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 09/15/17

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. 47,000
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 Sabre 1978 Island Sunset Lake Michigan cruised, well maintained classic Sabre 28. Sturdy boat, diesel engine, roller furling, wheel steering with autopilot. VC-17 bottom, painted teak trim. Annual maintenance by Crowley's Yacht Yard. Good sail inventory. Easy to sail single-handed. 16,000
30 Irwin 1976 Grandyear Excellent choice for the casual day-sailor on a budget, this is a good old boat that has been faithfully maintained. Roomy cockpit, wide walkways, and ample interior volume. New sails in 2013. 4,900
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 SOLD
31 Capital Yachts Newport 31 1988 Sollevare Nice cruiser, sleeps 7. Autopilot. Wheel steering. Furling genoa. Lewmar winches: 3 regular & 2 self-tailing. SOLD
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. 15,000 UA
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
32 O'Day 32cc 1977 Kettle Ann Center cockpit. Two separate cabins. Regularly maintained. In-mast Roller Furling Mainsail. Dinghy davits. Canvas cockpit enclosure. Sails recently repaired, New halyards in 2013. New fuel tank in 2012. New winter cover in 2013. LED lighting throughout (new in 2016). New 2016 Garmin GPS Chartplotter with North America chip. Boat is loop ready! Completed the loop in August 2017. Very economical and comfortable way to do the loop.
Read a August 2017 article about Kettle Ann. 15,900
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
33 Hunter 2011 Inner Peace One-owner, always fresh water sailed on Lake Michigan. Very well maintained; oil changed at the beginning, middle, and end of every season. New UK mainsail in 2016. Central air conditioning and heat. Electric flush head. Lewmar folding wheel. Yanmar 29hp diesel engine. Raymarine ST-60 depth and speed. Refrigerator and freezer. 105,000
33 Tartan T-10 1984 Druid At Crowley's yacht Yard. Available mid-September. 19,000
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 SOLD
34 C&C 34 1982 Marinochka Major restoration on this well-equipped, racer/cruiser. Complete new Awlgrip job in 2014; hull, deck and non-skid prepped, primed and painted, deck hardware re-bedded. Smooth VC17 bottom painted annually. Yanmar diesel engine. New transmission in 2014. Wheel steering, autopilot, Harken roller furling. All new electronics in 2015. New rudder in 2016. Always in fresh water, Lake Michigan. Reupholstered cushions, new windows, new folding prop. Beautiful teak-and-holly sole. 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. 19,000
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. SOLD
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 Hallberg-Rassy Rasmus 35 1976 Annabelle The Rasmus 35 was designed by the leading Swedish yacht designer of the 1960s, Olle Enderlein. 760 boats were made between 1967 and 1978. The design of the Rasmus 35 was in many ways ahead of its time. It was the first sailing yacht in the world with a windscreen. Annabelle features a new Simrad autopilot. The engine is a Volvo Penta MD-21 which needs work. The engine is currently non-operational. 10,000 UA
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. Major update ($21,000+) of electronics in 2016. 42,500
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 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. 21,000
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
36 Sabre Custom 1987 Probe Well maintained custom one-off racer cruiser. Comfortable cruising interior. 6' 2" headroom. Wheel steering.
Marine Survey
Builder's Notes 59,500
37 Irwin 1972 Jung Frau Always fresh water sailed on Lake Michigan. Winterized annually, new bottom paint annually. New mainsail and jib in 2016.
Rig Inspection Report 11,995
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 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

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.	47,000
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	Sabre	1978	Island Sunset	Lake Michigan cruised, well maintained classic Sabre 28. Sturdy boat, diesel engine, roller furling, wheel steering with autopilot. VC-17 bottom, painted teak trim. Annual maintenance by Crowley's Yacht Yard. Good sail inventory. Easy to sail single-handed.	16,000
30	Irwin	1976	Grandyear	Excellent choice for the casual day-sailor on a budget, this is a good old boat that has been faithfully maintained. Roomy cockpit, wide walkways, and ample interior volume. New sails in 2013.	4,900
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	SOLD
31	Capital Yachts Newport 31	1988	Sollevare	Nice cruiser, sleeps 7. Autopilot. Wheel steering. Furling genoa. Lewmar winches: 3 regular & 2 self-tailing.	SOLD
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.	15,000 UA
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
32	O'Day 32cc	1977	Kettle Ann	Center cockpit. Two separate cabins. Regularly maintained. In-mast Roller Furling Mainsail. Dinghy davits. Canvas cockpit enclosure. Sails recently repaired, New halyards in 2013. New fuel tank in 2012. New winter cover in 2013. LED lighting throughout (new in 2016). New 2016 Garmin GPS Chartplotter with North America chip. Boat is loop ready! Completed the loop in August 2017. Very economical and comfortable way to do the loop. Read a August 2017 article about Kettle Ann.	15,900
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
33	Hunter	2011	Inner Peace	One-owner, always fresh water sailed on Lake Michigan. Very well maintained; oil changed at the beginning, middle, and end of every season. New UK mainsail in 2016. Central air conditioning and heat. Electric flush head. Lewmar folding wheel. Yanmar 29hp diesel engine. Raymarine ST-60 depth and speed. Refrigerator and freezer.	105,000
33	Tartan T-10	1984	Druid	At Crowley's yacht Yard. Available mid-September.	19,000
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	SOLD
34	C&C 34	1982	Marinochka	Major restoration on this well-equipped, racer/cruiser. Complete new Awlgrip job in 2014; hull, deck and non-skid prepped, primed and painted, deck hardware re-bedded. Smooth VC17 bottom painted annually. Yanmar diesel engine. New transmission in 2014. Wheel steering, autopilot, Harken roller furling. All new electronics in 2015. New rudder in 2016. Always in fresh water, Lake Michigan. Reupholstered cushions, new windows, new folding prop. Beautiful teak-and-holly sole.	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.	19,000
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.	SOLD
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	Hallberg-Rassy Rasmus 35	1976	Annabelle	The Rasmus 35 was designed by the leading Swedish yacht designer of the 1960s, Olle Enderlein. 760 boats were made between 1967 and 1978. The design of the Rasmus 35 was in many ways ahead of its time. It was the first sailing yacht in the world with a windscreen. Annabelle features a new Simrad autopilot. The engine is a Volvo Penta MD-21 which needs work. The engine is currently non-operational.	10,000 UA
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. Major update ($21,000+) of electronics in 2016.	42,500
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	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.	21,000
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
36	Sabre Custom	1987	Probe	Well maintained custom one-off racer cruiser. Comfortable cruising interior. 6' 2" headroom. Wheel steering. Marine Survey Builder's Notes	59,500
37	Irwin	1972	Jung Frau	Always fresh water sailed on Lake Michigan. Winterized annually, new bottom paint annually. New mainsail and jib in 2016. Rig Inspection Report	11,995
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	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

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