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



Brokerage Sailboats

Listings Updated 05/22/15

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.

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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
25 Catalina 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
25 Jarvis Newman Friendship Sloop Pemaquid 1972 Narwhal Fresh brightwork on all spars, lazarette covers, hatch, hatchboards, running light boards, dorades, blocks. Boat has been lightly cruised and day-sailed in Lake Michigan off Milwaukee and Chicago. Never any damage. Excellent overall maintenance; minimum two coats Epiphanes on all brightwork annually. Low hours on diesel engine; winterized and oil changed annually; new impeller annually. LOA with bowsprit is 36'. SOLD
27 Catalina 1985 Felicitas Wheel, diesel, roller furling, new sails 2011, interior cushions and cockpit cushions excellent. 9,900
27 Catalina 270 LE 1995 Jambo A nice boat, used for daysailing in Chicago's Lake Michigan. Never seen salt water. Features auto-pilot. Wheel steering, roller furling genoa, asymmetrical spinnaker. Recent improvements. This one is a must-see. SOLD
27 Ericson 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" 8,500
27 O'Day 1978 Endurance Nice boat. Was dismasted in May 2012. Mast and shrouds were replaced and installed by Crowley's Yacht Yard in the summer of 2012. Many other recent upgrades include newer head sail with roller furler, mainsail with Dutchman, VHF, GPS, fuel tank and injector.
Marine Survey
6,000
28 Hunter 280 1998 Carpe Diem Very well kept 1998 Hunter 280 in Chicago. Shoal draft, wing keel; autopilot; GPS; Dutchman sail flaking system; solid vang; furling genoa; full bimini; AM/FM/CD w/ 4 speakers & more. Stored outdoors, mast up. SOLD
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. 17,500
29 C&C 29 1977 Avatar New Raymarine instruments in 2004; North mainsail in 2001; and North Genoa in 2003. VC-17 bottom (new in 2009). SOLD
30 Cape Dory 1985 Sojourner Beautifully cared for boat in excellent condition. New Doyle mainsail, Tides Marine sail track and Doyle Stack Pack in 2014. Newer electronics. Comfortable and inviting warm interior with well-cared for wood work. SOLD
30 Canadian Sailcraft CS 30 1985 Blueline Great opportunity to own this always fresh water sailed CS 30 from Canadian Sailcraft. One owner boat, always Lake Michigan sailed. Owner is retiring from boating. Excellent overall condition. Interior teak oiled annually. VC-17 bottom. Volvo diesel engine. 19,500
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.
Engine Inspection - June 2014
23,500
30 Catalina 30 Tall Rig 1989 Rita Marie Catalina 30 tall rig equipped for comfortable cruising; well maintained. Wheel steering; diesel engine; autopilot; roller furling genoa new in 2012. 25,000
30 Catalina 30 TR MkII 1992 Winsome Wing keel, shallow draft. Used for day sailing and light cruising on Lake Michigan. Very well maintained boat. Auto pilot. Smooth VC-17 bottom, gleaming topsides, varnished teak trim on deck. Many updates including new spinnaker, satellite radio. 24,500
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. Also, UK Tape Drive Jibs (2); UK airx 700 asymmetric spinnaker reacher; UK airx Matrix fractional asymmetric; and UK airx 600 Matrix PHRF asymmetric. 55,000
30 Hunter 29.5 1996 C'est Si Bon Excellent condition, very clean, only one owner since new. Never raced, daysailing in Lake Michigan, never ever in salt water. Montrose Harbor in the summers, shrink-wrapped at Crowley's in the winters. This one is a must see, must buy, must go sailing! SOLD
30 Hunter 30 1990 Wind Spirit II Only 1 owner since new, always sailed in southern Lake Michigan. Well cared for and it shows, washed and waxed annually and regular oil changes. Smooth VC-17 bottom. Wing keel. Yanmar diesel engine. Wheel steering. SOLD
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
9,600
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. 65,000
32 Señorita Helmsman 32 1978 Catharina A gentleman's or gentlewoman's day sailer, from well before the current rage -- i.e. as much fun as an Alerion 28 at a fraction of the price. Catharina has had only 1 owner its whole life, used strictly for day sailing in Chicago.
Original Brochure
Additional Brochure
Sail Plan
Sales Sheet
Schematics
Marine Survey
9,000
33 Carroll Marine Frers 33 1988 Mystify Always fresh water sailed... the Frers 33 does it all, she's a fast cruiser/racer cruiser; pretty interior, many recent improvements incl 2013 Kiwi Grip non-skid decks.
Rig Survey Bottom Survey
SOLD
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
25,000
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. 19,000
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 Hunter Legend 35 1987 Mischief Air conditioning. Walk-through transom. Same owner since 1996, used for daysailing in Chicago, very nice condition. Deep keel boat, updated sail inventory, Yanmar diesel engine. SOLD
35 Pearson 1973 Delos II The Pearson 35 keel-centerboard design was enormously success, enjoying a twelve year production run beginning in 1972. Delos II is a one-owner boat always moored in Monroe St. Harbor, Chicago; her decks and topsides were custom Awlgripped. Bottom/rudder in perfect condition. Teak toerails, grabrails and companionway trim in perfect condition, gloss varnished; new Yanmar diesel in 1997, only 1,200 hrs. This is the ultimate affordable gentleman's (or woman's) classic yacht daysailer/coastal cruiser. Interior in overall excellent condition. Newer Raytheon autopilot, varnished wheel, Harken roller furling system. Furling genoa. Doyle Stak-Pak main. SOLD
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. 40,000
36 Ericson Cruising 36C 1976 Equis Engine rebuilt 2013. New Borg Warner transmission in 2003. Fresh water cruised boat. Teak deck, mahogany interior. Professionally maintained. Well equipped for cruising. 46,000
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. 89,000
38 Endeavour 38CC 1990 Pamela Gorgeous Endeavour 38 Center Cockpit sailboat. Very low hours on the Yanmar 44hp diesel. Air conditioning. Flag Blue topsides, smooth performance bottom. Newer Fischer Panda 30 amp Generator. This boat is now at Crowley's Yacht Yard in Chicago. Stored indoors heated most winters.
original brouchure
color brouchure
65,000
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
99,000
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
34,900
40 Hunter 1987 Windshear Shoal keel, 5' draft,sloop rig, sailed out of Belmont harbor in Chicago since 2002. Aft owner's cabin with large double island bed, two private compartments. Teak and holly cabin sole throughout. Teak bulkheads, drawers, cabinetry and trim; forward private cabin with vee berth. Opening ports throughout including five in the master cabin. Nav station. L-shaped galley with refrigeration. 45,000
40 Hunter 1988 Robbery Lake Michigan boat. Excellent accommodations include owner's aft stateroom with two entrances, island bed, and private head with shower. Additional head with shower in the private forward cabin. Teak and holly cabin sole throughout. Teak bulkheads, drawers, cabinetry and trim. Opening ports throughout, plus plenty of deck hatches. Nav station. L-shaped galley with refrigeration. Survey from March 2012 47,000
40 Jeanneau Sun Odyssey 40 DS 2000 Balance Extremely clean, only 609 engine hours, always a fresh water boat, new mainsail installed in July 2014. The 40DS has tremendous room in the cockpit for guests and can accommodate 8 – 10 people comfortably … very different than other 40 foot designs. The starboard side helm also allows the skipper to adjust main and jib from one position without requiring your guests to move out of the way. SOLD
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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