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



Brokerage Sailboats

Listings Updated 09/23/16

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
24 J Boats J/24 1985 Cats Paws Dry boat, clean, no soft spots. Sails in good condition. Outboard motor, dinghy, highway trailer. Must sell now! 4,999
29 Hunter 290 2000 M&Ms Very well cared for Hunter 290. Always daysailed on Lake Michigan. Standard 5' 4" fin keel offers excellent sailing performance. Completely new custom VC-17 sprayed bottom summer 2016; Yanmar diesel, wheel steering, autopilot, roller furling, 6' 2" interior headroom, cockpit dodger. Interior teak and bottom are in excellent condition. SOLD
30 Catalina 30 Tall Rig 1985 Tummler A lovely Catalina 30 TR with clean decks (no soft spots), smooth topsides and waterline and excellent bottom; no significant aging shortcomings; mainsail like new, excellent upgraded electronics, mainsheet traveler upgraded from standard and … rarely seen on boats in this price range: inboard adjustable genoa car/track system – allows you to optimise the sheet lead angle as you furl the roller furling headsail. Custom after-market velour cushions. 16,000
30 Catalina 30 Tall Rig 1987 Lydia In-boom furling mainsail. Always fresh water sailed Tall Rig with Universal diesel engine. Only two owners since new. New sails in 2009. Autohelm autopilot, wheel steering, instruments and compass on binnacle. WinchRite motorised winch handle. CNG oven with 2-burner stove. New marine head. Custom canvas cover. SOLD
30 Ericson 30 Plus 1985 All In All Popular Bruce King design. Fresh water boat in sail-away condition. Nice electronics including autopilot. 4-ft shoal draft. Smooth VC-17 bottom, Deck and topsides look excellent. Very clean boat. 21,000
30 Irwin 30 1977 Freebird Excellent choice for the casual day-sailor on a budget, this is a good old boat that has been faithfully maintained. Roomy cockpit, wide walkways, and ample interior volume. Always in Lake Michigan, never in salt water. 7,000
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. 133,900
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
35,000
32 Beneteau Oceanis 321 1995 Latitudes In-mast roller furling mainsail, roller furling genoa. The Beneteau Oceanis 321 features cherry interior finish and spacious accommodations including aft cabin. Only 2 owners since new, it's a Lake Michigan boat, great for daysailing and cruising, easy to handle. Shallow draft just over 4 feet. The boat has never suffered major damage and has been excellently maintained.
Original factory line drawings
Original factory spec sheet
SOLD
32 Pearson 323 1982 Breath Taking The Pearson 323, by renowned naval architect Bill Shaw, has over the years become an American classic. Only two owners since new. Always day sailed and cruised on Lake Michigan, no racing. Five sails including full spinnaker and gear, plus a 2007 furling genoa. Autohelm 3000. Harken roller furling. Wheel steering. 26,000
33 Endeavour 33 1985 Skidmarks Beautiful teak interior. Autopilot and GPS. Yanmar diesel. A well maintained, well built sailing yacht maintained by a professional. Nice boat!
Marine Survey
21,000
33 SOCA Sailboats LS 10 2002 Sail La Vie Created by Sparkman and Stephens, the original concept of the T-Ten was to create a fun offshore boat with great sailing characteristics and weekend capabilities. What emerged was the first true offshore one design boat. The boat was an immediate success. More than 380 of these boats were delivered and most are still actively sailed and raced across the country. The New LS10 is the modern fruition of this highly successful design with an updated deck that incorporates a full cabinhouse designed to provide more headroom. A fully enclosed head, convenient galley and optional fold-away table enhance the comfortable space below for entertaining or cruising.
Marine Survey - 2016
62,000
34 Catalina 34 MKII 1999 Bamii One owner boat. Lightly daysailed on the Chicago lakefront since new. Excellent condition. Regularly maintained by Crowley's Yacht Yard every spring and fall since new. In-mast furling main. Furling genoa.
Mast and Rigging Inspection Report
Catalina 34 MKII Original Brochure
64,000
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! 16,000
35 C&C 35 MK III 1984 Slapshot New instruments and sails. Exclusively sailed in fresh water by her two owners since new. Always at Monroe Harbor in downtown Chicago; always wintered at Crowley's Yacht Yard in Chicago.
Sailing Magazine
Designer's Comments
36,000
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
39,900
35 Catalina 350 2004 Weekend Retreat Fresh water boat, heat, air-conditioning, dehumidifier, auto pilot, gps chartplotter, built-in coffee maker, two anchors- one with full chain rode, electric windlass, bimini and dodger, full cockpit cushions, cockpit vhs, flat screen tv, low hours, one owner. SOLD
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. 52,000
36 K. Aage Nielsen Gumdrop Yawl Centerboard 1961 Magic Double-planked hull, mahogany over white cedar on white oak frames. Built by Paul E. Luke in East Boothbay, Maine. MAGIC is one of six sisters built to the Gumdrop design. She has been upgraded over the years as required and well cared for by very knowledgeable owners. Marine survey from 2010 is available. 32,000
36 Cape Dory 1982 Windslove One owner boat. Always Lake Michigan sailed, never in salt water. Perkins diesel engine, low hours. The sails, the cushions, and the dodger are stored off-site in a climate-controlled situation. 29,000
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 Always Lake Michigan sailed; 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
60,000
39 Dufour 39 CC 1999 Sara Very well maintained center cockpit yacht used exclusively in Lake Michigan, except for the last 2 years on Florida's Gulf Coast. Only 3 owners and always lightly used for daysailing only. Air conditioning, heating, in-mast furling mainsail, large aft stateroom. Clean Boat a 9.5 out of 10. 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
29,900
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





All Rights Reserved, ©1996 - 2013 Sailboat Sales Co.