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 04/18/24

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.

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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 Picture
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
25 Maree Haute Django 7.70 2019 Baba Single keel, double rudder version of the Django 7.70, from French builder Marée Haute. The boat is easily single or double-handed as all line are led aft to the coach roof. Electric Torqeedo engine. Sailed in Chicago since new. 75,000

28 Hunter 280 1996 Salem Clean, well maintained example of the popular Hunter 280. As with many Hunter designs, the 280 elegantly incorporates features and accommodations usually reserved for boats several feet longer, such as 6' headroom, a roomy interior with large head/shower, and a walk-thru swim platform. SOLD

28 Catalina 28 MKII 2005 Summertime Summertime is a two owner boat; her first owner was out of Indianapolis he knew he wanted to sail throughout the Great Lakes so he had the custom Triad tandem trailer built he did in fact use the boat as far away as the North Channel Summertime has always been stored outside shrinkwrapped SOLD
28 Ericson 28-2 1989 Rozinante A well maintained and updated classic Ericson 28. Only 3 owners since new. Updated instruments and other onboard equipment. Engine professionally maintained and inspected annually. Winter storage covered outside or inside. SOLD
30 Catalina 30TR 1986 Stormy Stormy is an always fresh water 1986 Catalina 30 tall right and fin keel. Updated 150% genoa and harken roller furling. She has stak pack and lazy jacks. Bulkhead mount table layout. The owner has purchased his next boat so seriously for sale! 18,000
30 Catalina 30TR 1991 Defiant Well-maintained Lake Michigan boat. Bottom in excellent condition. This boat has had three owners; current owner since 2024. Annual maintenance performed by Chicago's premier yacht yard. Only 600+ hours on the original Universal M25 engine. Three blade max prop. Raymarine instruments. Adjustable backstay. One regular and five self-tailing winches. Wheel steering system. Sail inventory includes mainsail (original), 150% UK genoa (5 yrs), and an asymmetrical spinnaker (original). Includes Harken roller furler. This one is a beauty. It's in great condition inside and out! SOLD
30 Catalina 30TR 1989 Rita Marie Comfortable cruiser. Sleeps 7. 6' headroom. Rita Marie is in excellent overall condition, professionally maintained, fresh water, wing keel, tall rig, and wheel steering. There hasn't been a more popular or better suited starter boat produced than the Catalina 30. Comfortable and incredibly roomy for it's length this tall rig model does not compromise on performance either! New 2021 Genoa. Sail inventory also includes and asym spinnaker. SOLD
30 Yankee 30 1973 Owen Meany This Sparkman & Stephens designed racer/cruiser is a true classic. While in production for only 5 years it was built to the high quality standards of Yankee Yachts. 10,000
31 Beneteau First 305 1985 Panacea A 1985 sail-racer/cruiser Beneteau First 305 designed by Beret. Panacea has only had 1 owner and has been a Lake Michigan boat her whole life. VC17 bottom is in very good condition. Panacea needs engine work or replacement. 24,000
31 Pearson 31-2 1988 Inspiration Inspiration is an ‘88 standard draft fin keel Pearson 31-2 designed by the renowned American naval architect Bill Shaw; always fresh water sailed; Yanmar diesel, smooth VC-17 bottom, topsides washed, buffed and waxed on a regular basis, clean crisp updated North sails, Raymarine GPS/chartplotter and MFD boat and windspeed, depth. SOLD
33 Tartan 10 1980 Proving Run Classic Tartan racing sloop. SOLD
33 Pearson 33 1971 Margaritaville This lovingly and expertly maintained Pearson 33 is a near perfect example of Bill Shaw's classic design. Margaritaville's current owner has made a multitude of improvements and modernizations to the boat, while maintaining its classic appeal. This include repowering the boat with a Yanmar 3YM20. SOLD
34 Catalina 34 MKII 2002 Timoleague This Catalina 34 MKII is about as spacious a cruiser as you can get under 36 feet, and she has all the amenities of larger cruising boats; such as hot water, a swim platform, large aft berth, Air Conditioning, and an enormous cockpit. Very low hours on the professionally maintained M35B. SOLD
34 Hunter 340 1998 Cor de Rosa Cor De Rosa is a wonderfully maintained boat. Turn-key ready to sail for your next cruising adventure. This Hunter 340 features air conditioning and heat, Raymarine EV-100 autopilot, new cockpit cushions, new salon cushions, and new Group 31 AGM batteries. This boat is currently stored at West Basin Marina in St. Joseph, MI. Overall maintained includes buffing, waxing 2 times annually. Annual oil change and biannual engine maintenance. New VC17 bottom paint in April of 2024. Comes with a full winter cover. 56,500
34 Catalina 34 1989 Nothing But Time This 3 owner Catalina 34 is a two-cabin layout and is very clean and in above average condition. If you are looking for a very clean Catalina 34 this boat is a must see and always been in fresh water. SOLD
35 Thomas 35 1990 Broderi Very well-kept and exclusively freshwater sailed 1990 Thomas 35; Designed by Graham & Schlageter and Lindy Thomas in 1988 for speed and comfort; T35 combines excellent performance with an extremely comfortable and well laid out interior. 49,500
35 Tartan 3500 1993 Blue Moon The Tim Jacket designed Tartan 3500 was an incredibly successful model for the builder, and with good reason! She is an ideal cruiser for a couple or family. The 3500 is capable and comfortable without compromising performance. Blue Moon's classic profile will make her a head turner in any harbor! SOLD
35 Beneteau Oceanis 351 1996 Mar Nami This well maintained cruiser features brand new main and headsail and raymarine wireless wind instruments; turn-key boat in water at Belmont Harbor. SOLD
36 C&C 110 1999 Nancy Jo Tim Jacket designed 36' cruiser with the sleek and classic lines of C&C Yachts. Features a tapered 3 spreader rig with rod rigging, under-deck autopilot, and hot & cold pressure water. She is fully rigged for both symmetrical and asymmetrical spinnakers with a carbon spinnaker pole and a retractable Forespar carbon sprit. Roomy cockpit on deck and cherry wood joinery with teak & holly sole make for a comfortable and pleasing aesthetic below deck. SOLD
36 C&C 36XL 1996 Nebbiolo Fine example of the C&C 36 XL. Clean and well maintained. Nebbiolo has been exclusively freshwater cruised and raced, and kept off-season in indoor heated storage. Has Air Conditioning! Boat is currently in Montrose harbor. 63,000
36 Beneteau First 36.7 2006 Lazy Lightning The Beneteau 36.7 is a quintessential racer-cruiser, making Lazy Lightning a great first boat to try your hand at one design sailing, but with the creature comforts that make for a solid coastal cruiser. She has a mix of both racing and cruising sails, including a furling jib. The current owner has made numerous updates, including most recently a brand new head, batteries and upped purchase on the adjustable backstay. SOLD
37 Nautor Swan 37 1970 Dulcinea Dulcinea is hull 17 of the Swan 37 that dominated ocean racing in 1970-71. With her pronounced tumblehome and low windage profile, Dulcinea is a beautiful Sparkman & Stephens design with Nautor heirloom quality. Built in Finland of hand-laid solid fiberglass she has the classic S&S lead fin keel and separate skeg rudder that provides excellent upwind performance and fast, sea kindly passage making. SOLD
38 Beneteau Oceanis 38 2014 Quintessential II The Ocenanis 38 is a sleek, modern cruiser. Quintessential features the optional shallow draft and mainsail arch over the cockpit. Not to mention the beautiful gray gelcoat with a blue boot stripe that is sure to turn heads at the dock. SOLD
43 Alden Schooner 309 1929 Allegro Allegro is a 1929 John Alden schooner built by Goudy & Stevens. She is located in Chicago USA. Allegro spends her winters in a heat controlled building and summer on a mooring ball in Monroe Street Harbor. For the last 33 years Allegro has been lovingly maintained by the owner and professionally restored by expert shipwrights including Wayne Shibley of Chicago. 175,000

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
25	Maree Haute Django 7.70	2019	Baba	Single keel, double rudder version of the Django 7.70, from French builder Marée Haute. The boat is easily single or double-handed as all line are led aft to the coach roof. Electric Torqeedo engine. Sailed in Chicago since new.	75,000
28	Hunter 280	1996	Salem	Clean, well maintained example of the popular Hunter 280. As with many Hunter designs, the 280 elegantly incorporates features and accommodations usually reserved for boats several feet longer, such as 6' headroom, a roomy interior with large head/shower, and a walk-thru swim platform.	SOLD
28	Catalina 28 MKII	2005	Summertime	Summertime is a two owner boat; her first owner was out of Indianapolis he knew he wanted to sail throughout the Great Lakes so he had the custom Triad tandem trailer built he did in fact use the boat as far away as the North Channel Summertime has always been stored outside shrinkwrapped	SOLD
28	Ericson 28-2	1989	Rozinante	A well maintained and updated classic Ericson 28. Only 3 owners since new. Updated instruments and other onboard equipment. Engine professionally maintained and inspected annually. Winter storage covered outside or inside.	SOLD
30	Catalina 30TR	1986	Stormy	Stormy is an always fresh water 1986 Catalina 30 tall right and fin keel. Updated 150% genoa and harken roller furling. She has stak pack and lazy jacks. Bulkhead mount table layout. The owner has purchased his next boat so seriously for sale!	18,000
30	Catalina 30TR	1991	Defiant	Well-maintained Lake Michigan boat. Bottom in excellent condition. This boat has had three owners; current owner since 2024. Annual maintenance performed by Chicago's premier yacht yard. Only 600+ hours on the original Universal M25 engine. Three blade max prop. Raymarine instruments. Adjustable backstay. One regular and five self-tailing winches. Wheel steering system. Sail inventory includes mainsail (original), 150% UK genoa (5 yrs), and an asymmetrical spinnaker (original). Includes Harken roller furler. This one is a beauty. It's in great condition inside and out!	SOLD
30	Catalina 30TR	1989	Rita Marie	Comfortable cruiser. Sleeps 7. 6' headroom. Rita Marie is in excellent overall condition, professionally maintained, fresh water, wing keel, tall rig, and wheel steering. There hasn't been a more popular or better suited starter boat produced than the Catalina 30. Comfortable and incredibly roomy for it's length this tall rig model does not compromise on performance either! New 2021 Genoa. Sail inventory also includes and asym spinnaker.	SOLD
30	Yankee 30	1973	Owen Meany	This Sparkman & Stephens designed racer/cruiser is a true classic. While in production for only 5 years it was built to the high quality standards of Yankee Yachts.	10,000
31	Beneteau First 305	1985	Panacea	A 1985 sail-racer/cruiser Beneteau First 305 designed by Beret. Panacea has only had 1 owner and has been a Lake Michigan boat her whole life. VC17 bottom is in very good condition. Panacea needs engine work or replacement.	24,000
31	Pearson 31-2	1988	Inspiration	Inspiration is an ‘88 standard draft fin keel Pearson 31-2 designed by the renowned American naval architect Bill Shaw; always fresh water sailed; Yanmar diesel, smooth VC-17 bottom, topsides washed, buffed and waxed on a regular basis, clean crisp updated North sails, Raymarine GPS/chartplotter and MFD boat and windspeed, depth.	SOLD
33	Tartan 10	1980	Proving Run	Classic Tartan racing sloop.	SOLD
33	Pearson 33	1971	Margaritaville	This lovingly and expertly maintained Pearson 33 is a near perfect example of Bill Shaw's classic design. Margaritaville's current owner has made a multitude of improvements and modernizations to the boat, while maintaining its classic appeal. This include repowering the boat with a Yanmar 3YM20.	SOLD
34	Catalina 34 MKII	2002	Timoleague	This Catalina 34 MKII is about as spacious a cruiser as you can get under 36 feet, and she has all the amenities of larger cruising boats; such as hot water, a swim platform, large aft berth, Air Conditioning, and an enormous cockpit. Very low hours on the professionally maintained M35B.	SOLD
34	Hunter 340	1998	Cor de Rosa	Cor De Rosa is a wonderfully maintained boat. Turn-key ready to sail for your next cruising adventure. This Hunter 340 features air conditioning and heat, Raymarine EV-100 autopilot, new cockpit cushions, new salon cushions, and new Group 31 AGM batteries. This boat is currently stored at West Basin Marina in St. Joseph, MI. Overall maintained includes buffing, waxing 2 times annually. Annual oil change and biannual engine maintenance. New VC17 bottom paint in April of 2024. Comes with a full winter cover.	56,500
34	Catalina 34	1989	Nothing But Time	This 3 owner Catalina 34 is a two-cabin layout and is very clean and in above average condition. If you are looking for a very clean Catalina 34 this boat is a must see and always been in fresh water.	SOLD
35	Thomas 35	1990	Broderi	Very well-kept and exclusively freshwater sailed 1990 Thomas 35; Designed by Graham & Schlageter and Lindy Thomas in 1988 for speed and comfort; T35 combines excellent performance with an extremely comfortable and well laid out interior.	49,500
35	Tartan 3500	1993	Blue Moon	The Tim Jacket designed Tartan 3500 was an incredibly successful model for the builder, and with good reason! She is an ideal cruiser for a couple or family. The 3500 is capable and comfortable without compromising performance. Blue Moon's classic profile will make her a head turner in any harbor!	SOLD
35	Beneteau Oceanis 351	1996	Mar Nami	This well maintained cruiser features brand new main and headsail and raymarine wireless wind instruments; turn-key boat in water at Belmont Harbor.	SOLD
36	C&C 110	1999	Nancy Jo	Tim Jacket designed 36' cruiser with the sleek and classic lines of C&C Yachts. Features a tapered 3 spreader rig with rod rigging, under-deck autopilot, and hot & cold pressure water. She is fully rigged for both symmetrical and asymmetrical spinnakers with a carbon spinnaker pole and a retractable Forespar carbon sprit. Roomy cockpit on deck and cherry wood joinery with teak & holly sole make for a comfortable and pleasing aesthetic below deck.	SOLD
36	C&C 36XL	1996	Nebbiolo	Fine example of the C&C 36 XL. Clean and well maintained. Nebbiolo has been exclusively freshwater cruised and raced, and kept off-season in indoor heated storage. Has Air Conditioning! Boat is currently in Montrose harbor.	63,000
36	Beneteau First 36.7	2006	Lazy Lightning	The Beneteau 36.7 is a quintessential racer-cruiser, making Lazy Lightning a great first boat to try your hand at one design sailing, but with the creature comforts that make for a solid coastal cruiser. She has a mix of both racing and cruising sails, including a furling jib. The current owner has made numerous updates, including most recently a brand new head, batteries and upped purchase on the adjustable backstay.	SOLD
37	Nautor Swan 37	1970	Dulcinea	Dulcinea is hull 17 of the Swan 37 that dominated ocean racing in 1970-71. With her pronounced tumblehome and low windage profile, Dulcinea is a beautiful Sparkman & Stephens design with Nautor heirloom quality. Built in Finland of hand-laid solid fiberglass she has the classic S&S lead fin keel and separate skeg rudder that provides excellent upwind performance and fast, sea kindly passage making.	SOLD
38	Beneteau Oceanis 38	2014	Quintessential II	The Ocenanis 38 is a sleek, modern cruiser. Quintessential features the optional shallow draft and mainsail arch over the cockpit. Not to mention the beautiful gray gelcoat with a blue boot stripe that is sure to turn heads at the dock.	SOLD
43	Alden Schooner 309	1929	Allegro	Allegro is a 1929 John Alden schooner built by Goudy & Stevens. She is located in Chicago USA. Allegro spends her winters in a heat controlled building and summer on a mooring ball in Monroe Street Harbor. For the last 33 years Allegro has been lovingly maintained by the owner and professionally restored by expert shipwrights including Wayne Shibley of Chicago.	175,000

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