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Sailboat Sales Co - 3434 E. 95th St - Chicago Illinois 60617 - Phone 773.221.8880 |
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Brokerage SailboatsListings 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 any column header to sort the table, ascending or descending. |
Click on boat name to view complete specs with equipment list and photos. |
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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 | ![]() |
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 | SOLD | ![]() |
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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