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

Brokerage Sailboats

Listings Updated 09/15/14

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
20 Com-Pac Horizon Cat 2005 Anna B Cape Cod shoal-draft cat rigged, easy handling, roomy weekend cruiser. Easy towing and launching from the included double-axle trailer. This boat has an inboard Yanmar diesel engine. SOLD
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. 4,000
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. 12,000
27 Hunter 1982 Lakeride Very good condition, ready to sail, only 2 owners. Autopilot, newer UK sails, furling genoa, wheel steering. SOLD
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
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). 10,000
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 1981 Bill's
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. Owner Very Motivated! 16,500
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 MKII Tall Rig 1989 Wild Thyme Always fresh water cruised boat. Only two owners. 1st owner stored the boat indoors every winter. 2nd owner bought the boat in the fall of 2004 and stored the boat outdoors under a custom winter canvas cover every year. Boat has been consistently well maintained in excellent condition. This boat is fun and easy to sail with the help of the Autohelm 4000 autopilot and Hood Seafurl roller furling. Sails are new in 2008. Central air conditioning was added in 1999. Steel storage cradle is included. Boat is now at Monroe Harbor in Chicago. Please call us today to schedule a showing.
Marine Survey
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. 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. 33,000
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
32 SeƱorita 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
33 Carroll Marine Frers 33 1988 Mystify Aways fresh water sailed. Many recent improvements. New Kiwi Grip non-skid deck.
Rig Survey Bottom Survey
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. 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
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. Very clean inside and out. Sails are like new. 13,000
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
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 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
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. Topsides waxed and buffed annually, shrink wrapped in winters. 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
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
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

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