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 06/10/21

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 Chip Stulen Faering Design 1987 Passasje Gorgeous and unique hand-made wooden boat, custom built by Chip Stulen. 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. 48,000
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. 4,000
30 Cape Dory 30 Cutter 1982 Scout Safe, reliable full-keel boat for mellow sailing. New Yanmar diesel in 2009. Wheel steering. Roller furling. New genoa in 2016. 22,500
30 Pearson 303 1983 Eternal Optimist Very clean, well maintained inside and out, Lake Michigan day-sailed boat. No damage. Only 3 owners since new. Edson wheel steering, Yanmar diesel, Harken roller furling, Raymarine ST6002 autopilot. Sleeps 5 adults; 6' 3" cabin headroom. 21,000
31 Hunter 310 1999 Worry Free Two private staterooms. Large cockpit. Integrated arch. B&R fractional rig. 38,000
32 Westsail 32 1973 Gallant Exclusively fresh water sailed since 2004. Stored indoors heated over winters since 2004. New in June 2016: Beta 38hp diesel engine, wiring, hoses, 3-blade bronze prop, TMC 60 transmission, and (2) 40 gallon custom fuel tanks. New 2014: Force 10 propane 2-burner stove w/ oven. (2) bilge pumps, (2) VHF radios, Garmin GPS, B&G Multi. SOLD
33 Beneteau 331 2003 Belfree Very well cared-for, always fresh water 1-owner boat. Lightly daysailed summers in Lake Michigan. 64,000
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 33.5 1992 Kiley Ann Two owner, Lake Michigan lightly sailed, well maintained boat. Autopilot, radar, roller furling, full-batten mainsail with Jiffy reefing and lazy jacks, central air conditioning, folding wheel. SOLD
36 Beneteau First 36.7 2006 Lazy Lightning Low hours. Excellent condition. 99,000
36 Catalina 36 MKII 1995 Ariel Always fresh water sailed. Central air-conditioning and heat. Autopilot. Main with Dutchman. Furling genoa. SOLD
37 Baltic 37 1979 Grand Vitesse This is a true racer/cruiser The tri-cabin arraignment with solid doors affords unusual privacy for a 37 foot boat. She is well outfitted and ready to sail anywhere. New Volvo saildrive in 2019. Newer 18,000 btu heat and air conditioning. Newer ultrasuede microfiber cushions. Newer electronics.
Baltic 37 Manufacturer Specs 40,000
37 Beneteau 373 2005 The Last One Well maintained, lightly cruised Lake Michigan sailboat, shrink-wrapped over winters. SOLD
38 Cabo Rico 38 Cutter 1967 Deme Coming soon to Crowley's Yacht Yard. Call for details.
May 2021 marine survey
May 2021 marine survey photos 38,000
38 Catalina 380 1999 Yapuda Fresh water only, and only 2 owners since new. Beautiful custom solid teak flooring, stainless steel delta anchor, power winch for mainsail hoisting, auto-prop, pro-furl boom, updated interior cushions, custom fixtures for easy winterizing, air-conditioning, sound-proofed engine compartment, lazarette gas shocks, and more. Add in her tall mast option and fin keel, 7' 2" draft, and you have a true sailor’s sailboat. You don’t want to miss this one.
Yapuda January 2021 Rigging Report 105,000 UA
39 Bristol 39 1967 4 Winds Three owner boat. Current owner owned boat for ~30 years in Chicago. Original Graymarine 31hp engine was rebuilt in 1995. Covered with a tarp over winters. 16,000
40 Jeanneau Sun Odyssey 40.3 2006 Perfect World Very well maintained, always fresh water sailed, stored indoor heated over winters. Stiff, responsive and balanced under sail, the Sun Odyssey 40.3 can easily be handled short-handed. SOLD
45 Jeanneau Sun Odyssey 45 DS 2008 Magellan Beautiful, well-maintained boat. Dual steering wheels. Furling main and genoa. 3 electric winches. Electric windlass. 2 electric flush heads. New North Sails main and genoa in June 2020. Heat and A/C (2 units). Bow thruster. SOLD
74 Custom Staysail Schooner Nils Lucander Design 2013 Lucander World Class Cruising Sailboat Project (Unfinished). Build the Sailboat of Your Dreams. This 74 Staysail Schooner, named Albacore, is more than one-half complete, constructed out of premium steel and stainless steel. Price includes professional blueprints originally designed by Nils Lucander, Marine & Yacht Design,TacomaWA 98407, Design #303. 125,000

LOA	Type	Year	Name	Remarks	Price
20	Chip Stulen Faering Design	1987	Passasje	Gorgeous and unique hand-made wooden boat, custom built by Chip Stulen. 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.	48,000
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.	4,000
30	Cape Dory 30 Cutter	1982	Scout	Safe, reliable full-keel boat for mellow sailing. New Yanmar diesel in 2009. Wheel steering. Roller furling. New genoa in 2016.	22,500
30	Pearson 303	1983	Eternal Optimist	Very clean, well maintained inside and out, Lake Michigan day-sailed boat. No damage. Only 3 owners since new. Edson wheel steering, Yanmar diesel, Harken roller furling, Raymarine ST6002 autopilot. Sleeps 5 adults; 6' 3" cabin headroom.	21,000
31	Hunter 310	1999	Worry Free	Two private staterooms. Large cockpit. Integrated arch. B&R fractional rig.	38,000
32	Westsail 32	1973	Gallant	Exclusively fresh water sailed since 2004. Stored indoors heated over winters since 2004. New in June 2016: Beta 38hp diesel engine, wiring, hoses, 3-blade bronze prop, TMC 60 transmission, and (2) 40 gallon custom fuel tanks. New 2014: Force 10 propane 2-burner stove w/ oven. (2) bilge pumps, (2) VHF radios, Garmin GPS, B&G Multi.	SOLD
33	Beneteau 331	2003	Belfree	Very well cared-for, always fresh water 1-owner boat. Lightly daysailed summers in Lake Michigan.	64,000
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 33.5	1992	Kiley Ann	Two owner, Lake Michigan lightly sailed, well maintained boat. Autopilot, radar, roller furling, full-batten mainsail with Jiffy reefing and lazy jacks, central air conditioning, folding wheel.	SOLD
36	Beneteau First 36.7	2006	Lazy Lightning	Low hours. Excellent condition.	99,000
36	Catalina 36 MKII	1995	Ariel	Always fresh water sailed. Central air-conditioning and heat. Autopilot. Main with Dutchman. Furling genoa.	SOLD
37	Baltic 37	1979	Grand Vitesse	This is a true racer/cruiser The tri-cabin arraignment with solid doors affords unusual privacy for a 37 foot boat. She is well outfitted and ready to sail anywhere. New Volvo saildrive in 2019. Newer 18,000 btu heat and air conditioning. Newer ultrasuede microfiber cushions. Newer electronics. Baltic 37 Manufacturer Specs	40,000
37	Beneteau 373	2005	The Last One	Well maintained, lightly cruised Lake Michigan sailboat, shrink-wrapped over winters.	SOLD
38	Cabo Rico 38 Cutter	1967	Deme	Coming soon to Crowley's Yacht Yard. Call for details. May 2021 marine survey May 2021 marine survey photos	38,000
38	Catalina 380	1999	Yapuda	Fresh water only, and only 2 owners since new. Beautiful custom solid teak flooring, stainless steel delta anchor, power winch for mainsail hoisting, auto-prop, pro-furl boom, updated interior cushions, custom fixtures for easy winterizing, air-conditioning, sound-proofed engine compartment, lazarette gas shocks, and more. Add in her tall mast option and fin keel, 7' 2" draft, and you have a true sailor’s sailboat. You don’t want to miss this one. Yapuda January 2021 Rigging Report	105,000 UA
39	Bristol 39	1967	4 Winds	Three owner boat. Current owner owned boat for ~30 years in Chicago. Original Graymarine 31hp engine was rebuilt in 1995. Covered with a tarp over winters.	16,000
40	Jeanneau Sun Odyssey 40.3	2006	Perfect World	Very well maintained, always fresh water sailed, stored indoor heated over winters. Stiff, responsive and balanced under sail, the Sun Odyssey 40.3 can easily be handled short-handed.	SOLD
45	Jeanneau Sun Odyssey 45 DS	2008	Magellan	Beautiful, well-maintained boat. Dual steering wheels. Furling main and genoa. 3 electric winches. Electric windlass. 2 electric flush heads. New North Sails main and genoa in June 2020. Heat and A/C (2 units). Bow thruster.	SOLD
74	Custom Staysail Schooner Nils Lucander Design	2013	Lucander	World Class Cruising Sailboat Project (Unfinished). Build the Sailboat of Your Dreams. This 74 Staysail Schooner, named Albacore, is more than one-half complete, constructed out of premium steel and stainless steel. Price includes professional blueprints originally designed by Nils Lucander, Marine & Yacht Design,TacomaWA 98407, Design #303.	125,000

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