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

Brokerage Sailboats

Listings Updated 08/15/22

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.

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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.
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. 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
30 S2 9.2A 1977 Right Time Right time is a well appointed S2 with two main sails, two jibs, and a spinnaker. Interior features easy access to engine and an updated galley with newer faucet and ample storage. Original manuals and documentation onboard. SOLD
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. SOLD
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! SOLD
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.
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30 Dufour Arpege 1972 Harizon Harizon is an excellent example of the most successful Dufour import; the Arpege 30. A small but sturdy, offshore capable, boat that can also impress on the race course. 25,000
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 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. 68,000
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. 75,000
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 34,000
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. 72,500UA
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 SOLD
35 O'Day 35 1985 La Bella Cosa This 3 owner O'Day 35 is in excellent condition. The topsides and cabin top are smooth and shiny. A racer cruiser with good sailing performance and roomy accommodations below.
35 Cal 35 MKII 1984 Sarah Bernadette The Cal 35 is a gorgeous, fast cruiser with traditional lines of her heyday that give her that timeless appeal. Sarah Bernadette is in great shape above and below decks: the hull has been buffed and waxed to a shiny, smooth finish and woodwork and cushions are in great shape below. She has a lot of toys and gadgets to monitor every system on the boat as well as new an array of newer Raymarine instruments. 26,000
35 Tartan 3500 2001 Fortunate 2 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. Fortunate 2's classic profile and flag blue hull will make her a head turner in any harbor! 125,000
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. SOLD
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. 12,000
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
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. 64,000 UA
40 Beneteau First 40.7 2002 Mojo Well maintained, always fresh water cruised and raced in Lake Michigan. 115,000
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. 225,000

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