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Sailboats for Sale in Chicago

(1 - 15 of 18)
  1. Fabulous 1979 classic racer/cruiser 27' fiberglass sailboat. Full headroom in main salon and forward cabin, roomy and comfortable, bathro...
    Carol S. · 1 week ago
  2. Winter Storage Paid!! 1985 Catalina 25' Tall Mast, Fixed fin Keel. Pop-Top with cover. Roller Furler. Always sailed in Lake Michigan. Thi...
    Marketplace User ·1 day ago on SpreadMyAd
  3. WILCOX-CRITTENDEN No. zero Anchor Windlass / Winch pat. May 25, 1915 in perfect working condition. Manufactured in Middletown, Connecticu...
    Marketplace User ·4 days ago on SpreadMyAd
  4. 1981 wheel-drive Schock 36 New York A high performance cruising yacht, the Schock 36 New York was designed by architect Bill Cook and w...
    POP Yachts ·1 week ago on BoatTrader.com
  5. … Beautiful well maintained Sailboat ready for a new owner. This is a Classic, long overhangs, Solid Rig, Solid hul...
  6. 15+ft. one design world class boat. Shows normal wear. Trailer needs paint. Comes complete ready to sail. Sobstad main, Jib, and spinnake...
    Marketplace User ·1 week ago on SpreadMyAd
  7. 1981 Sunfish Sailboat. Refurbished Centerboard and tiler/rudder. Original sails, will require replacement ($100) Includes new road traile...
    Marketplace User ·2 weeks ago on SpreadMyAd
  8. … Located in Indian Head Park, IL Type of Boat: Sail Boat Year: 1991 Make: Catalina Model: 36 MK I Length: 36 Hour...
    The Boat & RV Group ·2 weeks ago on BoatTrader.com
  9. O'Day 222 is an easy to sail and easy to trailer day/weekend sailor that sleeps 4. The hull is solid and fiberglass is in terrific condit...
    Marketplace User ·2 weeks ago on SpreadMyAd
  10. 1969 Cal Yachts. Well Designed great to sail Now a Classic. Combination of Cal Fast and Yacht Comforts. Accommodations for 6. Galley Encl...
    Marketplace User ·2 weeks ago on ChooseYourItem
  11. … Decks have been Professionally Rebuilt. Blue Heaven is a freshwater Pearson 39.2 sloop. She is a great club racer ...
    Weber Yachts ·2 weeks ago on BoatTrader.com
  12. … Resourceful, ingenious,& committed to time honoured traditions of excellence, the history of Cheoy Lee is as va...
    POP Yachts ·4 weeks ago on BoatTrader.com
  13. … Dimensions Year: 2010 LOA: 45 feet, Beam: 14 feet 4 in Draft: 5ft 6in (shoal draft) Displacement: 22932lbs,Bal...
  14. 1984 MacGregor Sailboats 25 SAILBOAT, 1984 MacGregor 25 is versatile, swing-keel boat that provides great performance for the price. A gr...
  15. … , Sails cleaned, checked and mended this month. Main sail, genoa and spinnaker "no pole," autopilot, hand held GPS, VHF r...

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