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

Brokerage Sailboats

Listings Updated 05/18/22

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 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
28 Cal 28 1988 Seventh Heaven Well maintained, always Lake Michigan sailed boat. Yanmar 18hp diesel. Wheel steering. 20,000
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. 16,000UA
30 Hunter 30 1993 The Verdict Well maintained regularly by owner and Crowley's Yacht Yard. 2 owners since new. Stored over winters outdoors. Always fresh water sailed on Lake Michigan. Spacious T-shaped cockpit with five lockers. Helm seat removes for access to walk-through transom and swim platform. New mainsail in 2019. 24,000
30 Catalina 30TR 1991 Defiant Well-maintained Lake Michigan boat. Bottom in excellent condition. This boat has had two owners; current owner since 1996. Annual maintenance performed by Chicago's premier yacht yard. Only 608 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. SOLD
30 Catalina 30TR 1991 Fellowship Fellowship is a tall rig Catalina 30 with walkthrough transom. More details coming soon! 29,900
30 Allied Seawind 1969 Zvirbulis Ketch design used for day sailing in Chicago and light cruising on Lake Michigan. Well maintained at Crowley's Yacht Yard for 20+ years with maintenance records back to 2012. 12,000
30 Nonsuch 30 Ultra 1987 Bustopher Jones Bustopher Jones is a 1987 Nonsuch 30 Ultra with shallow draft.
Nonsuch Marketing Videos
30 Nonsuch 30 Ultra 1986 Peace on Earth Fresh water sailed since 2006. New in 2008 Raymarine instruments. Autohelm Smartpilot 6002 and Garmin 2010c GPSmap w/ Lake Michigan chart. EPIRB. Lewmar folding wheel. Walker Bay 8' dinghy.
Nonsuch Marketing Videos
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. 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 Sea Sprite 1983 Toy Soldier The Sea Sprite 34 is a classic cruising sailboat. Toy Soldier is hull #27, built by C.E. Ryder in Bristol Rhode Island in 1983 and was designed by Bill Luders 55,000
34 Beneteau 345 1986 Decision Decision has as far as we know always been a fresh water sailed boat. She is overall in very good condition; decks solid underfoot with no crazing, topsides and waterline stripe are clean and free of scrapes and scratches, VC-17 bottom in excellent condition; rudder is smooth on both sides & shows no signs of failure. Over the last 18 years all but two years Decision has been stored in heated and unheated buildings at the premiere Chicago boatyard. SOLD
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
34 Ericson 34T 1979 Kraken 1979 Tall Rig, Trunk Cabin competitive racer/cruiser. Over the past 7 years, this boat was meticulously and wonderfully refitted and refreshed by her owners. Kraken also has a full inventory of 12 racings sails - details on age/make/type coming soon 16,500
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
36 Beneteau Oceanis 36 Center Cockpit 2000 Against The Wind Always fresh water boat. Low engine hours. Brand new furling main sail. Electric windlass. Furling Genoa. Raymarine instruments. Autohelm 4000+ autopilot. 79,900UA
36 Ericson 36 1980 Wavelength Wavelength appears to be an always-fresh-water sailed Ericson 36. New diesel engine 2012. Autopilot, wheel steering, KVH electronics; VHF ship-to-shore radio and Raymarine GPS, dodger & bimini, double spreader rig, Harken furling, spinnaker gear, Harken mainsheet traveler. 21,000
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. 16,000UA
40 Beneteau First 40.7 2002 Mojo Well maintained, always fresh water cruised and raced in Lake Michigan. 115,000

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