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

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.

1981 Hunter 22 Sailboat With Trailer

1981 Hunter 22 Sailboat With Trailer

$2,100

Granite City, Illinois

Year 1981

Make Hunter

Model -

Category Sailboats

Length 22.0

Posted Over 1 Month

This 1981 Hunter Quality Sailboat Is In Great Shape. Everything Works like it should. New Main and Jib Halyards. She Can be a Trailer Sailer, Weekend Getaway or Leave her in the Marina For That Nice Place On The Water. Sleeps 4 Comfortably, or just you and a guest. Comes With Trailer with All New Bunk Boards. This leaves your options open for what lake to sail on, or to leave it in the water or bring it home to save on Marina Fees. She is at time of Listing Moored at Alton Marina In IL, 62002. Till End Of October, or Sooner Trailered. Don't Miss Your Chance to Sail the Mississippi, or Perhaps do The Great Loop. We Have Many Loopers Stop At This Marina. Comes With 3 Sails, Original Hunter 22 Main Sail With Hunter Logo. and 2 Jib Sails 100% & 120% all Having their own sailbags. Not real sure on the %,, one looks original size,, and the other is Bigger. ALL In Great Condition. Nice Lock Down Rudder with Nice Woodwork on the Tiller. Classic Teak And Holly Sole, Cleans Up Real Pretty. 2' Draft means you can go almost anywhere with this boat, and I have. You can pull her right up on the beach, and then while sailing, drop the Keel, for really Stable Feel. Some have done the Great Loop In Lesser Boats. Trailer Is Known as a Magic Tilt Trailer, which has a Built In Extender Pole, which I haven't needed to use, but nice in case you need it. Brakes need some work, but I haven't found the need for them really,, is why I never gave them any attention. Really hate to sell,, it has been a lot of fun with the family, and friends, Don't have to sail,, you can put an outboard on her and just putter around,.and fish from the cockpit, which has a nice fold down Table. Clear Title To Boat And Trailer. I Have All Documentation for The Sailboat and Trailer. I believe I am The Second Owner,, Not Positive. Owners Manuals, Rigging Instructions, Wiring Diagrams,, and BTW,,being an electrician, I Neatened Up All Wiring. Wire Ties, No Spaghetti Mess. No Outboard Comes with the Boat. The One I Have On There is a Home Made 7hp lawn mower Motor attached to a lower unit,, Worked Great,, But it is Mine. One Off Original.. see youtube on how to do this,, cheap easy, reliable one pull outboard. DRY DRY DRY. No Leaks, Always Dry inside. Lots Of Storage Areas.

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!

1981 Hunter 22 Sailboat With Trailer

1981 Hunter 22 Sailboat With Trailer

$2,800

Granite City, Illinois

Year 1981

Make Hunter

Model -

Category Sailboats

Length 22.0

Posted Over 1 Month

This 1981 Hunter Quality Sailboat Is In Great Shape. Everything Works like it should. New Main and Jib Halyards. She Can be a Trailer Sailer, Weekend Getaway or Leave her in the Marina For That Nice Place On The Water. Sleeps 4 Comfortably, or just you and a guest. Comes With Trailer with All New Bunk Boards. This leaves your options open for what lake to sail on, or to leave it in the water or bring it home to save on Marina Fees. She is at time of Listing Moored at Alton Marina In IL, 62002. Till End Of October, or Sooner Trailered. Don't Miss Your Chance to Sail the Mississippi, or Perhaps do The Great Loop. We Have Many Loopers Stop At This Marina. Her Name Is Briar Patch. So.... Be sure to warn your guest when entering...... js. jk. Comes With 3 Sails, Original Hunter 22 Main Sail With Hunter Logo. and 2 Jib Sails 100% & 120% all Having their own sailbags. Not real sure on the %,, one looks original size,, and the other is Bigger. ALL In Great Condition. Nice Lock Down Rudder with Nice Woodwork on the Tiller. Classic Teak And Holly Sole, Cleans Up Real Pretty. 2' Draft means you can go almost anywhere with this boat, and I have. You can pull her right up on the beach, and then while sailing, drop the Keel, for really Stable Feel. Some have done the Great Loop In Lesser Boats. Trailer Is Known as a Magic Tilt Trailer, which has a Built In Extender Pole, which I haven't needed to use, but nice in case you need it. Brakes need some work, but I haven't found the need for them really,, is why I never gave them any attention. Really hate to sell,, it has been a lot of fun with the family, and friends, Don't have to sail,, you can put an outboard on her and just putter around,.and fish from the cockpit, which has a nice fold down Table. Clear Title To Boat And Trailer. I Have All Documentation for The Sailboat and Trailer. I believe I am The Second Owner,, Not Positive. Owners Manuals, Rigging Instructions, Wiring Diagrams,, and BTW,,being an electrician, I Neatened Up All Wiring. Wire Ties, No Spaghetti Mess. No Outboard Comes with the Boat. The One I Have On There is a Home Made 7hp lawn mower Motor attached to a lower unit,, Worked Great,, But it is Mine. One Off Original.. see youtube on how to do this,, cheap easy, reliable one pull outboard. DRY DRY DRY. No Leaks, Always Dry inside. Lots Of Storage Areas. Buy It Now Option= After Completion of Sale, Delivery within a 800 miles. Just contact me first so we can discuss. Email With Phone Number.

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!

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.

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

Chrysler Mutineer 15 ft Dinghy Day Sailer New Sails Main and Jib Trailer

Chrysler Mutineer 15 ft Dinghy Day Sailer New Sails Main and Jib Trailer

$1,500

Schaumburg, Illinois

Year 1975

Make -

Model Chrysler Mutineer 15

Category Sailboats

Length 15.0

Posted Over 1 Month

This is a used boat purchased in 2008. It has the usual dings and scratches with a boat this old. she is seaworthy and can be sailed as soon as purchased. Great boat to single hand or with up to 4 people. she has 2 brand new sails from Super Sail Makers and the old original main is still usable. The trailer recently made a trip to Cape Cod, the wheels are good and bearing were packed. Trailer will need paint and I am rerigging with new lights for new owner. She is located in Schaumburg Illinois and it is Local pickup as I have sold my truck. I have had awesome experiences with this boat and I am moving up to a 24 footer. So its time for ZOZO CIRCUS to find a new home and owner. the price is $1500 or best offer. I added a motor mount as well. Sale Price includes Boat, Trailer, 3 Sails 2 main and Furling Jib as well as new sheets/lines for main jib and boom. Tiller and Dagger/Center board as well. Boat has Wisconsin title. please email me for details [email protected]

2004 MacGregor M26 Sailboat 50h/p Outboard Engine Trailer Included CDI Furling

2004 MacGregor M26 Sailboat 50h/p Outboard Engine Trailer Included CDI Furling

$18,800

Deerfield, Illinois

Year 2004

Make MacGregor

Model 26M

Category Sailboats

Length 26.0

Posted Over 1 Month

Before you send an offer or click the buy it now, please call me at 847 736 8585 ! -----ANY OFFER WITHOUT A PRIOR PHONE CALL WILL BE DENIED----- ***2004 MacGregor 26M Sailboat with 50h/p Mercury Outboard Engine*** *MacGregor Trailer with New Tires Included - Take the Boat Anywhere - It Only needs 14" of Water to Float * ***CDI Roller Furler Installed with Jib Sail - Also New Genoa Sail Included - All Sales Are Excellent*** ***Leather Seat Cushions for the Boat are Without Rips or Tears in Excellent Shape*** ***It Has Navigation, Marine Radio, Gas BBQ, Fridge, Microwave, Porta potty, Solar Battery Charger, Bumpers, Life Vests, Flotation Devices, Signal Gun, A bunch of Ropes, Mast Raising System, Extra Set of New Boat Riggings Metal Lines, Extra Rudder, Bilge Pump and Registration Until 2017*** ***The Boat is Ready for the Water and Does Not Need Anything*** ***I Keep the Boat on the Trailer at My Local Marina for $50/Month - takes me 10 min to be in the water*** Watch the MacGregor Video here: WATCH THE MACGREGOR VIDEO HERE Don't Assume Anything - Call 847 736 8585 and I'll do a walk around the vehicle for you! Please contact me by phone or email before you submit an offer or click the BUY IT NOW option. I have to talk to a live person before accepting any offers! If you have any questions, please call me at (847) 736 8585 Usually my actions end with a phone call...