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

Brokerage Sailboats

Listings Updated 07/02/24

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 Pearson 28 1980 Island Time Island Time has seen very casual daysailing off the Chicago lakefront. A classic Bill Shaw design. She has a Universal 11hp diesel engine. The last 20 years she has recieved meticulous service. The decks were professionally checked and in great condition of fall 2023. 9,900
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 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. SOLD
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 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 Hunter 34 1983 Dream Catcher Dream Catcher has always been a Chicago lakefront day sailed boat. Good bottom and keel-hull joint; rudder and decks, main bulkhead and compression post all seem solid, good opportunity for a DIY’er who wants a popular 34 footer with good bones at affordable price. 11,000
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. 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. 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. SOLD
36 S2 11.0A 1981 Voyager Voyager has spent more than 25 years on the coast of Maine and experienced all types of wind, weather, and sea states - proving its sea worthiness. She also have exceptional solid teak interior. The surveyed vessel was found to be in above average condition and to be adequately equipped for cruising and weekend live aboard conditions. SOLD
36 Catalina 36MKII 2001 Galt's Gulch This day sailed Lake Michigan boat is a beauty! Galt's Gulch is as turn-key ready as it gets! She is currently available for showings in St. Joe, Michigan. On July 13th she will be sailed to Chicago and be available for showings at Crowley's Yacht Yard. 85,000
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. 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
40 Beneteau Oceanis 40 2008 Normandie II A lightly used beautiful cruising boat with many cruising amenities.  A new navy blue Bimini was installed in February of 2024 by Chicago Marine Canvas. Her off-season storage has been in an inside heated storage unit. Boat is in great condition and should give many years of good service! 160,000
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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