Sailboat Sales Co - 3434 E. 95th St - Chicago Illinois 60617 - Phone 773.221.8880

Brokerage Sailboats

Listings Updated 04/25/17

Sailboat Sales Co. at Crowley's Yacht Yard in Chicago has the largest selection of used sailboats for sale in Chicago. Find out how we can help you buy a boat or sell a boat. For information on any of these boats for sale, or possibly others not listed, call us or use our Web Contact Form.

Click on any column header to sort the table, ascending or descending.
Click on boat name to view complete specs with equipment list and photos.
= Marine Survey and/or Mechanical Systems Evaluation Report available.
UA = Under Agreement

Your time is valuable. Please call ahead for an appointment, to help ensure your ability to board and see these boats.

LOA Type Year Name Remarks Price
21 Open Sailing - Pogo 2 2011 812 21' Mini 6.50m class racer. Has been used for daysailing only; never raced. Well equipped standing and running rigging. Fin keel with bulb & twin rudders. NKE autopilot. Six sails. Honda 5hp outboard motor. Custom dual-axle trailer. Well maintained, no damage ever, and upgraded electronics. Currently stored indoor heated at Crowley's Yacht Yard in Chicago. 65,000
23 Irwin 1973 Sundog One owner since new. Sleeps 4. 5' 2" main cabin headroom. Retractable centerboard has been fixed in the up position for 25 years, sails well. Movement of centerboard can be restored if desired. New rudder in 2015. New teak in 2011. New sails in 2011. New outboard motor in 2009. 5,000
28 Catalina 28 Tall Rig 1992 View Finder Well maintained; always fresh water sailed; wing keel; battened mainsail; furling genoa; diesel; fresh bottom paint (fall 2016). SOLD
30 Beneteau First 305 1986 Missally One owner boat, always fresh water sailed in Lake Michigan. Newer sails. Furling genoa. Two spinnakers. Sleeps six. Custom winter cover. SOLD
30 JS Yachts Swarbrick JS9000 2003 Andzia Good condition. Very fast. Simple and easy to single-hand sail. Stored in heated building at Crowley's Yacht Yard in Chicago every winter since 2006. 25,000
31 Beneteau Oceanis 31 2015 Dawn Explosion This is a 1-year-old boat, Platinum Edition, fully equipped with factory upgrades. Only one owner, which should go without saying, and used exclusively for day sailing in Lake Michigan. Only 45 hours on the engine. All routine and required maintenance has been completed, winterization and engine service by Crowley's Yacht Yard. Its one winter was shrink wrapped. 123,000
31 Bruce Roberts 310 1989 Innovation Built by hand, entirely from scratch, by a man and his son in Mogadore Ohio. All steel construction -- hull, deck, reinforced transom. Hull-to-deck joint is welded. Interior cabinetry is well crafted and finely fit. Large V-berth area and extra long quarter berth. The boat is in remarkable condition. Fin keel, spade rudder with reinforced skeg. Two anchors on the bow, third anchor on the stern. Self-tailing winches. Diesel engine.
Marine survey from 2004 is available to qualified buyers.
Read about Innovation in Great Lakes Sailor
31 Capital Yachts Newport 31 1988 Sollevare Nice cruiser, sleeps 7. Autopilot. Wheel steering. Furling genoa. Lewmar winches: 3 regular & 2 self-tailing. 21,000
32 Hunter 320 2001 Irish Ayes Very lighly used. Professionally serviced and maintained by Crowley's Yacht Yard. Furling main and genoa; and autopilot make single-handed sailing a breeze. Always sailed in Lake Michigan in the Chicago area. Very clean and in fine condition. Newer Raymarine instruments. Smooth bottom painted spring 2016 with Pettit Hydrocoat. 49,500
33 Endeavour 33 1985 Mrs. Darling Beautiful teak interior. Autopilot and GPS. Yanmar diesel. A well maintained, well built sailing yacht maintained by a professional. Nice boat!
Marine Survey
34 Beneteau 343 2005 At Last In-mast furling mainsail. Always fresh water. Very conscientious and maintenance-focused owners used her for daysailing, long and short range cruising on Lake Michigan. All systems in working condition. Regularly stored shrink-wrapped in off season. Built in South Carolina, USA. 79,000
34 Hunter 34 1984 Ten Year Itch Fast and fun to sail, with plenty of room in cabin. Always fresh water sailed. Numerous recent updates (see ad for details). Interior main cabin cushions are excellent. Working electronics, engine maintained by nationally renowned yard at end of each season, plus annual winterising of engine and sanitation system. Good opportunity for person wanting to maximise interior volume for the dollar! 12,000
35 C&C 35 MK III 1985 Mr. JJ Updated electronics, sails, winches, etc. New VC-17 sprayed bottom June 2016. The C&C 35 MK III offers exceptional cruising and racing performance. She has the speed to win on the race course and the comfort for extended cruising. The mechanical systems, running rigging and bottom/keel/rudder are up to date and have always been very well maintained.
Sailing Magazine
Designer's Comments
35 Hunter Legend 35.5 1990 Summer Key Always fresh water sailed on Lake Michigan. Very well maintained boat. Stored shrink-wrapped over winters. Excellent condition. 49,500
35 J Boats J/35 1984 Bretwalda Always fresh water raced/cruised on the Great Lakes. New sails in 2016. 33,000
36 Dufour 2007 Lily Features stylish modern lines and beautiful teak decks. Laid out for efficient sail handling or single-handed sailing. Shoal keel with 5' 7" draft. Removable bimini and dodger. 109,000
36 Sabre 1985 Wave Dancer Well maintained; and in excellent condition. New UK Mainsail in 2011. New Raymarine autopilot in 2013. GPS and chartplotter; Harken roller furling; Westerbeke diesel; 40" Destroyer wheel.
Marine Survey
37 Beneteau 2008 Chaika One owner boat, always fresh water sailed in Lake Michigan. Stored all winters under custom canvas cover. Central air conditioning; furling main and genoa; gps chartplotter, radar and autopilot. Excellent condition throughout. SOLD
40 C&C 40 1980 Incentive Sought-after racer/cruiser, very spacious teak interior, long berths, Yanmar diesel. Stretch-out room in every direction, all berths are at least 6' 6" long. Large galley. Light and airy with 3 opening deck hatches.
Marine Survey
C&C 40 - Still Turning Heads
40 Dufour 40 Performance 2005 Albatross Very well cared for Dufour 40 (40th Anniversary Edition), only one owner. Always sailed on Lake Michigan. Well maintained by a fastidious owner. All original manuals and equipment documentation available. Boat is used only 7-10 times a year, including several local races in the cruising division. The Dufour 40 is not only a good looking cruising boat, it’s also a fast boat that has won a few flags in Lake Michigan (cruising division). Winter custom made cover and cradle included.
Dufour 40 - Original brochure
Dufour 40 - Sail plan
Dufour 40 - Polar diagram
42 Beneteau 42 CC Clipper 2003 Tiger Lily Air conditioning. In-mast furling mainsail. Bow thruster. Beautiful center cockpit boat with large aft cabin with private head and shower compartment (additional head compartment forward). Large galley area. Large aft deck with drop-down swim platform. 185,000
42 Palmer Johnson Peterson 2-ton 1977 Sleeping Bear Always fresh water sailed, custom Peterson design that has been modified to provide comfortable cruising accommodations along with short handed sailing capability. Safety, convenience and performance in a well maintained, economical and pleasing vessel. New engine in 2007. 75,000
43 Beneteau 423 2007 Gyp-Sea Very clean, very beautiful, very well kept. Only one owner since new, always sailed in Lake Michigan. Two-cabin layout. Factory equipment includes VC17 bottom, ST60002+ Linear Type 2 Autopilot, Raymarine E80 Multifunction Nav D, Raystar 125 LP WAAS, satellite receiver, hatch screens, upgraded cushion fabric, gennaker gear, upgraded winches, electric flush toilet, electrical inverter. 173,000
47 Carroll Marine Tripp 47 1992 Nautilus Fun and successful race boat. She has flagged in the Mackinaw race many times. Very competitive rating in both OOR and PHRF. Optimized with a custom keel and a masthead sail plan over the stock boat, featuring a 4 spreader carbon mast by Hall. Nautilus also has a user friendly interior well suited for cruising with family & friends, she makes a great dual purpose boat.
PHRF Certificate
29,000 UA

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