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

Brokerage Sailboats

Listings Updated 08/07/20

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
20 Pacific Seacraft Flicka 20 1979 Owl The world's most famous and well-traveled 20-foot cruising sailboat, the Flicka has sailed every ocean and circumnavigated the globe. A full-keel design drawn by Bruce Bingham, she offers four berths and standing headroom in a stout, sea-kindly package. Built to exacting standards by Pacific Seacraft, she will take you any place you wish to sail. 18,000
23 Beneteau First 235 1988 OFOB Always fresh water sailed, two-owner, 1988 Beneteau 235 includes like new Honda 9.9 electric start outboard tuned summer 2019; new North mainsail with new Dutchman flaking system and furling genoa - all new August 2019. Marine head with holding tank. Harken roller furling; highway trailer in road ready condition. Decks, topsides and bottom all in excellent condition. Always fresh water sailed; Beneteau 235 is a big little boat. New to market May 2020. Currently in indoor heated storage at Crowley's Yacht Yard. 15,000
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. 5,000
25 W.D. Schock Harbor 25 2012 Sally Forth Mastervolt inboard electric with folding prop. Tiller steering with newer tiller pilot. Raymarine depth sounder, knotmeter, trip log mounted on cockpit bulkhead. Newer chart plotter. Doyle Leisure Furl in-boom furling mainsail. Hoyt furling self-tacking jib system. Lewmar winches. Jabsco marine head. Custom Pacific galvanized tandem-axle trailer. SOLD
27 Hunter 27 1991 Rum Reach This 2-owner, always fresh-water sailed boat is fun, roomy, and easy to sail. It has a 9hp Yanmar. Sail inventory includes a main, 2012 Doyle Quicksilver 2 genoa, and a jib. SOLD
28 Cal 28 1988 Seventh Heaven Well maintained, always Lake Michigan sailed boat. Yanmar 18hp diesel. Wheel steering. 18,000
30 Beneteau 305 1987 Sweet Isolation Popular Beneteau 305. One owner boat, always Lake Michigan sailed. Features a Volvo diesel, autopilot, tiller steering, Schaefer roller furling, newer sails, and Tides Marine Mainsail Track, and Doyle Stackpack. 16,500
32 Beneteau 321 1995 Solace 3-owner, fresh water sailed, comfortable cruising sailboat, well-maintained. In mast-furling mainsail. furling genoa, autopilot, Aft cabin version with one large private roomy aft-cabin, and a private cabin forward. 42,000
32 O'Day 322 1987 Recess Comfortable and roomy boat has cruised the Great Lakes since new. Never in salt water. All new Doyle sails in 2010 including main, furling genoa (reconditioned in 2018 with new sunshield) and Doyle APC Cruising Spinnaker with ATN Sleeve (not used since 2013). 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. Stored winters outdoors, but wrapped. The boat is ready to go and was just washed and polished. Recess has also been in family/friends hands since day one so certainly cared for from owner to owner. SOLD
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. 48,000
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 Catalina 34 1989 Accomplished Well maintained, Lake Michigan sailed boat. Shrink-wrapped over winters. 4' draft.
July 2019 marine survey
34 Hunter 34 1983 Dream Catcher Always fresh water sailed. Current owner has owned, and professionally maintained the boat at Crowley's Yacht Yard since 1997. 15,500
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. 135,000
35 Beneteau 35s5 1989 Yukon Super clean. Powered by 2007 Perkins diesel with approximately 300 hours. Beneteau supplied rudder new in 2014 with 8 barrier coats. SOLD
35 Beneteau Oceanis 352 1998 Funny Farm Always professionally maintained by Crowley's Yacht Yard. Only two owners since new. Deck and hull have been washed, buffed and waxed annually. Exterior teak refinished in September 2019. Bottom painted annually with VC-17. Always fresh water sailed. SOLD
36 Beneteau First 36.7 2006 Lazy Lightning Low hours. Excellent condition. 99,000
36 Catalina 36 1983 Sailavie Tall mast. Roller furling genoa. All lines lead to cockpit for easy handling. Autohelm 3000. 12-ft. wide beam allows ample room in salon with amazing 6' 5" headroom. Dodger and bimini. Ready to sail. 34,500
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 Hunter Legend 37.5 1989 Kaleidoscope Well cared for boat sailed exclusively in Lake Michigan. Long list of upgrades in the last 2 years including A/C and Heat in all cabins, new electronics, new dodger and bimini, new spring mattress in the spacious aft cabin, and much more. SOLD
38 Finnyacht Finn 381 1987 Blessings Designed by Elvind Finn and built by Still Yachts to high Finnish yacht building standards. Very fast and well behaved. Stored indoors heated over winters. Fresh water only, except her first year was in salt water. SOLD
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. 20,000
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. 65,000
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

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