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

Brokerage Sailboats

Listings Updated 10/12/15

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
20 Alerion Express 20 1997 Ellie For pure sailing pleasure, what more do you need. Only 2 owners. Lake Michigan boat for the last 14 years, the first 4 years before that were on the ocean. Roller furling jib. Outboard motor. Cradle. SOLD
25 Cal 25 MKII w/ trailer 1982 Instead Large cockpit, beamy cabin. Sleeps two in V-berth, two in salon, and one in starboard quarter-berth. Inboard diesel, roller furling, trailer. 7,999
25 Catalina 25 1985 My Joy Beautiful clean white Catalina 25 is ready to sail. Tiller steering, Pop-Top companionway. 1998 Yamaha 9.9 electric start outboard motor, 2012 North Sails mainsail with sail cover, and 2012 North Sails furling genoa. Fixed keel with 4-ft draft. Always fresh water sailed. 4,900
27 Catalina 270 LE 1994 Francis B. Wing keel, shallow 3-1/2 foot draft. Used for pleasure sailing on Lake Michigan. Always fresh water. The main salon has an open layout that includes the forward sleeping area; private aft sleeping area is fully-wide. Perkins diesel engine, custom cockpit cushions, roller furling, dodger and sailcover. wheel steering with Autohelm Insturments and autopilot at helm, custom cockpit table, Apelco VHF. 19,500
27 Ericson 27 1977 Aquater Always fresh water sailed. Fin keel (3' 11" draft), wheel steering, roller furling genoa. Inboard Atomic 4 gas engine. Port and starboard settees with dining table center. Forward vee berth, enclosed marine head with holding tank, and quarterberth. Galley is aft to port. Teak bulkhead and trim. Headroom is 6' 1" 7,500
27 Island Packet 1989 Endeavor Always fresh water sailed, well maintained boat. New 2014 standing rigging, lifelines, & electronics. 37,500
29 Bayfield 29C Cutter 1983 Arr!! Trailer and dinghy. Three owners since new, sailed exclusively on Lakes Erie and Michigan. Summers at Jackson Harbor and winters at Crowley's Yacht Yard. Yanmar diesel engine maintained by CYY. This boat is clean and dry, the current owner has been very attentive to keeping the boat in very good condition. Wheel steering. SOLD
30 Catalina 30 Tall Rig 1981 Nittany Rigged and ready to go sailing. A good old boat, only 2 owners since new and always on Lake Michigan. Current owner since 1983 has kept this boat in nice condition. Blue fabric upholstery is in very good condition. Rare teak-and-holly cabin sole. Stern perch seats, Lewmar winches, roller furling genoa, autopilot, full instrumentation. All lines lead aft for single-handed sailing. Atomic 4 inboard engine and drive train in perfect running condition.
Recent marine survey available to serious buyers.
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. 23,500
30 Columbia Sport Sailor 2006 Heart Throb One-owner, always fresh-water sailed. Retractable keel. Trail-Rite twin-axle trailer. Inboard Yanmar diesel with Saildrive. Open transom. VC-17 bottom. PHRF rating of 78. Nexus NX2 Multi instrument package. New UK Tape Drive Gold Powerhead mainsail in 2012. Click thru to Full Specs for complete sail inventory.
Original Brochure & Builder's Comments
Original Invoice (not including sails)
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. 7,500
30 Pearson 30 1972 Doctor Chicago Only 3 owners. Always sailed in Chicago / Lake Michigan. Current owner has owned since 1980. A very well cared for with significant updates. With auto-pilot on the tiller, easily cruised single-handed. All interior cushions are in beautiful condition. Stored at Crowley's Yacht Yard; outdoors, mast up, shrink-wrapped.
Video: Tiller Pilot Demo
Video: Bird's-Eye-View
Read the reviews:
Sailing Magazine / Cruising Sailboat blog / BoatUS
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.
31 Hunter 31 2006 A Wink and a Smile Always Lake Michigan sailed, one-owner Hunter 31. Sailed out of Hammond Marina. Features include in-mast furling mainsail; furling genoa; Selden rigid boom vang; stainless steel arch with mainsheet traveler and cockpit speakers; Lewmar folding steering wheel; walk-through transom. 6' 4" headroom in main cabin. 59,900
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
32 J Boats J/32 1997 Whisper Great sailing boat. Flag Blue Awlgrip topsides (new in 2006.) Silky smooth VC-17 bottom. Always fresh water boat. Dodger, roller furling, autopilot. Great Lakes sailed; never raced. Winter storage has been indoor heated. 70,000
32 O'Day 32 Center Cockpit 1977 Peregrine Lake Michigan sailed boat. Only 3 owners since new. Stored on-land over winters. Regularly maintained. In-mast Roller Furling Mainsail. Dinghy davits. Full canvas cockpit enclosure. Sails recently repaired, New halyards in 2013. New fuel tank in 2013. New winter cover in 2013. 18,000
32 Sabre Tri-Cabin 1984 Vivace Fin keel, bright white beauty w/ tri-cabin interior. Always fresh water sailed. This is a great boat for a family and entertaining guests. The dinette and the cockpit easily fit 6 adults with room for food and beverages. Vivace take you anywhere you want to go in almost any weather. She tracks well and is a breeze to sail single handed. 35,000
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
33 Flying Tiger 10M 2006 Solitary Solitary has been professionally rigged and maintained. She is a proven winner in both one design and PHRF racing. The boat has completed the Mac race (with the previous owner) and can easily be Mac ready. The boat is very fast, stable, and remarkably easy to sail. Solitary is a freshwater boat – she has been sailed primarily in Chicago and Lake Lanier, GA. The boat is easy to trailer and ramp launch. 45,000
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. 62,000
34 C&C 34 1981 Far Niente Traditional racer/cruiser with Yanmar diesel engine. Reasonably clean. Sails are like new. 13,000
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! 19,000
34 Hunter 34 1986 Esprit Du Vent Fall 2014: topsides and transom professionally washed, buffed and waxed plus fresh anti-fouling bottom paint - keel sides and keel to hull joint excellent .... interior thoroughly cleaned; mast and rigging, sails and electrical and electronics professionally checked out. 18,000
35 Bristol 35 1967 Talisman Well maintained and updated Bristol 35. Dinette table converts to double berth, total of 5 sleeping spaces. ST4000+ autopilot, GPS, new LED interior lighting, new VHF, new bluetooth stereo, new 2500 watt inverter, new microwave, new antifouling bottom and barrier coat, new water heater. 14,000
35 C&C 35 MK III 1985 Mr. JJ Updated electronics, sails, winches, etc. The C&C 35 MK III truly offers exceptional cruising and racing performance. She has the speed to win on the race course and offers the comfort for extended cruising. The mechanical systems and running rigging are up to date and have always been very well maintained. 47,900
35 CAL 35 1984 Bliss A Lake Michigan boat with spacious accommodations. Universal disel engine. 19,000
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. 39,000
36 C&C 110 2006 Liquid Date II One owner boat. Carbon fiber mast and retracting bow sprit. Volvo diesel sail drive. Folding prop. 54" leather covered wheel. Raymarine GPS/Chartplotter. Autopilot. Interior is cherry wood and leather upholstery. 6' 4" headroom. Enclosed head with shower. Sleeps 6. Galley with 2-burner stove/oven, microwave, and refrigerated ice box. 149,000
36 Catalina 36 1985 Pura Vida Boat has been sailed on the Great Lakes for its entire life. Currently on its third owner, since 2001. Boat has never had major damage. Maintenance by Crowley's Yacht Yard upon their suggestions and review of vessel annually during haul out. Boat has been stored on its own cradle with shrink wrap at Crowley's each winter. Bottom in very good condition, having been fully repainted in 2001 and annual recoat of VC-17. Interior in good condition. Exterior teak refinished in August 2014. SOLD
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
36 Sabre 362 1994 Sven Christian Sven Christian is a one owner, always fresh water, standard keel, garage kept example of the highly successful Jim Taylor-designed Sabre 362. SOLD
37 Hunter Legend 1989 Kaleidoscope Well cared for boat sailed in Lake Michigan by current owners since 1993. Wing keel 4' 9" draft. Sleeps 6. 6' 4" headroom. New fabric cushions in 2013. New refrigerator/freezer in 2014. Autohelm 4000+ (new in 2014). Garmin Chartplotter (new in 2010). Mainsail with cover and Dutchman (new in 2010). Marine Head (new in 2014). Main halyard winch is electric. 48,000
38 Sydney 38 2000 Serenissima Price reduced for quick sale, but still excellent throughout, exclusively fresh water sailed/raced, great sail inventory.
article from Australian Yachting magazine
Sydney 38 photos
Sydney 38 overview
Sydney 38 specs
Sydney 38 layout
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
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

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