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

Brokerage Sailboats

Listings Updated 01/16/18

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
21 Open Sailing - Pogo 2 2011 812 21' Mini 6.50m class racer. Has been used for daysailing only; never raced. Well equipped standing and running rigging. Fin keel with bulb & twin rudders. NKE autopilot. Six sails. Honda 5hp outboard motor. Custom dual-axle trailer. Well maintained, no damage ever, and upgraded electronics. Currently stored indoor heated at Crowley's Yacht Yard in Chicago. 39,000 UA
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
26 Colgate 26 1998 Poco Veliero 2 owner boat. Always fresh water sailed. Well maintained. Furling genoa, conventional hoist main, nylon spinnaker. Large cockpit. Tiller steering. Mercury 6hp 4-stroke outboard motor. Draft is 4' 6". Ablative anti-fouling applied June 2017. Bottom has been sanded and painted every year. Never any sign of osmotic blistering. Boat has been in fresh water since 2002. Topsides were cleaned, deoxidized and waxed in June 2017 18,000
26 MacGregor 2001 LeRoi Trailer, outboard motor, call for details. SOLD
27 Catalina 1986 Out & About Diesel, wheel, roller furling are a few of the features of this well-kept Catalina 27. Standing headroom, ready to go! Nice interior and cockpit cushions. SOLD
27 Hunter 27 2005 Trade Winds Nicely equipped 2-owner boat has sailed only in fresh water; Lake Carlyle and Lake Michigan. Boat has been well-maintained and is in very good condition. The 16 hp Yanmar diesel has only 186 original hours. The sails are currently being cleaned at UK Sail Makers in Chicago and will be available to see. UK has stored and maintained the sails over winters.
July 2013 marine survey
28 Sabre 1978 Island Sunset Lake Michigan cruised, well maintained classic Sabre 28. Sturdy boat, diesel engine, roller furling, wheel steering with autopilot. VC-17 bottom, painted teak trim. Annual maintenance by Crowley's Yacht Yard. Good sail inventory. Easy to sail single-handed. SOLD
30 Irwin 1976 Grandyear Excellent choice for the casual day-sailor on a budget, this is a good old boat that has been faithfully maintained. Roomy cockpit, wide walkways, and ample interior volume. New sails in 2013. 8,900
30 Pearson 303 1986 Red Well maintained 3-owner Lake Michigan cruised boat. Wheel steering, Raymarine autopilot and wind/depth/speed. UK Main (2007), UK furling genoa (2007) and UK spinnaker (2007). Sleeps 5 in 4 berths. Private forward cabin with double vee-berth. Enclosed head. Main cabin with opposing setted berths, drop-down dining table, galley and nav station, open quarter-berth. Draft is 4' 4". Yanmar 18hp diesel. 28,000
32 Hunter 320 2001 Irish Ayes Very lighly used. Professionally serviced and maintained by Crowley's Yacht Yard. Furling main and genoa; and autopilot make single-handed sailing a breeze. Always sailed in Lake Michigan in the Chicago area. Very clean and in fine condition. Newer Raymarine instruments. Smooth bottom painted spring 2016 with Pettit Hydrocoat. SOLD
32 O'Day 32cc 1977 Kettle Ann Center cockpit. Two separate cabins. Regularly maintained. In-mast Roller Furling Mainsail. Dinghy davits. Canvas cockpit enclosure. Sails recently repaired, New halyards in 2013. New fuel tank in 2012. New winter cover in 2013. LED lighting throughout (new in 2016). New 2016 Garmin GPS Chartplotter with North America chip. Boat is loop ready! Completed the loop in August 2017. Very economical and comfortable way to do the loop.
Read a August 2017 article about Kettle Ann.
33 Beneteau 2005 September Song One owner boat, always fresh water sailed. Well maintained, clean boat. Autopilot, furling main and genoa. 69,900
33 Endeavour 33 1985 Mrs. Darling Beautiful teak interior. Autopilot and GPS. Yanmar diesel. A well maintained, well built sailing yacht maintained by a professional. Nice boat!
Marine Survey
33 Hunter 2011 Inner Peace One-owner, always fresh water sailed on Lake Michigan. Very well maintained; oil changed at the beginning, middle, and end of every season. New UK mainsail in 2016. Central air conditioning and heat. Electric flush head. Lewmar folding wheel. Yanmar 29hp diesel engine. Raymarine ST-60 depth and speed. Refrigerator and freezer. 105,000
33 Tartan T-10 1984 Druid Professionally maintained by Crowley's Yacht Yard. New Awlgrip topsides in 2014. VC-17 bottom. Sleeps 6. Teak & holly cabin sole; porta potti head; Datamarine instruments; Garmin GPS; Steel storage cradle; spinnaker gear; Lewmar winches. 9 sails included. Dutchman mainsail control system. 15,000
34 Beneteau 343 2005 At Last In-mast furling mainsail. Always fresh water. Very conscientious and maintenance-focused owners used her for daysailing, long and short range cruising on Lake Michigan. All systems in working condition. Regularly stored shrink-wrapped in off season. Built in South Carolina, USA. July 2017: Deck and topsides washed, buffed and waxed. Interior cleaned and detailed. Cockpit/anchor lockers washed. Exterior teak surfaces cleaned and new Sikkens/Cetol applied.
Oct. 2014 Marine Survey
34 C&C 34 1982 Marinochka Major restoration on this well-equipped, racer/cruiser. Complete new Awlgrip job in 2014; hull, deck and non-skid prepped, primed and painted, deck hardware re-bedded. Smooth VC17 bottom painted annually. Yanmar diesel engine. New transmission in 2014. Wheel steering, autopilot, Harken roller furling. All new electronics in 2015. New rudder in 2016. Always in fresh water, Lake Michigan. Reupholstered cushions, new windows, new folding prop. Beautiful teak-and-holly sole. SOLD
34 Peterson 34 1980 Odyssey always sailed off the Chicago lakefront. In 2007 her decks were stripped, prepped and painted, both non-skid and smooth, and topsides/transom as well - all in sprayed Awlgrip. 19,000
35 C&C 35 MK III 1985 Mr. JJ Updated electronics, sails, winches, etc. New VC-17 sprayed bottom June 2016. The C&C 35 MK III offers exceptional cruising and racing performance. She has the speed to win on the race course and the comfort for extended cruising. The mechanical systems, running rigging and bottom/keel/rudder are up to date and have always been very well maintained.
Sailing Magazine
Designer's Comments
35 J Boats J/35 1984 Bretwalda Always fresh water raced/cruised on the Great Lakes. New sails in 2016. 18,000
35 Tartan Thomas 35 1989 Coyote fast, comfortable racer/cruiser. Masthead rig. Always professionally yard maintained and serviced; constantly upgraded.
Sailing World Article and Original Thomas 35 Brochure
36 Catalina 36 MKII 1999 Morning Star V Always fresh water. Cruised on Lake Michigan by one-owner since new. Stored outdoors shrink-wrapped every winter, and serviced/winterized annually by Crowley's Yacht Yard. Raymarine autopilot and instruments. All new blue canvas in 2013 including dodger, bimini, sailcover, center cover, and binnacle cover. Central air-conditioning and heat. 79,000
36 Dufour 2007 Lily Features stylish modern lines and beautiful teak decks. Laid out for efficient sail handling or single-handed sailing. Shoal keel with 5' 7" draft. Removable bimini and dodger. 109,000
36 C&C 36 1979 Weatherly Clean and properly maintained racer/cruiser. Fully equipped for short handed sailing, or a full crew. Sails are all in good condition. Easy to sail and ready to go. 21,000
36 Sabre 1986 Shannara Always fresh water sailed boat. Meticulously maintained and continuously upgraded. Exterior fiberglass is original gelcoat in excellent condition. All exterior teak was sanded bare and covered with Cetol in 2009. Interior teak and cabin sole are beautifully finished with hand rubbed varnish. This boat has lots of usable storage space for long-term voyaging. Newer Raymarine electronics. Shrink-wrapped annually over winters. Annual bottom paint. Engine regularly maintained.
Marine Survey from 2014
36 Sabre Custom 1987 Probe Well maintained custom one-off racer cruiser. Comfortable cruising interior. 6' 2" headroom. Wheel steering.
Marine Survey
Builder's Notes
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. 48,000
37 Irwin 1972 Jung Frau Always fresh water sailed on Lake Michigan. Winterized annually, new bottom paint annually. New mainsail and jib in 2016.
Rig Inspection Report
37 Tartan 37 centerboard 1977 Zephyr Beautiful Tartan 37 with centerboard keel. Custom teak interior with genuine teak and holly sole. Five oversize self-tailing winches, Lofran anchor windlass, radar, B&G Pilot. Fresh water only. Professional annual maintenance. Stored winters indoors/heated at Crowley's Yacht Yard in Chicago. Summers at Belmont harbor in Chicago. Sparkman & Stephens design.
June 2017 Marine Survey
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. 75,000
43 Beneteau 423 2007 Gyp-Sea Very clean, very beautiful, very well kept. Only one owner since new, always sailed in Lake Michigan. Two-cabin layout. Factory equipment includes VC17 bottom, ST60002+ Linear Type 2 Autopilot, Raymarine E80 Multifunction Nav D, Raystar 125 LP WAAS, satellite receiver, hatch screens, upgraded cushion fabric, gennaker gear, upgraded winches, electric flush toilet, electrical inverter. 162,000

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