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

Brokerage Sailboats

Listings Updated 07/24/17

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
21 Open Sailing - Pogo 2 2011 812 21' Mini 6.50m class racer. Has been used for daysailing only; never raced. Well equipped standing and running rigging. Fin keel with bulb & twin rudders. NKE autopilot. Six sails. Honda 5hp outboard motor. Custom dual-axle trailer. Well maintained, no damage ever, and upgraded electronics. Currently stored indoor heated at Crowley's Yacht Yard in Chicago. 59,000
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
27 Catalina 1986 Out & About Diesel, wheel, roller furling are a few of the features of this well-kept Catalina 27. Standing headroom, ready to go! Nice interior and cockpit cushions. 12,500
27 Hunter 27 2005 Trade Winds Nicely equipped 2-owner boat has sailed only in fresh water; Lake Carlyle and Lake Michigan. Boat has been well-maintained and is in very good condition. The 16 hp Yanmar diesel has only 186 original hours. The sails are currently being cleaned at UK Sail Makers in Chicago and will be available to see. UK has stored and maintained the sails over winters.
July 2013 marine survey 31,000
28 Catalina 28 Tall Rig 1992 View Finder Well maintained; always fresh water sailed; wing keel; battened mainsail; furling genoa; diesel; fresh bottom paint (fall 2016). SOLD
30 Beneteau First 305 1986 Missally One owner boat, always fresh water sailed in Lake Michigan. Newer sails. Furling genoa. Two spinnakers. Sleeps six. Custom winter cover. SOLD
30 JS Yachts Swarbrick JS9000 2003 Andzia Good condition. Very fast. Simple and easy to single-hand sail. Stored in heated building at Crowley's Yacht Yard in Chicago every winter since 2006. 21,000
31 Beneteau Oceanis 31 2015 Dawn Explosion This is a 1-year-old boat, Platinum Edition, fully equipped with factory upgrades. Only one owner, which should go without saying, and used exclusively for day sailing in Lake Michigan. Only 45 hours on the engine. All routine and required maintenance has been completed, winterization and engine service by Crowley's Yacht Yard. Its one winter was shrink wrapped. 119,900
31 Bruce Roberts 310 1989 Innovation Built by hand, entirely from scratch, by a man and his son in Mogadore Ohio. All steel construction -- hull, deck, reinforced transom. Hull-to-deck joint is welded. Interior cabinetry is well crafted and finely fit. Large V-berth area and extra long quarter berth. The boat is in remarkable condition. Fin keel, spade rudder with reinforced skeg. Two anchors on the bow, third anchor on the stern. Self-tailing winches. Diesel engine.
Marine survey from 2004 is available to qualified buyers.
Read about Innovation in Great Lakes Sailor 25,000
31 Capital Yachts Newport 31 1988 Sollevare Nice cruiser, sleeps 7. Autopilot. Wheel steering. Furling genoa. Lewmar winches: 3 regular & 2 self-tailing. 16,000
32 Pearson 323 1982 Breath Taking The Pearson 323, by renowned naval architect Bill Shaw, has over the years become an American classic. Only two owners since new. Always day sailed and cruised on Lake Michigan, no racing. Five sails including full spinnaker and gear, plus a 2007 furling genoa. Autohelm 3000. Harken roller furling. Wheel steering. 17,000
32 Hunter 320 2001 Irish Ayes Very lighly used. Professionally serviced and maintained by Crowley's Yacht Yard. Furling main and genoa; and autopilot make single-handed sailing a breeze. Always sailed in Lake Michigan in the Chicago area. Very clean and in fine condition. Newer Raymarine instruments. Smooth bottom painted spring 2016 with Pettit Hydrocoat. SOLD
33 Endeavour 33 1985 Mrs. Darling Beautiful teak interior. Autopilot and GPS. Yanmar diesel. A well maintained, well built sailing yacht maintained by a professional. Nice boat!
Marine Survey 21,000
34 Beneteau 343 2005 At Last In-mast furling mainsail. Always fresh water. Very conscientious and maintenance-focused owners used her for daysailing, long and short range cruising on Lake Michigan. All systems in working condition. Regularly stored shrink-wrapped in off season. Built in South Carolina, USA. July 2017: Deck and topsides washed, buffed and waxed. Interior cleaned and detailed. Cockpit/anchor lockers washed. Exterior teak surfaces cleaned and new Sikkens/Cetol applied.
Oct. 2014 Marine Survey 79,000
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! SOLD
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. 24,000
34 Sabre 34 1981 Maine Girl Beautiful woodwork on deck and interior. Sails beautifully. She is a fresh water boat and looks like it. New varnish 2015 fall deck and interior. 24,000
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 39,900
35 Hunter Legend 35.5 1990 Summer Key Always fresh water sailed on Lake Michigan. Very well maintained boat. Stored shrink-wrapped over winters. Excellent condition. 49,500
35 J Boats J/35 1984 Bretwalda Always fresh water raced/cruised on the Great Lakes. New sails in 2016. 18,000
36 Dufour 2007 Lily Features stylish modern lines and beautiful teak decks. Laid out for efficient sail handling or single-handed sailing. Shoal keel with 5' 7" draft. Removable bimini and dodger. 109,000
36 Mariner 1980 Sankaty Well known as ocean capable cruisers. Her hull features a fin keel and skeg-hung rudder for fast, balanced performance. The long waterline and ample beam provide a large cabin that is warmly finished with an abundance of teak.
Sankaty Blog by previous owner 20,000 UA
36 C&C 36 1979 Weatherly Clean and properly maintained racer/cruiser. Fully equipped for short handed sailing, or a full crew. Sails are all in good condition. Easy to sail and ready to go. 24,000
36 Sabre 1985 Wave Dancer Well maintained; and in excellent condition. New UK Mainsail in 2011. New Raymarine autopilot in 2013. GPS and chartplotter; Harken roller furling; Westerbeke diesel; 40" Destroyer wheel.
Marine Survey 58,000
37 Beneteau 2008 Chaika One owner boat, always fresh water sailed in Lake Michigan. Stored all winters under custom canvas cover. Central air conditioning; furling main and genoa; gps chartplotter, radar and autopilot. Excellent condition throughout. SOLD
37 Tartan 37 centerboard 1977 Zephyr Beautiful Tartan 37 with centerboard keel. Custom teak interior with genuine teak and holly sole. Five oversize self-tailing winches, Lofran anchor windlass, radar, B&G Pilot. Fresh water only. Professional annual maintenance. Stored winters indoors/heated at Crowley's Yacht Yard in Chicago. Summers at Belmont harbor in Chicago. Sparkman & Stephens design.
June 2017 Marine Survey 60,000
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 SOLD
40 Dufour 40 Performance 2005 Albatross Very well cared for Dufour 40 (40th Anniversary Edition), only one owner. Always sailed on Lake Michigan. Well maintained by a fastidious owner. All original manuals and equipment documentation available. Boat is used only 7-10 times a year, including several local races in the cruising division. The Dufour 40 is not only a good looking cruising boat, it’s also a fast boat that has won a few flags in Lake Michigan (cruising division). Winter custom made cover and cradle included.
• Dufour 40 - Original brochure
• Dufour 40 - Sail plan
• Dufour 40 - Polar diagram SOLD
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. 162,000
47 Carroll Marine Tripp 47 1992 Nautilus Fun and successful race boat. She has flagged in the Mackinaw race many times. Very competitive rating in both OOR and PHRF. Optimized with a custom keel and a masthead sail plan over the stock boat, featuring a 4 spreader carbon mast by Hall. Nautilus also has a user friendly interior well suited for cruising with family & friends, she makes a great dual purpose boat.
PHRF Certificate 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
21	Open Sailing - Pogo 2	2011	812	21' Mini 6.50m class racer. Has been used for daysailing only; never raced. Well equipped standing and running rigging. Fin keel with bulb & twin rudders. NKE autopilot. Six sails. Honda 5hp outboard motor. Custom dual-axle trailer. Well maintained, no damage ever, and upgraded electronics. Currently stored indoor heated at Crowley's Yacht Yard in Chicago.	59,000
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
27	Catalina	1986	Out & About	Diesel, wheel, roller furling are a few of the features of this well-kept Catalina 27. Standing headroom, ready to go! Nice interior and cockpit cushions.	12,500
27	Hunter 27	2005	Trade Winds	Nicely equipped 2-owner boat has sailed only in fresh water; Lake Carlyle and Lake Michigan. Boat has been well-maintained and is in very good condition. The 16 hp Yanmar diesel has only 186 original hours. The sails are currently being cleaned at UK Sail Makers in Chicago and will be available to see. UK has stored and maintained the sails over winters. July 2013 marine survey	31,000
28	Catalina 28 Tall Rig	1992	View Finder	Well maintained; always fresh water sailed; wing keel; battened mainsail; furling genoa; diesel; fresh bottom paint (fall 2016).	SOLD
30	Beneteau First 305	1986	Missally	One owner boat, always fresh water sailed in Lake Michigan. Newer sails. Furling genoa. Two spinnakers. Sleeps six. Custom winter cover.	SOLD
30	JS Yachts Swarbrick JS9000	2003	Andzia	Good condition. Very fast. Simple and easy to single-hand sail. Stored in heated building at Crowley's Yacht Yard in Chicago every winter since 2006.	21,000
31	Beneteau Oceanis 31	2015	Dawn Explosion	This is a 1-year-old boat, Platinum Edition, fully equipped with factory upgrades. Only one owner, which should go without saying, and used exclusively for day sailing in Lake Michigan. Only 45 hours on the engine. All routine and required maintenance has been completed, winterization and engine service by Crowley's Yacht Yard. Its one winter was shrink wrapped.	119,900
31	Bruce Roberts 310	1989	Innovation	Built by hand, entirely from scratch, by a man and his son in Mogadore Ohio. All steel construction -- hull, deck, reinforced transom. Hull-to-deck joint is welded. Interior cabinetry is well crafted and finely fit. Large V-berth area and extra long quarter berth. The boat is in remarkable condition. Fin keel, spade rudder with reinforced skeg. Two anchors on the bow, third anchor on the stern. Self-tailing winches. Diesel engine. Marine survey from 2004 is available to qualified buyers. Read about Innovation in Great Lakes Sailor	25,000
31	Capital Yachts Newport 31	1988	Sollevare	Nice cruiser, sleeps 7. Autopilot. Wheel steering. Furling genoa. Lewmar winches: 3 regular & 2 self-tailing.	16,000
32	Pearson 323	1982	Breath Taking	The Pearson 323, by renowned naval architect Bill Shaw, has over the years become an American classic. Only two owners since new. Always day sailed and cruised on Lake Michigan, no racing. Five sails including full spinnaker and gear, plus a 2007 furling genoa. Autohelm 3000. Harken roller furling. Wheel steering.	17,000
32	Hunter 320	2001	Irish Ayes	Very lighly used. Professionally serviced and maintained by Crowley's Yacht Yard. Furling main and genoa; and autopilot make single-handed sailing a breeze. Always sailed in Lake Michigan in the Chicago area. Very clean and in fine condition. Newer Raymarine instruments. Smooth bottom painted spring 2016 with Pettit Hydrocoat.	SOLD
33	Endeavour 33	1985	Mrs. Darling	Beautiful teak interior. Autopilot and GPS. Yanmar diesel. A well maintained, well built sailing yacht maintained by a professional. Nice boat! Marine Survey	21,000
34	Beneteau 343	2005	At Last	In-mast furling mainsail. Always fresh water. Very conscientious and maintenance-focused owners used her for daysailing, long and short range cruising on Lake Michigan. All systems in working condition. Regularly stored shrink-wrapped in off season. Built in South Carolina, USA. July 2017: Deck and topsides washed, buffed and waxed. Interior cleaned and detailed. Cockpit/anchor lockers washed. Exterior teak surfaces cleaned and new Sikkens/Cetol applied. Oct. 2014 Marine Survey	79,000
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!	SOLD
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.	24,000
34	Sabre 34	1981	Maine Girl	Beautiful woodwork on deck and interior. Sails beautifully. She is a fresh water boat and looks like it. New varnish 2015 fall deck and interior.	24,000
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	39,900
35	Hunter Legend 35.5	1990	Summer Key	Always fresh water sailed on Lake Michigan. Very well maintained boat. Stored shrink-wrapped over winters. Excellent condition.	49,500
35	J Boats J/35	1984	Bretwalda	Always fresh water raced/cruised on the Great Lakes. New sails in 2016.	18,000
36	Dufour	2007	Lily	Features stylish modern lines and beautiful teak decks. Laid out for efficient sail handling or single-handed sailing. Shoal keel with 5' 7" draft. Removable bimini and dodger.	109,000
36	Mariner	1980	Sankaty	Well known as ocean capable cruisers. Her hull features a fin keel and skeg-hung rudder for fast, balanced performance. The long waterline and ample beam provide a large cabin that is warmly finished with an abundance of teak. Sankaty Blog by previous owner	20,000 UA
36	C&C 36	1979	Weatherly	Clean and properly maintained racer/cruiser. Fully equipped for short handed sailing, or a full crew. Sails are all in good condition. Easy to sail and ready to go.	24,000
36	Sabre	1985	Wave Dancer	Well maintained; and in excellent condition. New UK Mainsail in 2011. New Raymarine autopilot in 2013. GPS and chartplotter; Harken roller furling; Westerbeke diesel; 40" Destroyer wheel. Marine Survey	58,000
37	Beneteau	2008	Chaika	One owner boat, always fresh water sailed in Lake Michigan. Stored all winters under custom canvas cover. Central air conditioning; furling main and genoa; gps chartplotter, radar and autopilot. Excellent condition throughout.	SOLD
37	Tartan 37 centerboard	1977	Zephyr	Beautiful Tartan 37 with centerboard keel. Custom teak interior with genuine teak and holly sole. Five oversize self-tailing winches, Lofran anchor windlass, radar, B&G Pilot. Fresh water only. Professional annual maintenance. Stored winters indoors/heated at Crowley's Yacht Yard in Chicago. Summers at Belmont harbor in Chicago. Sparkman & Stephens design. June 2017 Marine Survey	60,000
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	SOLD
40	Dufour 40 Performance	2005	Albatross	Very well cared for Dufour 40 (40th Anniversary Edition), only one owner. Always sailed on Lake Michigan. Well maintained by a fastidious owner. All original manuals and equipment documentation available. Boat is used only 7-10 times a year, including several local races in the cruising division. The Dufour 40 is not only a good looking cruising boat, it’s also a fast boat that has won a few flags in Lake Michigan (cruising division). Winter custom made cover and cradle included. • Dufour 40 - Original brochure • Dufour 40 - Sail plan • Dufour 40 - Polar diagram	SOLD
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.	162,000
47	Carroll Marine Tripp 47	1992	Nautilus	Fun and successful race boat. She has flagged in the Mackinaw race many times. Very competitive rating in both OOR and PHRF. Optimized with a custom keel and a masthead sail plan over the stock boat, featuring a 4 spreader carbon mast by Hall. Nautilus also has a user friendly interior well suited for cruising with family & friends, she makes a great dual purpose boat. PHRF Certificate	SOLD

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