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

Brokerage Sailboats

Listings Updated 02/24/15

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
25 Hunter 25.5 1985 Whad'ya Need It For? Roomy 25.5 model with pop top. Newer items include: 2003/07 North sails, 2012 Harken roller furling, 2011 standing rigging, and 2011 Yamaha 8hp, 4 cycle electric start outboard. Clean! Used for daysailing in Lake Michigan by one owner since 1990. Stored over winters, mostly outside shrinkwrapped, at Crowley's Yacht Yard in Chicago. Well maintained annually, fresh bottom paint, oil changes, etc. 5,000
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'. 37,500
27 Catalina 1985 Felicitas Wheel, diesel, roller furling, new sails 2011, interior cushions and cockpit cushions excellent. 9,900
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
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. 24,000
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. 18,500
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). 9,000
29 Soverel Yawl 1965 Miller Shoal draft, keel centerboard. New Electric Motor in 2011: ElectricYacht 180ibl. New Harken traveler in 2011. Harken Lazy Jacks in 2009. Furlex roller furling in 2006. 2 self-tailing winches (2008). Stored indoors heated over winters 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. 49,900 UA
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 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
30 Catalina 30 Tall Rig 1987 Nirvana Well-kept boat, always fresh water sailed in Lake Michigan. Very attractive accommodations, including shower and electric refrigeration. Diesel engine, VC-17 bottom.
Marine Survey - June 2014
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; blue canvas dodger. 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. 28,500
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! 37,500
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. Newer sails. 31,000
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
30 Seidelmann 299 1979 Allez A well-maintained example of a 299. Used for daysailing in Chicago (Lake Michigan). Fantastic bright work, mechanicals in good repair, never any major damage. Yanmar engine is reliable with seasonal oil and filter changes.
Original Brochure
Maintenance Record
ATN Spin Tacker video
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
Marine Survey
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
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 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 Beneteau 343 2005 Shady Lady In-mast furling mainsail. One owner, always fresh water. Shady Lady's very conscientious and maintenance-focused owners used her for daysailing, long and short range cruising on Lake Michigan. All systems in working condition. Prepaid winter storage.
Marine Survey
34 C&C 34 1981 Far Niente Traditional racer/cruiser with Yanmar diesel engine. Very clean inside and out. 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 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 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. 34,000
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. 45,000
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. 50,000
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 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
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. 49,500
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, and a new stereo with blue-tooth and Bose speakers in cabin and cockpit. 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. The two head design, with a private head forward in the owner's cabin, is great for weekends aboard with two couples or children. 119,000
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

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