Sailboat Sales Co. - Brokerage Sailboats for sale in Chicago


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

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

Brokerage Sailboats

Listings Updated 07/18/19

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
22 Marshall Catboat 2002 Nepenthe Beautiful, one-owner, excellent condition, well-maintained, always-fresh-water, low-hour, gaff rig, centerboard, Marshall 22 catboat loaded with factory options and custom-built amenities. Indoor heated storage every winter. SOLD
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 Beneteau First 25 S 2013 Vagabundo One owner boat, very lightly used for weekend sailing since new in August 2014. Always fresh water sailed in the Chicago area. Regularly maintained by Crowley's Yacht Yard since new. Stored shrink-wrapped every winter. 49,900
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. 57,000
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
29 Tanzer 1987 Voila Diesel engine, roller furling. New mainsail in 2019. Genoa new in 1998. Aft cabin with double berth. 9,000
30 Catalina 30 TR wing keel 1992 Winsome Wing keel, shallow draft. Used for day sailing and light cruising on Lake Michigan. Autopilot. VC-17 bottom. Updates include newer spinnaker and satellite radio. 15,000
30 Hinterhoeller Nonsuch 30 Ultra 1986 Peace On Earth Fresh water sailed since 2006. New in 2008 Raymarine instruments. Autohelm Smartpilot 6002, and Garmin 2010c GPSmap w/ Lake Michigan chart. EPIRB. Lewmar folding wheel. Walker Bay 8' dinghy. SOLD
30 Sabre 30 MKIII 1988 Essence Beautifully kept and maintained Sabre 30. Always fresh water sailed. One owner since new. Always stored indoors heated over winters. Truly remarkable condition. 37,000
32 Sabre 1986 Bevo's Babe Always fresh water sailed. New Yanmar diesel engine in 2017. Raymarine ST60+ instruments. 5 sails. 33,000
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.
November 2018 marine survey
Note: Buyer has signed work order with Crowley's to address survey issues. SOLD
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 Beneteau 343 2008 Siren Always fresh water, one-owner, well-maintained boat, daysailed only, never cruised or raced. Raymarine instruments including autopilot. In-mast furling main, and roller furling genoa. Interior features 6' 2" headroom, great ventilation and light, and very comfortable 6" mattresses in forward and aft cabins. SOLD
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. 19,500
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.
Cruising World article about the Peterson 34 12,000
35 J Boats J/35 1984 Bretwalda Raced/Cruised on Great Lakes only. Includes Chartplotter, New sails in 2016. Steel cradle. SOLD
36 Beneteau First 36.7 2002 Findar One owner boat, always Lake Michigan sailed. Very well maintained. SOLD
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
37 Jeanneau Sun Odyssey 37 2005 Spirit in the Night 2 cabin version. Bow thruster. Original sails. Furling main and genoa. Electric anchor windlass. Autopilot not operational. Boat has been in a time share program since new. Always fresh water sailed in Chicago area. 75,000
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. 65,000
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. SOLD
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. SOLD

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
22	Marshall Catboat	2002	Nepenthe	Beautiful, one-owner, excellent condition, well-maintained, always-fresh-water, low-hour, gaff rig, centerboard, Marshall 22 catboat loaded with factory options and custom-built amenities. Indoor heated storage every winter.	SOLD
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	Beneteau First 25 S	2013	Vagabundo	One owner boat, very lightly used for weekend sailing since new in August 2014. Always fresh water sailed in the Chicago area. Regularly maintained by Crowley's Yacht Yard since new. Stored shrink-wrapped every winter.	49,900
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.	57,000
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
29	Tanzer	1987	Voila	Diesel engine, roller furling. New mainsail in 2019. Genoa new in 1998. Aft cabin with double berth.	9,000
30	Catalina 30 TR wing keel	1992	Winsome	Wing keel, shallow draft. Used for day sailing and light cruising on Lake Michigan. Autopilot. VC-17 bottom. Updates include newer spinnaker and satellite radio.	15,000
30	Hinterhoeller Nonsuch 30 Ultra	1986	Peace On Earth	Fresh water sailed since 2006. New in 2008 Raymarine instruments. Autohelm Smartpilot 6002, and Garmin 2010c GPSmap w/ Lake Michigan chart. EPIRB. Lewmar folding wheel. Walker Bay 8' dinghy.	SOLD
30	Sabre 30 MKIII	1988	Essence	Beautifully kept and maintained Sabre 30. Always fresh water sailed. One owner since new. Always stored indoors heated over winters. Truly remarkable condition.	37,000
32	Sabre	1986	Bevo's Babe	Always fresh water sailed. New Yanmar diesel engine in 2017. Raymarine ST60+ instruments. 5 sails.	33,000
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. November 2018 marine survey Note: Buyer has signed work order with Crowley's to address survey issues.	SOLD
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	Beneteau 343	2008	Siren	Always fresh water, one-owner, well-maintained boat, daysailed only, never cruised or raced. Raymarine instruments including autopilot. In-mast furling main, and roller furling genoa. Interior features 6' 2" headroom, great ventilation and light, and very comfortable 6" mattresses in forward and aft cabins.	SOLD
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.	19,500
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. Cruising World article about the Peterson 34	12,000
35	J Boats J/35	1984	Bretwalda	Raced/Cruised on Great Lakes only. Includes Chartplotter, New sails in 2016. Steel cradle.	SOLD
36	Beneteau First 36.7	2002	Findar	One owner boat, always Lake Michigan sailed. Very well maintained.	SOLD
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
37	Jeanneau Sun Odyssey 37	2005	Spirit in the Night	2 cabin version. Bow thruster. Original sails. Furling main and genoa. Electric anchor windlass. Autopilot not operational. Boat has been in a time share program since new. Always fresh water sailed in Chicago area.	75,000
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.	65,000
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.	SOLD
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.	SOLD

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