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

Brokerage Sailboats

Listings Updated 03/30/23

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

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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 Schock Harbor 25 2010 Tecumseh Tecumseh is a well maintained example of this lively day-sailor from Schock W.D. She features two single berths, a marine head and 12.5 hp Honda sail drive auxiliary. The jib boom makes single-hand sailing a breeze. 54,500
28 Ericson 28-2 1988 Imjatse 2 owner Ericson 28-2. Always fresh water sailed in Chicago. Shrink-wrapped mast up at Crowley's Yacht Yard. 14,000
30 Catalina 30TR 1982 Nittany Clean updated example of Catalina's most popular model ever. Tall rig. More details to follow. 14,000
30 Catalina 30TR 1989 Intention One owner last 7 years. This has always been a fresh water boat. Sailed and raced on Lake Michigan. 2021 Midwest Open Racing Fleet Boat of the Year (MORF). Bottom painted every spring (VC17). Shrink wrapped every winter. Performance sails and standard Catalina sails. Brand new Harken roller furler in 2022. SOLD
30 Catalina 30TR 1986 Stormy Well maintained Lake Michigan boat. 4 owners since new. 6' interior headroom. 23,000
30 Catalina 30 1983 Sugaree Nice, standard rig Catalina 30. More details to follow. 18,000
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. 16,000
31 Catalina 309 2008 Feelin' Groovy Built as an update to the Catalina 30, one of the most successful production boats ever designed with a production run of over 30 years, you know the 309 has some very large shoes to fill. Luckily, it rises it to the occasion. It maintains the simple and practical layout that made the the C-30 a success, but incorporates modern trends with a wider beam that is carried aft resulting in a very roomy cockpit and a true aft cabin below deck. SOLD
31 Tartan 3100 1995 Komokwa Tartan's reputation for solid construction and good workmanship apparent in this well-maintained boat. As with most Tartan designs, the quality and finish of the 3100 is a cut above other of it's size and design from the period. Beautiful teak bulkheads, furniture, nav station, cabinets, toe rail and grab rails. Nice balance between performance sailing and cruising comfort. SOLD
32 Hunter 320 2001 Never Say Never Never Say Never is a two-owner, fresh water only boat. The Hunter 320 is as spacious and roomy as a 32-footer gets, both above, and below deck. She has always been professionally maintained by Crowley's Yacht Yard and stored outside shrink-wrapped.

Hunter 320: Thirty-two-footer on Steroids
32 Hunter 326 2003 Time Out The Hunter 326 is the perfect entry-level cruising boat for the sailor looking to move up from a twenty-something day or trailer sailer. She has an easily managed sail plan and all lines are lead back within arms reach of the helm. The cockpit and interior are both surprisingly roomy for a 32 footer. SOLD
32 O'Day 322 1987 Recess Comfortable and roomy boat has cruised the Great Lakes since new. Never in salt water. Wing keel with 4' 2" draft. Large cockpit; wheel steering; great interior layout with 6' 4" headroom; huge aft cabin; and a large enclosed head with shower. SOLD
32 Beneteau 32s5 1991 Au Revoir Wing keel version of this sleek 32 footer designed by Phillipe Stark and Berret-Racoupeau Yacht Design. Always fresh water sailed on Lake Michigan and Lake Carlyle. With a PHRF rating of 135 she's quick for her size and a great boat for Wednesday night racing, while also a perfectly capable cruiser, which has been her main use by her current owners who have lovingly cared for her the last 25 years 39,500
33 Endeavour 33 1984 Past Midnight Beautiful teak interior. The E33 is part of the second generation of Endeavour sailboats. With new racing rules and the desire by cruisers to sail faster, Endeavour began emphasizing larger, stronger, and faster designs. Past midnight is in great condition and features a Yanmar 3GMF diesel and Raymarine ST6000 autopilot. 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. SOLD
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. 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. SOLD
34 Olson 34 1989 Shoe String The Olson 34 is fantastic racer-cruiser. A medium weight boat that wins on the race course and doubles as a family cruiser. Shoe String is turn-key with a phenomenal sail inventory; brand new in 2022 UK 3DL Main and Genoa, as well as a complete inventory of racing jibs and spinnakers and Trogear carbon bowsprit. 42,000
34 Benteau 343 2006 Enough is Enough One owner, always fresh water sailed, Lake Michigan boat. Stored winters shrink-wrapped at Crowley's Yacht Yard in Chicago. Two-cabin model with private vee-berth and very large aft-cabin. Yanmar diesel engine. New Raymarine navigation system added 3 years ago. Furling main and genoa. Folding prop. Steel cradle. Hot & cold pressure water. At time of purchase refrigerator was replaced with an icebox, but original refrigerator is still in original packaging and conveys with the boat. SOLD
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. SOLD
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! SOLD
36 Sabre 36 1985 Zephyr Clean and well maintained 1985 Sabre 36. A classic racer cruiser known for its great build and finish quality. SOLD
36 Beneteau Oceanis 361 2004 Scout This late model Oceanis 361 has been gently used by her 2 previous owners, sailed exclusively on Lake Michigan. The Oceanis is a comfortable coastal cruiser, perfect for a family or couple. Additional details coming soon! SOLD
36 Beneteau First 36.7 2006 Lazy Lightning The Beneteau 36.7 is a quintessential racer-cruiser, making Lazy Lightning a great first boat to try your hand at one design sailing, but with the creature comforts that make for a solid coastal cruiser. She has a mix of both racing and cruising sails, including a furling jib. The current owner has made numerous updates, including most recently a brand new head, batteries and upped purchase on the adjustable backstay. 75,000
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 Shannon 37 Ketch 1987 Albatros Full keel centerboard. Ketch. Blue Awlgrip topsides. Diesel engine. Autopilot. In-mast furling main. Furling genoa. SOLD
40 Beneteau First 40.7 2002 Mojo Well maintained, always fresh water cruised and raced in Lake Michigan. 97,500
40 Beneteau Oceanis 40 2010 Makani U'I Best Midsize Cruiser in Cruising World's 2008 Boat of the Year contest, and with good reason. Below deck joinery is beautiful; soft and warm, but plenty of light for the perfect mix of classic and modern styling. Makani U'I features the tall rig and 5' 9" draft. Performance sails including a Kevlar main. SOLD
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
44 Nautor Swan 44 MKII 2000 18 Degrees The Swan 44 MK II was designed by German Frers and built by Nautor. This boat has exceptional sailing performance and luxurious accommodations below decks. The large cockpit is popular with cruisers and racers alike. 18 Degrees has been meticulously maintained and underwent an $85K+ refit in 2021 - 2022. SOLD

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