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

Brokerage Sailboats

Listings Updated 01/25/22

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.

Click on any column header to sort the table, ascending or descending.
Click on boat name to view complete specs with equipment list and photos.
= Marine Survey and/or Mechanical Systems Evaluation Report available.
UA = Under Agreement

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
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
28 Cal 28 1988 Seventh Heaven Well maintained, always Lake Michigan sailed boat. Yanmar 18hp diesel. Wheel steering. 20,000
28 Sabre 28 1978 Island Sunset Lake Michigan cruised, well maintained classic Sabre 28. Sturdy boat, diesel engine, roller furling, wheel steering with autopilot. VC-17 bottom, painted teak trim. Annual maintenance by Crowley's Yacht Yard. Good sail inventory. Easy to sail single-handed. Price includes complete winterizing, shrink wrapping, and full winter storage (including launch) at Crowley's Yacht Yard in Chicago through May 2022. SOLD
30 Catalina 30 MKII tall rig 1989 Wild Thyme Always fresh water sailed boat. Only three owners. 1st owner stored the boat indoors every winter. 2nd owner bought the boat in the fall of 2004 and stored the boat outdoors under a custom winter canvas cover every year. Third owner bought boat in 2014 and also stored boat under canvas cover over winters. Boat has been consistently well maintained in excellent condition. This boat is fun and easy to sail with the help of the Autohelm 4000 autopilot and Hood Seafurl roller furling. Sails are new in 2008. Central air conditioning was added in 1999. SOLD
30 Catalina 30 TR 1986 Stormy Daniel's 1986 Catalina 30 TR listed November 2nd, 2021. Lake Michigan boat. 4 owners since new. Well maintained boat. 20,000
30 Pearson 303 1983 Eternal Optimist Very clean, well maintained inside and out, Lake Michigan day-sailed boat. No damage. Only 3 owners since new. Edson wheel steering, Yanmar diesel, Harken roller furling, Raymarine ST6002 autopilot. Sleeps 5 adults; 6' 3" cabin headroom. SOLD
32 Ericson 32-2 1975 Anodyne Current owner has maintained well. Extensive repairs and upgrades. Full interior/exterior re-upholstery (2018), new head holding system (2019), Deck and hull owner repainted. 1997 Yanmar diesel engine has been well maintained. Newer mainsail (2016), and genoa (2017). Multiple electronic upgrades. New rudder. Stored under cover in winter. 18,000
32 Pearson 323 1980 Wind & Spirit Gracious cruising sailboat from the 1980s. Used for day sailing in Chicago and light cruising on Lake Michigan. Volvo diesel. Wheel steering. Draft is 4' 5". SOLD
33 Canadian Sailcraft CS 33 1984 Punch Classic Canadian Sailcraft CS 33 in great condition. Recent upgrades in sails, instruments, cushions. Lake Michigan day-sailed boat. Current owner is 3rd owner. Professionally maintained. Stored indoors over winters. SOLD
33 Ranger 1971 Kozak Always Lake Michigan sailed. 2 owner boat. Current owner has owned the boat since 1978. Always covered over winters. Boat not launched in 2021. Boat is winterized and located on land this winter at Crowley's Yacht Yard, shrink wrapped with easy zipper door access. 12,000
34 J Boats J/105 2001 Black Diamond Always fresh water sailed in Lake Michigan and Lake Huron. Current owner is 2nd owner. Stored outside shrinkwrapped over winters. 82,000
36 Beneteau First 36s7 1996 Reckoning Always sailed in Lake Michigan. Beautiful bright airy interior. Professionally maintained by Crowley's Yacht Yard for the last 18 years. Stored outdoors shrink-wrapped over winters. SOLD
37 Beneteau 373 1982 Summer Home II Always fresh water sailed, two-owner, well maintained, lightly cruised Lake Michigan sailboat, custom winter cover. In-mast furling, bow thruster, central air-conditioning and heat. New mainsail and genoa in 2020. SOLD
37 Jeanneau Sun Odyssey 37 2004 Heartbreaker 2 cabin version. Newer air conditioning with reverse cycle heat. Autopilot. In-mast furling main, and furling genoa. Bimini. Shoal draft. SOLD
37 Shannon 37 Ketch 1987 Albatros Full keel centerboard. Ketch. Blue Awlgrip topsides. Diesel engine. Autopilot. In-mast furling main. Furling genoa. 84,000
38 Catalina 380 1999 School's Out Award winning design. Huge interior volume for entertaining. Tall rig; excellent sailing specs for lighter wind. Class A rating shows she will strong in a heavy wind. All fiberglass deck requires minimal maintenance. 1st 15 years in Lake Michigan; Charleston, SC for 4 years. Current owner brought her back to Lake Michigan for 2019 and 2020 seasons. Excellently maintained throughout. Located in Kenosha, Wisconsin. Please call for appointment.
April 2019 Marine Survey
39 Bristol 39 1967 4 Winds Three owner boat. Current owner owned boat for ~30 years in Chicago. Original Graymarine 31hp engine was rebuilt in 1995. Covered with a tarp over winters. 16,000
40 Beneteau First 40.7 2002 Mojo Well maintained, always fresh water cruised and raced in Lake Michigan. 118,500

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