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Sailboats for Sale in Chicago

(1 - 15 of 27)
  1. Pop Top allows for extra cabin room and ventilation Draft: 4’ 6”; Beam: 9’1”; Length: 25’ 7”; Displacement: 3,700 9.9 HP Mercury Outboard...
    Alison R. · 4 days ago
  2. ATN Spinnaker Sleeve 36' fits asymmetrical and symmetrical spinnakers with luff measurements from approx 37' - 48'. Also know as a spinna...
    Marketplace User ·1 day ago on SpreadMyAd
  3. … Boat is located in Michigan City,Indiana.Please contact the owner @ 219-510-XXXX...The sailboat is in super condition, f...
    BoatsFSBO.com ·1 day ago on BoatingBay
  4. 6' Forespar Reaching Strut. Pre-owned on sailboat mast to push spinnaker guy away from boat to give a better angle on the guy line to the...
    Marketplace User ·1 day ago on SpreadMyAd
  5. 1991 Catalina 42, over $10,000 in upgardes, new Harken headsail roller furler, new epoxy bottom with Trinidad SR anti-fouling paint. New ...
    Marketplace User ·2 days ago on SpreadMyAd
  6. A beautiful and well maintained Sailboat. Same owner for 30yrs. Atomic four engine tuned up 2016. New paint in 2007. Harken Roller furler...
    Marketplace User ·5 days ago on SpreadMyAd
  7. 1994 Hunter 240. Great compact cruiser that has a retractable keel and can be trailered easily (trailer comes with the boat) main sail an...
    Marketplace User ·6 days ago on SpreadMyAd
  8. … - Stock number076614 - A truly magnificent Vessel! The C&C 39 is one of the prettiest fiberglass boats ever buil...
    POP Yachts ·1 week ago on BoatingBay
  9. Sailboat Starwind 19 1982 and trailer Shoreline 1982, its ballast boat and has extra swing light centerboard, small cabin can sleep two o...
    Marketplace User ·1 week ago on SpreadMyAd
  10. Sail Star/Bristol 24 - $2200 24.6ft Heavy displacement cruiser with six feet of headroom below. Sleeps four comfortably. All winter stora...
    Marketplace User ·1 week ago on SpreadMyAd
  11. For sale by owner: 2002 Vanguard 15 Sailboat, Hull#1198, in very attractive condition. Includes 2 sets of Vanguard sails, custom travel t...
    Marketplace User ·2 weeks ago on SpreadMyAd
  12. Hobie sixteen catamaran sailboat. Yes, this is the timeless classic, why buy new when you can get a pre-owned 1 this cheap. Includes trai...
    Marketplace User ·2 weeks ago on SpreadMyAd
  13. … For Sale by Haggle Me - Hobart, Indiana
    VehicleSurf.com ·3 weeks ago on VehicleSurf
  14. Ready to cruise. Super Rig (high mast). Standing headroom. Heavy duty rigging, Lloyds Hull Certificate, sleeps 4, one owner, replaced hea...
    Sherwin D. · 1 week ago
  15. … This meticulously maintained Catalina 30 tall rig is as turn key ready as they come. With fresh VC-17 bottom paint in ...
    Chicago Yacht Works ·Over 4 weeks ago on BoatTrader.com

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