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 01/12/21

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 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. 4,000
27 Catalina 27 1986 Out 'n 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. SOLD
28 Beneteau First 285 1997 Saint Germain 1992 Beneteau First 285 in excellent condition with many amenities including aft cabin, wheel steering, diesel engine, hot pressure water, shower, self tailing winches, dodger, bimini, etc... She is an excellent performer on the water and makes for a great daysailer or cruiser for overnight trips. She has been very well cared for, promising good times and great sailing for years to come. SOLD
28 Beneteau Oceanis 281 1995 Escape Very well maintained, lightly used, two-owner freshwater boat. Shallow draft, roller furling jib, and in-mast furling main. Newer sails. Wheel steering. Diesel engine. Shrink-wrapped over winters. SOLD
28 Beneteau Oceanis 281 1997 Bailed Out Lake Michigan sailed. Large private aft cabin. Wheel steering, diesel engine. New Raymarine autopilot in 2018. Good light and ventilation. Center dropleaf dining table. Stored shrink-wrapped over winters. 25,000
28 Cal 28 1988 Seventh Heaven Well maintained, always Lake Michigan sailed boat. Yanmar 18hp diesel. Wheel steering. 18,000
30 Catalina 30 MKII Tall Rig 1991 Limerick Comfortable cruiser. Sleeps 7. 6' headroom. Well maintained, fresh water, wing keel, tall rig, wheel steering, diesel engine. 25,000
30 Hunter 30 1993 After Ours Lightly used for weekend sailing, fresh water only. Well maintained regularly by Crowley's Yacht Yard. Stored over winters outdoors with canvas cover. SOLD
30 Sabre 30 1981 Hale Kai Very well maintained boat. Four berths. 6' headroom. Teak cabin sole. 2 burner stove. Hot and cold pressure water, enclosed head, wind instruments, Harken roller furling, wheel steering.
Sabre 30 Owners Manual 25,000
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. 48,000
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. 36,500
34 Tartan 3400 2008 Flash One-owner, always fresh water, always indoor heated storage, beautiful boat. Set up for easy handling cruising with self-tacking furling jib; full-batten mainsail; B&G wind instruments and autopilot. Keel stepped mast. Cockpit dodger. Two Harken self-tailing winches, (one electric). Stored winters in heated building at Crowley's Yacht Yard. 135,000
36 Beneteau First 36.7 2006 Lazy Lightning Low hours. Excellent condition. 99,000
36 Catalina 36 1983 Sailavie Tall mast. Roller furling genoa. All lines lead to cockpit for easy handling. Autohelm 3000. 12-ft. wide beam allows ample room in salon with amazing 6' 5" headroom. Dodger and bimini. Ready to sail. SOLD
36 Morris M36 2006 Helene Helene is a wonderful Morris M-36 with popular options such as teak decks, and a Leisurefurl mainsail. She has an air conditioner for keeping her cool and dehumidified at the dock in warmer climates and has been professionally maintained since built and has been sailed in fresh water since 2014. Beautifully cared for, she is only available as the owners are moving up to an M42. 335,000
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 46,000
37 Beneteau 373 2005 The Last One Well maintained, lightly cruised Lake Michigan sailboat, shrink-wrapped over winters. 98,000
37 Chris-Craft Apache 37 2005 Tomahawk Blends together good livability and a sea kindly motion, with a well performing hull and rig combination that can be single or shorthanded. Extremely safe even in inclement weather. “Tomahawk” has had three owners and resides on the cold, clean, freshwaters of Lake Michigan 18,000
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
39 C&C 37/40 XL 1993 Entropy New Yanmar diesel in 2018. Newer main and genoa. Electric winch (2012). Autohelm navcenter. Excellent racer/cruiser. Draft is 8' 2".
C&C Standard Equipment List 1993 SOLD
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. 129,500
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. 42,000
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. 210,000
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	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.	4,000
27	Catalina 27	1986	Out 'n 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.	SOLD
28	Beneteau First 285	1997	Saint Germain	1992 Beneteau First 285 in excellent condition with many amenities including aft cabin, wheel steering, diesel engine, hot pressure water, shower, self tailing winches, dodger, bimini, etc... She is an excellent performer on the water and makes for a great daysailer or cruiser for overnight trips. She has been very well cared for, promising good times and great sailing for years to come.	SOLD
28	Beneteau Oceanis 281	1995	Escape	Very well maintained, lightly used, two-owner freshwater boat. Shallow draft, roller furling jib, and in-mast furling main. Newer sails. Wheel steering. Diesel engine. Shrink-wrapped over winters.	SOLD
28	Beneteau Oceanis 281	1997	Bailed Out	Lake Michigan sailed. Large private aft cabin. Wheel steering, diesel engine. New Raymarine autopilot in 2018. Good light and ventilation. Center dropleaf dining table. Stored shrink-wrapped over winters.	25,000
28	Cal 28	1988	Seventh Heaven	Well maintained, always Lake Michigan sailed boat. Yanmar 18hp diesel. Wheel steering.	18,000
30	Catalina 30 MKII Tall Rig	1991	Limerick	Comfortable cruiser. Sleeps 7. 6' headroom. Well maintained, fresh water, wing keel, tall rig, wheel steering, diesel engine.	25,000
30	Hunter 30	1993	After Ours	Lightly used for weekend sailing, fresh water only. Well maintained regularly by Crowley's Yacht Yard. Stored over winters outdoors with canvas cover.	SOLD
30	Sabre 30	1981	Hale Kai	Very well maintained boat. Four berths. 6' headroom. Teak cabin sole. 2 burner stove. Hot and cold pressure water, enclosed head, wind instruments, Harken roller furling, wheel steering. Sabre 30 Owners Manual	25,000
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.	48,000
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.	36,500
34	Tartan 3400	2008	Flash	One-owner, always fresh water, always indoor heated storage, beautiful boat. Set up for easy handling cruising with self-tacking furling jib; full-batten mainsail; B&G wind instruments and autopilot. Keel stepped mast. Cockpit dodger. Two Harken self-tailing winches, (one electric). Stored winters in heated building at Crowley's Yacht Yard.	135,000
36	Beneteau First 36.7	2006	Lazy Lightning	Low hours. Excellent condition.	99,000
36	Catalina 36	1983	Sailavie	Tall mast. Roller furling genoa. All lines lead to cockpit for easy handling. Autohelm 3000. 12-ft. wide beam allows ample room in salon with amazing 6' 5" headroom. Dodger and bimini. Ready to sail.	SOLD
36	Morris M36	2006	Helene	Helene is a wonderful Morris M-36 with popular options such as teak decks, and a Leisurefurl mainsail. She has an air conditioner for keeping her cool and dehumidified at the dock in warmer climates and has been professionally maintained since built and has been sailed in fresh water since 2014. Beautifully cared for, she is only available as the owners are moving up to an M42.	335,000
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	46,000
37	Beneteau 373	2005	The Last One	Well maintained, lightly cruised Lake Michigan sailboat, shrink-wrapped over winters.	98,000
37	Chris-Craft Apache 37	2005	Tomahawk	Blends together good livability and a sea kindly motion, with a well performing hull and rig combination that can be single or shorthanded. Extremely safe even in inclement weather. “Tomahawk” has had three owners and resides on the cold, clean, freshwaters of Lake Michigan	18,000
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
39	C&C 37/40 XL	1993	Entropy	New Yanmar diesel in 2018. Newer main and genoa. Electric winch (2012). Autohelm navcenter. Excellent racer/cruiser. Draft is 8' 2". C&C Standard Equipment List 1993	SOLD
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.	129,500
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.	42,000
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.	210,000
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