready for a new owner. This is a Classic, long overhangs, Solid Rig, Solid hull - Basically a very sturdy boat with an incredible hull.  $10,000 in new decking installed 2011.

1979 C & C 25

1979 C & C 25

$5,000

Chicago, Illinois

Year 1979

Make C & C

Model 25

Category Sailboats

Length 25'

Posted Over 1 Month

1979 C & C 25 This classic C & C is ready to sail and a great value.

1981 Catalina 25

1981 Catalina 25

$5,000

Chicago, Illinois

Year 1981

Make Catalina

Model 25

Category Sailboats

Length 25'

Posted Over 1 Month

1981 Catalina 25 This well kept Catalina is a great starter boat, perfect for cruising the great lakes or smaller inland lakes.

1974 Morgan 28

1974 Morgan 28

$9,000

Chicago, Illinois

Year 1974

Make Morgan

Model 28

Category Sailboats

Length 28'

Posted Over 1 Month

1974 Morgan 28 If you are looking for a clean pre enjoyed Morgan Sail Boat well look no further because you have found it. Do not let the year fool you this boat has been well taken care of and is ready for it's new owner. Loaded up with with all the options! Very clean boat with a motivated seller. Please call Earl Wenzel (312)315-6474 or Kyle Sahs (630)639-7623 to schedule a viewing of this boat. *Remember that boat you are thinking about today someone else said the same thing yesterday, and they are ready today!

1989 Catalina 30 Tall Rig

1989 Catalina 30 Tall Rig

$26,000

Chicago, Illinois

Year 1989

Make Catalina

Model 30 Tall Rig

Category Sailboats

Length 30'

Posted Over 1 Month

1989 Catalina 30 Tall Rig  If you are looking for a clean pre enjoyed Catalina Sail Boat well look no further because you have found it. Do not let the year fool you this boat has been well taken care of and is ready for it's new owner. Loaded up with with all the options! Including but not limited to: TWO Sets of Sails that around 5 years old with new Sail Covers, Auto Helm, Fridge, alcohol stove, wall to wall carpet that goes well with all of the custom wood work that has been done to this boat! New Lines, new eisenglass for the dodger with sun canopy, microwave, 150 Jeanneau Jib, Fowl weather gear, life jackets, new window screens with a custom cabin doorway screen. Full parts and maintenance records, an available 2011 Boat survey. New prop in 2012 and custom exterior cushions to match the boat. Please contact our professional Sales Consultants to set up your viewing or with any other questions you may have. Please Call Earl Wenzel (312)315-6474 or Kyle Sahs (630)639-7623 to schedule a viewing of this boat. *Remember that boat you are thinking about today someone else said the same thing yesterday, and they are ready today!

1998 Catalina 320

1998 Catalina 320

$64,900

Winthrop Harbor, Illinois

Year 1998

Make Catalina

Model 320

Category Sailboats

Length 32'

Posted Over 1 Month

1998 Catalina 320, September Song is ready to sail today. This 320 has enough room for the whole family but can be easily handled by just the captain. Come see it today and hear the sounds of the water this September. Trades Considered

1991 Hunter 35.5 Legend

1991 Hunter 35.5 Legend

$44,999

Winthrop Harbor, Illinois

Year 1991

Make Hunter

Model 35.5 Legend

Category Sailboats

Length 35'

Posted Over 1 Month

1991 Hunter 35.5 LEGEND, This sailboat is water ready. Boasting the two stateroom layout with teak throughout the cabin, new Bimini dodger, new water heater, and prop (2014), also a winter storage cover is included. Recent service on the Yanmar Diesel engine, brand new TV and a new refrigerator along with a new microwave that has a pizza stove. Price just reduced, owner wants the boat sold. There is really too much to list. Please call if you are remotely interested. Trades considered.

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2023 Puffin Boat Puffin 860 Row

2023 Puffin Boat Puffin 860 Row

Hot Springs Village, AR

$3,800

1999 OSB John Boat

1999 OSB John Boat

Citrus Springs, FL

$10,000