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

Brokerage Sailboats

Listings Updated 10/14/19

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. 5,000
25 Beneteau First 25 S 2013 Vagabundo One owner boat, very lightly used for weekend sailing since new in August 2014. Always fresh water sailed in the Chicago area. Regularly maintained by Crowley's Yacht Yard since new. Stored shrink-wrapped every winter. 49,900
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. 57,000
26 Morris Frances 26 1996 If Full keel double-ender designed by C.W. Paine, built by Morris Yachts of Maine. Was personal boat of Tom Morris. Offshore equipped, multiple sets of ground tackle, mechanical and electrical self-steering, Jordan series Drogue, 6 new sails, new dodger, custom Triad trailer, and two dinghies. Sailed mostly in Rhode Island Sound until 2003 then in Chicago from 2004. Stored indoors over winters.
July 2018 marine survey
27 Hunter 27 2005 In Search of You One-owner boat; sailed only in fresh water. Well-maintained and in excellent condition. Yanmar 16hp diesel with 127 hours. Wheel steering. In-mast furling main. 29,000
27 S2 Yachts 27 1985 Shiva One owner boat, always well maintained, always fresh water sailed. New mainsail in 2019. SOLD
29 Tanzer 1987 Voila Diesel engine, roller furling. New mainsail in 2019. Genoa new in 1998. Aft cabin with double berth. 7,500
30 Catalina 30 TR wing keel 1992 Winsome Wing keel, shallow draft. Used for day sailing and light cruising on Lake Michigan. Autopilot. VC-17 bottom. Updates include newer spinnaker and satellite radio. SOLD
30 J Boats J/30 1981 Breakaway Fast and fun racer-cruiser. Good sail inventory. Sleeps 6, and has 6' of interior headroom. Yanmar diesel engine. Very well cared-for boat. Always fresh water sailed. 2 owners. Current owner has owned boat since 1987. Topsides buffed and polished twice annually. VC17 bottom painted annually. New mainsail in 2017. Spinnaker is like new. 13,000
30 Sabre 30 MKIII 1988 Essence Beautifully kept and maintained Sabre 30. Always fresh water sailed. One owner since new. Always stored indoors heated over winters. Truly remarkable condition. SOLD
32 Sabre 1986 Bevo's Babe Always fresh water sailed. New Yanmar diesel engine in 2017. Raymarine ST60+ instruments. 5 sails. 33,000
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 336 1996 Duvetti Huge oval-shaped cockpit plus two perch seats on the stern railing make this boat the perfect platform for entertaining large groups of friends and family on the water. Below-decks features windows everywhere and 4 deck hatches for ample light and ventilation. Sleep 2 in the private forward cabin, 2 more in the aft cabin, plus the dining settee converts to another bed. Cook on the LP oven/stove, or on the portable gas grill at the transom. Air conditioning and heat. Shower. Innovative spreader arrangement eliminates the need for a backstay, creating easy access from the large swim platform. Mainsail, roller furling genoa, and 2 spinnakers. Wing keel with bulb allows access to shallower areas. Always a Lake Michigan boat, never in salt water.
November 2018 marine survey
Note: Survey issues have been addressed. See notes in Full Specs page of listing.
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 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 J Boats J/105 2000 Trinity Always fresh water sailed boat; in Lake Pepin and Lake Michigan. Only 2 owners since new in 2000. Very well maintained. 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.
Cruising World article about the Peterson 34
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. 63,000
36 Beneteau First 36.7 2006 Lazy Lightning Low hours. Excellent condition. 99,000
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. 39,000
37 Irwin Competition 37 1973 Geronimo The Irwin Competition 37 was one of the most successful performance cruising designs of the early-mid 1970s, regularly placing in the top positions in buoy and distance races in ports throughout the East and Gulf coasts and Great Lakes. Her generous cockpit, walkway and foredecks spaces combined with ultra-large volume interior spaces created a boat that was enjoyed by racing crews and cruising families alike. Geronimo has been owned by four Chicago area sailors, all of whom were serious, maintenance focused yachtsmen. 12,000
37 Jeanneau Sun Odyssey 37 2005 Spirit in the Night 2 cabin version. Bow thruster. Original sails. Furling main and genoa. Electric anchor windlass. Autopilot not operational. Boat has been in a time share program since new. Always fresh water sailed in Chicago area. 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. Beautiful boat! 79,000
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. 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

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