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

Brokerage Sailboats

Listings Updated 04/16/14

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
27 Catalina 1985 Felicitas Wheel, diesel, roller furling, new sails 2011, interior cushions and cockpit cushions excellent. 12,000
28 Catalina 28 1990 Pommes Frites Wing keel. Overall maintenance is very good. Always fresh water sailed on Lake Michigan, daysailing and light cruising. Diesel engine. 2007 UK roller furling genoa, newer rudder, Dutchman, sailcover. SOLD
28 S2 8.5 Meter Sloop 1981 Orinoco Solid, stable, and fast, popular boat on the Great Lakes, also a nice size for cruising the man-made lakes along major inland river systems. Lazy jacks mainsail and new roller furling genoa. Tiller steering creates a roomy cockpit, the spacious and attractive interior is sure to please the family. Shore power with Adler Barbour refrigerator and freezer. Used for daysailing. 9,500 UA
28 Tartan 28 1984 Euphoria A rare opportunity to own a Sparkman & Stephens designed sailing yacht. Only 2 owners, always sailed in fresh water on Lake Michigan shoreline out of scenic and historic Wilmette Harbor. Boat has been donated to a charitable organization, the Yanmar diesel engine was serviced and winterized in November by Crowley's Yacht Yard, professional cleaning crew is scheduled to go aboard. Donor reports never any major damage. Overall condition is reported as average. Tiller steering. 2006 performance sails from North Sails Chicago: full batten mains'l and NorLam performance/furling 155% genoa w/ trim stripes, UV leech and foot. 16,000
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). 19,000
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. 25,000
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; new dodger in 2012. 29,000
30 Catalina 30 Tall Rig 1981 Bill's Michael-een Very well maintained with long list of upgrades. Only 3 owners and always in Lake Michigan. Wheel steering with boat leather cover and binnacle compass. Universal Atomic 4 engine. Sleeps 7. New cushions in 2005. Screens and curtains. Hot and cold pressure water. Garmin GPS. New VHF w/ remote mic. 155% roller furling genoa, new in 2008. New Jabsco marine head in 2011. Electronic ignition new in 2011. 18,500
30 Catalina 30 1983 Club Mel Too Always popular, this Catalina 30 has had only 2 owners and has been in Lake Michigan. All electronics are described as being in good working condition. Auto pilot. New cockpit cushions. The diesel engine was overhauled in 2012 by Crowleys Yacht Yard. Survey from 2012 is available. 19,800
30 Catalina 30 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. 33,000
30 Helmsman 30 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. 12,000
30 Hunter 30 1976 Quinn Mary Too This Hunter 30 has shoal draft keel, pedestal steering, and diesel engine. The interior offers generous use of teak, including swing down table. Large berths, enclosed head with stand-up shower, two large hatches, dockside power. Galley includes 2-burner stove, stainless steel sink, hot/cold pressure water, and lots of working space. Quinn Mary Too has always been in fresh water - Lake Michigan - with only 3 owners since new. Features a shiny new Interlux Fiberglass Bottomkote NT anti-fouling black bottom (Oct 2011). 6,950 UA
33 CAL 33 MKII 1988 My Doctor Exceptional boat. Owner moving. Never raced. Fast, comfortable and well-built fresh-water racer/cruiser. Sail area/displacement ratio of 18.08, respectable 7+ hull speed, good windward performance, deep fin keel, and spacious interior. Sleeps six, over 6-ft standing headroom in salon, nicely appointed interior, teak toe rails on deck, stout looking sailboat. Dependable Yanmar engine. 34,500
33 Hunter 336 1996 Impulse Huge oval-shaped cockpit makes this boat the perfect platform for entertaining large groups of friends and family on the water. Below-decks features windows everywhere and 4 deck hatches for ample light and ventilation. Air conditioning and heat. Wing keel allows access to shallower areas. Always a Lake Michigan boat, never in salt water. SOLD
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. 72,000
34 C&C 34 1981 Far Niente Traditional racer/cruiser with Yanmar diesel engine. New listing. Details and photos to follow. 19,000
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. 49,900
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. 40,000
35 Pearson Alberg 35 1962 September Song Has only had three owners (the current owner's father was owner #2). Hull number 7. Always sailed on Lake Michigan. Topsides and deck are painted with AWL-GRIP (~2011). New Sitka spruce boom. Universal diesel (~2002).
Marine Survey
36 Pearson 365 Ketch 1981 Marcia Ann II Only 1 owner and always in fresh water (Lakes Erie and Michigan). Very clean boat, well maintained, gorgeous and elegant interior with private berth forward, separate shower stall, u-shaped galley. Engine professionally maintained, topsides waxed and buffed annually, shrink wrapped in winters. 38,000
37 Hunter Legend 37 1990 Orion New listing. Details to follow.
Survey from December 2012
38 Morgan 382 1978 Serena Always fresh water sailed and always stored and maintained at Crowley's from day one, this Morgan 382 is a very solidly-built traditional-looking boat that can handle all weather conditions. Many recent upgrades, including Yanmar diesel engine in 2001. Survey from 2008 SOLD
38 Sydney 38 2000 Serenissima Price reduced for quick sale, but still excellent throughout, exclusively fresh water sailed/raced, great sail inventory. 111,000
38 Sydney 38 2000 Painkiller 4 One-owner boat, used exclusively in Lake Michigan. Wheel steering. 155,000
39 Beneteau Oceanis 393 2002 Baldr Heating, air conditioning, two cabins, two heads, in-mast furling mainsail. Built in South Carolina. Very large cockpit with teak drop-down table. 2 extra seats on the stern railing. Only one owner since new, member of Chicago Yacht Club, daysailing and light cruising in Lakes Michigan and Huron. Never any major damage. All maintenance by Crowley's Yacht Yard in Chicago. Winter storage has always been indoor heated with mast down. Includes custom steel cradle.
New Survey from December 2013
39 Dufour 39 CC 1999 SouthSide Magic Very well maintained center cockpit yacht used exclusively in Lake Michigan. Only 2 owners and always lightly used for daysailing only. Air conditioning, in-mast furling mainsail, large aft stateroom. Professionally maintained by Crowley's Yacht Yard, price includes cradle and custom winter cover. Fresh coat of VC-17 in 2013.
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. 44,750
40 Catalina 400 MKII 2003 Tomorrow's Sunshine One owner boat, always fresh water sailed, meticulously maintained and in excellent condition throughout. In-mast furling main and furling genoa. Electric anchor windlass. Fischer Panda diesel generator. Edson twin pedestal steering with Ritchie compasses and Raymarine Hybridtouch Multifunction displays at each wheel. Many recent upgrades including new UK performance mainsail and genoa in 2006; Tides Marine high-performance low-friction mainsail track and slide system in 2006; 2 new North spinnakers in 2008 & 2010; 2 new heads in 2010, (electric head is forward and manual head with separate shower is aft). All new Raymarine electronics in 2012. 183,000
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. 55,000
42 Pacer Yachts Pacer 42 CR 2006 Madrugada Great sailing vessel fully equipped for short-handed family cruising or competitive trans ocean racing. IRC rating is 1.146. Lake Michigan PHRF 2013 Certificate available by request. Polyester Composite Hull with Gelcoat Finish. Epoxy Deck with painted finish. Very well cared for. Stored indoors by current owner for the last two winters. Boat was in the BVI for the two years before that. Current owner is the third owner. 184,900
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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