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

Brokerage Sailboats

Listings Updated 07/27/21

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 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
30 Cape Dory 30 Cutter 1982 Scout Safe, reliable full-keel boat for mellow sailing. New Yanmar diesel in 2009. Wheel steering. Roller furling. New genoa in 2016. 22,500
30 Pearson 303 1983 Eternal Optimist Very clean, well maintained inside and out, Lake Michigan day-sailed boat. No damage. Only 3 owners since new. Edson wheel steering, Yanmar diesel, Harken roller furling, Raymarine ST6002 autopilot. Sleeps 5 adults; 6' 3" cabin headroom. 21,000
31 Hunter 310 1999 Worry Free Two private staterooms. Large cockpit. Integrated arch. B&R fractional rig. SOLD
33 Beneteau 331 2003 Belfree Very well cared-for, always fresh water 1-owner boat. Lightly daysailed summers in Lake Michigan. SOLD
33 Bristol 1969 Sea Horse Sloop rig. Newer sails. Simrad autohelm (new - not installed). Tiller steering. Storage cradle. Universal Atomic 4 engine. 15,000
36 Beneteau First 36.7 2006 Lazy Lightning Low hours. Excellent condition. 99,000
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
38 Catalina 380 1999 Yapuda Fresh water only, and only 2 owners since new. Beautiful custom solid teak flooring, stainless steel delta anchor, power winch for mainsail hoisting, auto-prop, pro-furl boom, updated interior cushions, custom fixtures for easy winterizing, air-conditioning, sound-proofed engine compartment, lazarette gas shocks, and more. Add in her tall mast option and fin keel, 7' 2" draft, and you have a true sailor’s sailboat. You don’t want to miss this one.
Yapuda January 2021 Rigging Report
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
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

All Rights Reserved, ©1996 - 2020 Sailboat Sales Co.