Sailboat Sales Co. - Brokerage Sailboats for sale in Chicago


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

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Brokerage Sailboats

Listings Updated 01/16/19

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 Fairing Design 1987 Passasje Gorgeous and unique hand-made wooden boat, custom built by Chip Stuben. Pleasure sailed exclusively on Lake Michigan, and consistently well maintained by single owner since new. Major refit from 2012 by Wayne Shibley including: new Yanmar diesel, keel, taller mast, new cockpit seating, new rigging for single-handling. Includes trailer. Always stored indoor-heated over winters. 75,000
23 Irwin 1973 Sundog One owner since new. Sleeps 4. 5' 2" main cabin headroom. Retractable centerboard has been fixed in the up position for 25 years, sails well. Movement of centerboard can be restored if desired. New rudder in 2015. New teak in 2011. New sails in 2011. New outboard motor in 2009. 5,000
25 W.D. Schock Harbor 25 2012 Sally Forth Mastervolt inboard electric with folding prop. Tiller steering with newer tiller pilot. Raymarine depth sounder, knotmeter, trip log mounted on cockpit bulkhead. Newer chart plotter. Doyle Leisure Furl in-boom furling mainsail. Hoyt furling self-tacking jib system. Lewmar winches. Jabsco marine head. Custom Pacific galvanized tandem-axle trailer. 74,000
26 Morris Frances 26 1996 If Full keel double-ender designed by C.W. Paine, built by Morris Yachts of Maine. Was personal boat of Tom Morris. Offshore equipped, multiple sets of ground tackle, mechanical and electrical self-steering, Jordan series Drogue, 6 new sails, new dodger, custom Triad trailer, and two dinghies. Sailed mostly in Rhode Island Sound until 2003 then in Chicago from 2004. Stored indoors over winters.
July 2018 marine survey 50,000
30 Catalina 30TR 1982 Avanti always Lake Michigan sailed. Universal diesel 5411. Interior cushions are Sunbrella fabric, new in 2015. Plastimo autopilot. Raymarine instruments. Wheel steering. VC-17 bottom paint applied annually. New fuel tank. Rudder rebuilt in 2012. SOLD
30 Fisher Pilothouse Ketch 1975 Ice Hot GRP motorsailer built by Fairway Marine, Northshore in Great Britain, This boat offers wheelhouse comfort along with excellent seaworthiness. Go anywhere vessel. Design by Gordon Wyatt and Freeman, grp hull, superstructure and deck, aluminum window frames, full bilged hull, skeg hung rudder, fuel tank 200 ltrs., fresh water tank: 50 ltrs (plastic), mechanical wheel-steering in pilothouse, tiller steering in cockpit.
Marine Survey SOLD
30 O'Day 302 1989 Allegro Bright clean and spacious interior, lots of light, good-looking teak and upholstery. Exterior clean, ready to launch. Wheel steering, Raymarine Autohelm 4000 autopilot, Yanmar diesel, and Furlex roller furling. New Doyle genoa. November 20, 2018: All electronics were demonstrated and found to be in normal operating condition. Price includes shrink-wrap, and winter storage through spring 2019, including spring launch. SOLD
32 Sabre 1986 Bevo's Babe Always fresh water sailed. New Yanmar diesel engine in 2017. Raymarine ST60+ instruments. 5 sails. 33,000
33 Beneteau 2005 September Song One owner boat, always fresh water sailed. Well maintained, clean boat. Autopilot, furling main and genoa. SOLD
33 Bristol 1969 Sea Horse Sloop rig. Newer sails. Simrad autohelm (new - not installed). Tiller steering. Storage cradle. Universal Atomic 4 engine. 15,000
33 Hunter 336 1996 Tradewind II Huge oval-shaped cockpit plus two perch seats on the stern railing make 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. Sleep 2 in the private forward cabin, 2 more in the aft cabin, plus the dining settee converts to another bed. Cook on the LP oven/stove, or on the portable gas grill at the transom. Air conditioning and heat. Shower. Innovative spreader arrangement eliminates the need for a backstay, creating easy access from the large swim platform. Mainsail, roller furling genoa, and 2 spinnakers. Wing keel with bulb allows access to shallower areas. Always a Lake Michigan boat, never in salt water. 39,000
33 Tartan T-10 1984 Druid Professionally maintained by Crowley's Yacht Yard. New Awlgrip topsides in 2014. VC-17 bottom. Sleeps 6. Teak & holly cabin sole; porta potti head; Datamarine instruments; Garmin GPS; Steel storage cradle; spinnaker gear; Lewmar winches. 9 sails included. Dutchman mainsail control system. 15,000
34 Catalina 34 MKII 1999 Bamii Only two owners since new. Lightly daysailed on the Chicago lakefront since new. Excellent condition. Regularly maintained by Crowley's Yacht Yard every spring and fall since new. 2016 Mast/Rigging Report available. 470 engine hrs. In-mast furling main. Furling genoa. New autopilot 2017; clean VC 17 anti-fouling bottom.
2015 Mast and Rigging Inspection Report
Original Brochure SOLD
34 Hunter 34 1984 Glory Days Two-owner Hunter 34, always Lake Michigan sailed in the Chicago area. Raytheon ST4000+ Autopilot. Harken roller furling. Light, spacious interior, large salon area with starboard side dinette and port settee with nav station. Galley is starboard aft with good storage areas, double stainless steel sink and gimballed 2-burner stove with oven. Large private double aft cabin, and private forward cabin with vee berth, forward starboard side head with shower and vanity sink opposite to port. 12,000
34 Hunter 34 1983 Dream Catcher Always fresh water sailed. Current owner has owned, and professionally maintained the boat at Crowley's Yacht Yard since 1997. 22,500
34 Peterson 34 1980 Odyssey always sailed off the Chicago lakefront. In 2007 her decks were stripped, prepped and painted, both non-skid and smooth, and topsides/transom as well - all in sprayed Awlgrip. 12,000
34 Sabre 34 MKII 1986 Polaris 2 owner boat, always sailed only in fresh water on Lake Michigan. Always stored over winters on land with custom winter cover and mast removed. 45,000
35 C&C 35 MK III 1985 Mr. JJ Updated electronics, sails, winches, etc. New VC-17 sprayed bottom June 2016. The C&C 35 MK III offers exceptional cruising and racing performance. She has the speed to win on the race course and the comfort for extended cruising. The mechanical systems, running rigging and bottom/keel/rudder are up to date and have always been very well maintained.
• Sailing Magazine
• Designer's Comments SOLD
35 Freedom 35 1995 Star Dancer Beautiful Awlgrip blue hull. Accommodations for 7. Very well maintained. Many upgrades including new Doyle Stack Pack in 2017. Draft is 6' 6". Yanmar 3GM 29hp diesel. Autopilot. Chartplotter. Radar. Accommodations for seven. Two private cabins. 6' 2" headroom. Teak trim interior. Newer lifelines. Electric winch for mainsail halyard. 67,000
35 Hunter 35.5 1992 Wind Song Beautifully maintained. Boat shows like new. Among the features are Corian counters, CNG stove with 2 tanks, Achilles inflatable dinghy with 4hp Evinrude rebuilt in 2004, Heart inverter power management with upgraded alternator, newer Raytheon Autohelm instruments with repeaters at the Nav station, mast ladder, bos'uns' chair, hot and cold cockpit shower, swim deck and swim ladder. 46,500
35 J Boats J/35 1984 Bretwalda Raced/Cruised on Great Lakes only. Includes Chartplotter, New sails in 2016. Steel cradle. 16,000
36 Beneteau First 36.7 2002 Findar One owner boat, always Lake Michigan sailed. Very well maintained. 63,000
36 Peterson 36-2 1985 Tamesis Same owner since 1999. Professionally maintained by Crowley's since 2008. Always fresh water sailed. Newer standing rigging, hydraulic backstay, solid vang, binnacle compass, water heater, pump and filter. Sails new in 2000; UK main and jib. Draft is 6' 6". Beam is 12' 4". Yanmar 30hp diesel. Keel stepped mast. Wheel steering. Boat is in heated building at Crowley's and shown by appointment. 50,000
37 Hunter Legend 37.5 1989 Kaleidoscope Well cared for boat sailed exclusively in Lake Michigan. Long list of upgrades in the last 2 years including A/C and Heat in all cabins, new electronics, new dodger and bimini, new spring mattress in the spacious aft cabin, and much more. 48,000
37 Irwin Competition 37 1973 Geronimo The Irwin Competition 37 was one of the most successful performance cruising designs of the early-mid 1970s, regularly placing in the top positions in buoy and distance races in ports throughout the East and Gulf coasts and Great Lakes. Her generous cockpit, walkway and foredecks spaces combined with ultra-large volume interior spaces created a boat that was enjoyed by racing crews and cruising families alike. Geronimo has been owned by four Chicago area sailors, all of whom were serious, maintenance focused yachtsmen. 12,000
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
43 Beneteau 423 2007 Gyp-Sea Very clean, very beautiful, very well kept. Only one owner since new, always sailed in Lake Michigan. Two-cabin layout. Factory equipment includes VC17 bottom, ST60002+ Linear Type 2 Autopilot, Raymarine E80 Multifunction Nav D, Raystar 125 LP WAAS, satellite receiver, hatch screens, upgraded cushion fabric, gennaker gear, upgraded winches, electric flush toilet, electrical inverter. 151,900
46 Beneteau 46 2011 Enlightened Built in USA. One owner. Always fresh water sailed in Lake Michigan. Lightly used. Approximately 100 hours of sailing since new. New VC-17 applied annually. Always stored indoor heated over winters. Yanmar 76HP diesel engine; Air Conditioning/Heat (28,000BTU); Bow Thruster; Bimini and Dodger; 2 Harken ST50 Electric Primary Winches; 1 Electric Halyard Winch; Electric Windlass; Raymarine Autopilot ST70 with ST40 Linear Drive Arm; Raymarine E120W GPS; Raymarine ST70 Wind/Speed/Depth; Leather Interior Cushions. 249,000

LOA	Type	Year	Name	Remarks	Price
20	Fairing Design	1987	Passasje	Gorgeous and unique hand-made wooden boat, custom built by Chip Stuben. Pleasure sailed exclusively on Lake Michigan, and consistently well maintained by single owner since new. Major refit from 2012 by Wayne Shibley including: new Yanmar diesel, keel, taller mast, new cockpit seating, new rigging for single-handling. Includes trailer. Always stored indoor-heated over winters.	75,000
23	Irwin	1973	Sundog	One owner since new. Sleeps 4. 5' 2" main cabin headroom. Retractable centerboard has been fixed in the up position for 25 years, sails well. Movement of centerboard can be restored if desired. New rudder in 2015. New teak in 2011. New sails in 2011. New outboard motor in 2009.	5,000
25	W.D. Schock Harbor 25	2012	Sally Forth	Mastervolt inboard electric with folding prop. Tiller steering with newer tiller pilot. Raymarine depth sounder, knotmeter, trip log mounted on cockpit bulkhead. Newer chart plotter. Doyle Leisure Furl in-boom furling mainsail. Hoyt furling self-tacking jib system. Lewmar winches. Jabsco marine head. Custom Pacific galvanized tandem-axle trailer.	74,000
26	Morris Frances 26	1996	If	Full keel double-ender designed by C.W. Paine, built by Morris Yachts of Maine. Was personal boat of Tom Morris. Offshore equipped, multiple sets of ground tackle, mechanical and electrical self-steering, Jordan series Drogue, 6 new sails, new dodger, custom Triad trailer, and two dinghies. Sailed mostly in Rhode Island Sound until 2003 then in Chicago from 2004. Stored indoors over winters. July 2018 marine survey	50,000
30	Catalina 30TR	1982	Avanti	always Lake Michigan sailed. Universal diesel 5411. Interior cushions are Sunbrella fabric, new in 2015. Plastimo autopilot. Raymarine instruments. Wheel steering. VC-17 bottom paint applied annually. New fuel tank. Rudder rebuilt in 2012.	SOLD
30	Fisher Pilothouse Ketch	1975	Ice Hot	GRP motorsailer built by Fairway Marine, Northshore in Great Britain, This boat offers wheelhouse comfort along with excellent seaworthiness. Go anywhere vessel. Design by Gordon Wyatt and Freeman, grp hull, superstructure and deck, aluminum window frames, full bilged hull, skeg hung rudder, fuel tank 200 ltrs., fresh water tank: 50 ltrs (plastic), mechanical wheel-steering in pilothouse, tiller steering in cockpit. Marine Survey	SOLD
30	O'Day 302	1989	Allegro	Bright clean and spacious interior, lots of light, good-looking teak and upholstery. Exterior clean, ready to launch. Wheel steering, Raymarine Autohelm 4000 autopilot, Yanmar diesel, and Furlex roller furling. New Doyle genoa. November 20, 2018: All electronics were demonstrated and found to be in normal operating condition. Price includes shrink-wrap, and winter storage through spring 2019, including spring launch.	SOLD
32	Sabre	1986	Bevo's Babe	Always fresh water sailed. New Yanmar diesel engine in 2017. Raymarine ST60+ instruments. 5 sails.	33,000
33	Beneteau	2005	September Song	One owner boat, always fresh water sailed. Well maintained, clean boat. Autopilot, furling main and genoa.	SOLD
33	Bristol	1969	Sea Horse	Sloop rig. Newer sails. Simrad autohelm (new - not installed). Tiller steering. Storage cradle. Universal Atomic 4 engine.	15,000
33	Hunter 336	1996	Tradewind II	Huge oval-shaped cockpit plus two perch seats on the stern railing make 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. Sleep 2 in the private forward cabin, 2 more in the aft cabin, plus the dining settee converts to another bed. Cook on the LP oven/stove, or on the portable gas grill at the transom. Air conditioning and heat. Shower. Innovative spreader arrangement eliminates the need for a backstay, creating easy access from the large swim platform. Mainsail, roller furling genoa, and 2 spinnakers. Wing keel with bulb allows access to shallower areas. Always a Lake Michigan boat, never in salt water.	39,000
33	Tartan T-10	1984	Druid	Professionally maintained by Crowley's Yacht Yard. New Awlgrip topsides in 2014. VC-17 bottom. Sleeps 6. Teak & holly cabin sole; porta potti head; Datamarine instruments; Garmin GPS; Steel storage cradle; spinnaker gear; Lewmar winches. 9 sails included. Dutchman mainsail control system.	15,000
34	Catalina 34 MKII	1999	Bamii	Only two owners since new. Lightly daysailed on the Chicago lakefront since new. Excellent condition. Regularly maintained by Crowley's Yacht Yard every spring and fall since new. 2016 Mast/Rigging Report available. 470 engine hrs. In-mast furling main. Furling genoa. New autopilot 2017; clean VC 17 anti-fouling bottom. 2015 Mast and Rigging Inspection Report Original Brochure	SOLD
34	Hunter 34	1984	Glory Days	Two-owner Hunter 34, always Lake Michigan sailed in the Chicago area. Raytheon ST4000+ Autopilot. Harken roller furling. Light, spacious interior, large salon area with starboard side dinette and port settee with nav station. Galley is starboard aft with good storage areas, double stainless steel sink and gimballed 2-burner stove with oven. Large private double aft cabin, and private forward cabin with vee berth, forward starboard side head with shower and vanity sink opposite to port.	12,000
34	Hunter 34	1983	Dream Catcher	Always fresh water sailed. Current owner has owned, and professionally maintained the boat at Crowley's Yacht Yard since 1997.	22,500
34	Peterson 34	1980	Odyssey	always sailed off the Chicago lakefront. In 2007 her decks were stripped, prepped and painted, both non-skid and smooth, and topsides/transom as well - all in sprayed Awlgrip.	12,000
34	Sabre 34 MKII	1986	Polaris	2 owner boat, always sailed only in fresh water on Lake Michigan. Always stored over winters on land with custom winter cover and mast removed.	45,000
35	C&C 35 MK III	1985	Mr. JJ	Updated electronics, sails, winches, etc. New VC-17 sprayed bottom June 2016. The C&C 35 MK III offers exceptional cruising and racing performance. She has the speed to win on the race course and the comfort for extended cruising. The mechanical systems, running rigging and bottom/keel/rudder are up to date and have always been very well maintained. • Sailing Magazine • Designer's Comments	SOLD
35	Freedom 35	1995	Star Dancer	Beautiful Awlgrip blue hull. Accommodations for 7. Very well maintained. Many upgrades including new Doyle Stack Pack in 2017. Draft is 6' 6". Yanmar 3GM 29hp diesel. Autopilot. Chartplotter. Radar. Accommodations for seven. Two private cabins. 6' 2" headroom. Teak trim interior. Newer lifelines. Electric winch for mainsail halyard.	67,000
35	Hunter 35.5	1992	Wind Song	Beautifully maintained. Boat shows like new. Among the features are Corian counters, CNG stove with 2 tanks, Achilles inflatable dinghy with 4hp Evinrude rebuilt in 2004, Heart inverter power management with upgraded alternator, newer Raytheon Autohelm instruments with repeaters at the Nav station, mast ladder, bos'uns' chair, hot and cold cockpit shower, swim deck and swim ladder.	46,500
35	J Boats J/35	1984	Bretwalda	Raced/Cruised on Great Lakes only. Includes Chartplotter, New sails in 2016. Steel cradle.	16,000
36	Beneteau First 36.7	2002	Findar	One owner boat, always Lake Michigan sailed. Very well maintained.	63,000
36	Peterson 36-2	1985	Tamesis	Same owner since 1999. Professionally maintained by Crowley's since 2008. Always fresh water sailed. Newer standing rigging, hydraulic backstay, solid vang, binnacle compass, water heater, pump and filter. Sails new in 2000; UK main and jib. Draft is 6' 6". Beam is 12' 4". Yanmar 30hp diesel. Keel stepped mast. Wheel steering. Boat is in heated building at Crowley's and shown by appointment.	50,000
37	Hunter Legend 37.5	1989	Kaleidoscope	Well cared for boat sailed exclusively in Lake Michigan. Long list of upgrades in the last 2 years including A/C and Heat in all cabins, new electronics, new dodger and bimini, new spring mattress in the spacious aft cabin, and much more.	48,000
37	Irwin Competition 37	1973	Geronimo	The Irwin Competition 37 was one of the most successful performance cruising designs of the early-mid 1970s, regularly placing in the top positions in buoy and distance races in ports throughout the East and Gulf coasts and Great Lakes. Her generous cockpit, walkway and foredecks spaces combined with ultra-large volume interior spaces created a boat that was enjoyed by racing crews and cruising families alike. Geronimo has been owned by four Chicago area sailors, all of whom were serious, maintenance focused yachtsmen.	12,000
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
43	Beneteau 423	2007	Gyp-Sea	Very clean, very beautiful, very well kept. Only one owner since new, always sailed in Lake Michigan. Two-cabin layout. Factory equipment includes VC17 bottom, ST60002+ Linear Type 2 Autopilot, Raymarine E80 Multifunction Nav D, Raystar 125 LP WAAS, satellite receiver, hatch screens, upgraded cushion fabric, gennaker gear, upgraded winches, electric flush toilet, electrical inverter.	151,900
46	Beneteau 46	2011	Enlightened	Built in USA. One owner. Always fresh water sailed in Lake Michigan. Lightly used. Approximately 100 hours of sailing since new. New VC-17 applied annually. Always stored indoor heated over winters. Yanmar 76HP diesel engine; Air Conditioning/Heat (28,000BTU); Bow Thruster; Bimini and Dodger; 2 Harken ST50 Electric Primary Winches; 1 Electric Halyard Winch; Electric Windlass; Raymarine Autopilot ST70 with ST40 Linear Drive Arm; Raymarine E120W GPS; Raymarine ST70 Wind/Speed/Depth; Leather Interior Cushions.	249,000

HOME BROKERAGE SAILBOATS BROKERAGE POWERBOATS OUR STORY FOR BUYERS FOR SELLERS F.A.Q. LINKS CROWLEY'S