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

Brokerage Sailboats

Listings Updated 02/17/21

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 Fairing Design 1987 Passasje Gorgeous and unique hand-made wooden boat, custom built by Chip Stuben. 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. 75,000
23 Irwin 1973 Sundog One owner since new. Sleeps 4. 5' 2" main cabin headroom. Retractable centerboard has been fixed in the up position for 25 years, sails well. Movement of centerboard can be restored if desired. New rudder in 2015. New teak in 2011. New sails in 2011. New outboard motor in 2009. 4,000
28 Beneteau Oceanis 281 1997 Bailed Out Lake Michigan sailed. Large private aft cabin. Wheel steering, diesel engine. New Raymarine autopilot in 2018. Good light and ventilation. Center dropleaf dining table. Stored shrink-wrapped over winters. 25,000 UA
28 Cal 28 1988 Seventh Heaven Well maintained, always Lake Michigan sailed boat. Yanmar 18hp diesel. Wheel steering. 18,000
30 Catalina 30 MKII Tall Rig 1991 Limerick Comfortable cruiser. Sleeps 7. 6' headroom. Well maintained, fresh water, wing keel, tall rig, wheel steering, diesel engine. 25,000
30 Sabre 30 1981 Hale Kai Very well maintained boat. Four berths. 6' headroom. Teak cabin sole. 2 burner stove. Hot and cold pressure water, enclosed head, wind instruments, Harken roller furling, wheel steering.
Sabre 30 Owners Manual
25,000 UA
32 Westsail 32 1973 Gallant Exclusively fresh water sailed since 2004. Stored indoors heated over winters since 2004. New in June 2016: Beta 38hp diesel engine, wiring, hoses, 3-blade bronze prop, TMC 60 transmission, and (2) 40 gallon custom fuel tanks. New 2014: Force 10 propane 2-burner stove w/ oven. (2) bilge pumps, (2) VHF radios, Garmin GPS, B&G Multi. 44,000
33 Bristol 1969 Sea Horse Sloop rig. Newer sails. Simrad autohelm (new - not installed). Tiller steering. Storage cradle. Universal Atomic 4 engine. 15,000
33 Hunter 33.5 1992 Kiley Ann Two owner, Lake Michigan lightly sailed, well maintained boat. Autopilot, radar, roller furling, full-batten mainsail with Jiffy reefing and lazy jacks, central air conditioning, folding wheel. 36,500
34 Tartan 3400 2008 Flash One-owner, always fresh water, always indoor heated storage, beautiful boat. Set up for easy handling cruising with self-tacking furling jib; full-batten mainsail; B&G wind instruments and autopilot. Keel stepped mast. Cockpit dodger. Two Harken self-tailing winches, (one electric). Stored winters in heated building at Crowley's Yacht Yard. 131,000
36 Beneteau First 36.7 2006 Lazy Lightning Low hours. Excellent condition. 99,000
36 Morris M36 2006 Helene Helene is a wonderful Morris M-36 with popular options such as teak decks, and a Leisurefurl mainsail. She has an air conditioner for keeping her cool and dehumidified at the dock in warmer climates and has been professionally maintained since built and has been sailed in fresh water since 2014. Beautifully cared for, she is only available as the owners are moving up to an M42. 335,000
37 Baltic 37 1979 Grand Vitesse This is a true racer/cruiser The tri-cabin arraignment with solid doors affords unusual privacy for a 37 foot boat. She is well outfitted and ready to sail anywhere. New Volvo saildrive in 2019. Newer 18,000 btu heat and air conditioning. Newer ultrasuede microfiber cushions. Newer electronics.
Baltic 37 Manufacturer Specs
37 Beneteau 373 2005 The Last One Well maintained, lightly cruised Lake Michigan sailboat, shrink-wrapped over winters. 98,000
37 Chris-Craft Apache 37 2005 Tomahawk Blends together good livability and a sea kindly motion, with a well performing hull and rig combination that can be single or shorthanded. Extremely safe even in inclement weather. “Tomahawk” has had three owners and resides on the cold, clean, freshwaters of Lake Michigan 19,000
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 Jeanneau Sun Odyssey 40.3 2006 Perfect World Very well maintained, always fresh water sailed, stored indoor heated over winters. Stiff, responsive and balanced under sail, the Sun Odyssey 40.3 can easily be handled short-handed. 129,500
42 Palmer Johnson Peterson 2-ton 1977 Sleeping Bear Always fresh water sailed, custom Peterson design that has been modified to provide comfortable cruising accommodations along with short handed sailing capability. Safety, convenience and performance in a well maintained, economical and pleasing vessel. New engine in 2007. 42,000
45 Jeanneau Sun Odyssey 45 DS 2008 Magellan Beautiful, well-maintained boat. Dual steering wheels. Furling main and genoa. 3 electric winches. Electric windlass. 2 electric flush heads. New North Sails main and genoa in June 2020. Heat and A/C (2 units). Bow thruster. 210,000 UA
74 Custom Staysail Schooner Nils Lucander Design 2013 Lucander World Class Cruising Sailboat Project (Unfinished). Build the Sailboat of Your Dreams. This 74 Staysail Schooner, named Albacore, is more than one-half complete, constructed out of premium steel and stainless steel. Price includes professional blueprints originally designed by Nils Lucander, Marine & Yacht Design,TacomaWA 98407, Design #303. 125,000

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