Sailboat Sales Co - 3434 E. 95th St - Chicago Illinois 60617 - Phone 773.221.8880



Brokerage Sailboats

Listings Updated 03/02/24

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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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. 15,000
30 Catalina 30TR 1986 Stormy Well maintained Lake Michigan boat. 4 owners since new. 6' interior headroom. 16,000
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! 35,000
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. 26,000
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
33 Tartan 10 1980 Proving Run Classic Tartan racing sloop. 15,000
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. 69,000UA
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. 78,000
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. 68,000
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 Jeanneau Sun Oddyssey 37 2004 Stormy Daniels II 2 cabin version. Newer air conditioning with reverse cycle heat. Autopilot. In-mast furling main, and furling genoa. Bimini. Shoal draft. Fabulous new marine decking installed in 2023. 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. 189,000UA
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





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