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

Brokerage Sailboats

Listings Updated 09/15/23

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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= Marine Survey and/or Mechanical Systems Evaluation Report available.
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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
30 Catalina 30TR 1986 Stormy Well maintained Lake Michigan boat. 4 owners since new. 6' interior headroom. 23,000
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 Hunter 33 2005 20-20 Foresight This one owner boat has always been sailed in Chicago. Every year since new she has been stored indoors cold storage over the winter. The Yanmar 3YM30G has been professionally maintained by Crowley's Yacht Yard in Chicago. Taking its celebrated hull design from the proven running bottoms of its larger 41- and 44-foot sisterships, the Hunter 33 imparts the best in performance without compromising one inch of interior space, resulting in a top-of-the-line midsize cruiser that has it all. SOLD
33 Dufour 325 Grand Large 2007 Peony The 325 is a sleek looking coastal cruiser with generous interior and storage space for a 32-footer. Also features a roomy cockpit with teak seats and leather wrapped lewmar wheel. Raymarine instruments and chartplotter. SOLD
34 Olson 34 1989 Shoe String The Olson 34 is fantastic racer-cruiser. A medium weight boat that wins on the race course and doubles as a family cruiser. Shoe String is turn-key with a phenomenal sail inventory; brand new in 2022 UK 3DL Main and Genoa, as well as a complete inventory of racing jibs and spinnakers and Trogear carbon bowsprit. SOLD
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. 37,000
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. 78,000UA
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. 92,000
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. 65,000
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. 195,000
40 Beneteau Oceanis 40 2010 Makani U'I Best Midsize Cruiser in Cruising World's 2008 Boat of the Year contest, and with good reason. Below deck joinery is beautiful; soft and warm, but plenty of light for the perfect mix of classic and modern styling. Makani U'I features the tall rig and 5' 9" draft. Performance sails including a Kevlar main. 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. 225,000
44 Nautor Swan 44 MKII 2000 18 Degrees The Swan 44 MK II was designed by German Frers and built by Nautor. This boat has exceptional sailing performance and luxurious accommodations below decks. The large cockpit is popular with cruisers and racers alike. 18 Degrees has been meticulously maintained and underwent an $85K+ refit in 2021 - 2022. SOLD

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