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



Brokerage Sailboats

Listings Updated 09/28/24

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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Click on boat name to view complete specs with equipment list and photos.
= Marine Survey and/or Mechanical Systems Evaluation Report available.
= Price recently reduced.
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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. SOLD
27 Catalina 27 1983 Wun-Len Wun-Len has been well maintained and kept in good condition, with many upgrades. She has been used for day sailing and cruising on Lake Michigan. 12,000
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
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
31 Beneteau First 305 1985 Panacea 1985 Beneteau First 305 designed by Beret. Panacea is a 1 owner boat sailing out of Chicago her whole life. Sails, rigging, decks, topsides, VC-17 bottom rudder and belowdecks all excellent. Recent c/v survey revealed no issues. Needs replacement engine; owner has a line on a 2010 Yanmar 20 hp with under 100 hrs and a capable marine diesel mechanic to do the install. 24,000
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 Elan Impression 34 2007 Flying Cloud Flying Cloud has always been a freshwater boat sailed on Lake Michigan. She has had excellent overall maintenance, and has lived indoors in a heated building during the winter months. 78,000
36 Hunter 36 2005 Serenity II Serenity II has been very well cared for and spent her life in freshwater. She has a salon area with two spacious cabins, head & shower and an excellent amount of storage space. 83,000
36 Jeanneau Sun Odyssey 37 2000 Creola II Creola II is a fresh water, gently used example of the popular Jeanneau Sun Odyssey 37. She is turn-key ready for her next owner. Current owners have had the vessel since 2005 and she has been stored shrink-wrapped in St. Joe MI over winters and had all annual maintenance and winterizations performed. Creolat features a fully battened mainsail with Dutchman, so you can experience all she has to offer without the performance compromise of the under-canvased in-mast furling models. Standard deep draft performance keel. An easy and fun boat for racing or double-handed cruising. Also features newer 135% Genoa and a .75 oz cruising spinnaker! 85,000
36 Catalina 36 1994 Anne Ellen Anne Ellen has been used for Great Lakes cruising. This Catalina is in above average condition with many upgraded items! She comes with a 4 pad steel cradle. 68,000
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. 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 Farr 38 1990 Radiance Radiance, a  Bruce Farr Yacht Design #72/2 built in 1990 in Rio de Janeiro to Lloyds standards. This renown graceful hull design & sail plan is beautifully balanced making her a joy to helm. She has had the good fortune of having only two owners and the current owner over the last 24 years has spent lavishly on her including a new Beta diesel engine, updated sails, standing & running rigging, electronics, deck hardware as well as maintaining the bottom, topsides and decks to high standards. Many boats much younger don’t look nearly as good. 49,500
40 Jeanneau Sun Odyssey 40.3 2007 Cherish the Day Cherish The Day has always been a freshwater, day sailed boat! She has been used as a time share with weekly maintenance. Lake Michigan is her home in the summer, and an indoor heated building has been her home in the winters. 143,000
40 Jeanneau Sun Odyssey 409 2015 Friendly Confines This Lake Michigan boat is performance oriented with cruising comfort! She has been professionally maintained and has had annual engine maintenance. 199,000
40 Beneteau Oceanis 40 2012 Superstition This Beneteau 40 has always been used for daysailing in Lake Michigan and is a great cruiser. Superstition has a brand new (2024) North Sails mainsail along with a like new Doyle APC gennaker. The Genoa halyard and all batteries were replaced in 2022/2023. She spends her off-season on an 8-post cradle and has been winterized by Crowley's Yacht Yard including the engine, water and holding tanks, and batteries. 175,000
42 Island Packet 38 1990 Seaquel This Island Packet has been a Lake Michigan, day sailed cruiser! She has had 2 owners and has had excellent engine and overall maintenance. 130,000
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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