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

Brokerage Sailboats

Listings Updated 11/30/21

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
28 Cal 28 1988 Seventh Heaven Well maintained, always Lake Michigan sailed boat. Yanmar 18hp diesel. Wheel steering. 20,000
28 Sabre 28 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. Price includes complete winterizing, shrink wrapping, and full winter storage (including launch) at Crowley's Yacht Yard in Chicago through May 2022. SOLD
30 Catalina 30 MKII tall rig 1989 Wild Thyme Always fresh water sailed boat. Only three owners. 1st owner stored the boat indoors every winter. 2nd owner bought the boat in the fall of 2004 and stored the boat outdoors under a custom winter canvas cover every year. Third owner bought boat in 2014 and also stored boat under canvas cover over winters. Boat has been consistently well maintained in excellent condition. This boat is fun and easy to sail with the help of the Autohelm 4000 autopilot and Hood Seafurl roller furling. Sails are new in 2008. Central air conditioning was added in 1999. SOLD
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. SOLD
30 Catalina 30 TR 1983 Stormy Daniel's 1986 Catalina 30 TR listed November 2nd, 2021. Lake Michigan boat. 4 owners since new. Well maintained boat. 20,000
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 UA
32 Ericson 32-2 1975 Anodyne Current owner has maintained well. Extensive repairs and upgrades. Full interior/exterior re-upholstery (2018), new head holding system (2019), Deck and hull owner repainted. 1997 Yanmar diesel engine has been well maintained. Newer mainsail (2016), and genoa (2017). Multiple electronic upgrades. New rudder. Stored under cover in winter. 18,000
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. New bottom paint in 2020. New Garmin chartplotter in 2021. Many lines replaced in 2020/2021. SOLD
32 Pearson 323 1980 Wind & Spirit Gracious cruising sailboat from the 1980s. Used for day sailing in Chicago and light cruising on Lake Michigan. Volvo diesel. Wheel steering. Draft is 4' 5". 19,000
33 Canadian Sailcraft CS 33 1984 Punch Classic Canadian Sailcraft CS 33 in great condition. Recent upgrades in sails, instruments, cushions. Lake Michigan day-sailed boat. Current owner is 3rd owner. Professionally maintained. Stored indoors over winters. SOLD
33 Pearson Vanguard 1965 Grace A true classic sailboat - dark blue hull, Phil Rhodes designed with beautiful sheer line and gleaming teak brightwork. Grace is a head turner in every harbor. Current owners have lovingly maintained and improved her classic features. Grace under sail is very seakindly, tracking well with her full keel she can be both comfortable yet surprisingly exciting in a stiff 15 - 25 kt breeze. The current owners raised their family sailing and used her cozy cabin as a wonderful overnight respite every summer season over the last 20 years of ownership. Their hope is to find the next caring steward. This Vanguard features the popular dinette layout. Interior is painted white with teak accents and custom wood features. Since her launch, Grace has always been a freshwater boat sailing in Lake Michigan. She has primarily been a family cruising boat, but also lightly raced in by the second owner. The past 20 years she has been gently used as a day cruiser. SOLD
34 J Boats J/105 2001 Black Diamond Always fresh water sailed in Lake Michigan and Lake Huron. Current owner is 2nd owner. Stored outside shrinkwrapped over winters. 87,500
36 Beneteau First 36s7 1996 Reckoning Always sailed in Lake Michigan. Beautiful bright airy interior. Professionally maintained by Crowley's Yacht Yard for the last 18 years. Stored outdoors shrink-wrapped over winters. 55,000
36 S2 11.0 1982 Siren Song In the water and ready to sail. Currently moored in Belmont Harbor, Chicago. Two owner, fresh water, aft cockpit boat that has had excellent care. Full teak interior that features a large U-shaped galley, dinette, settee berth, custom enclosed quarter berth, navigation station, head and Vee berth forward. Teak and holly cabin sole, four opening ports, three overhead hatches, and two vents offer excellent ventilation, natural light and a feeling of spaciousness. The deck walk arounds are wide and have a raised bulwark for safety. Cradle included. SOLD
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 1982 Summer Home II Always fresh water sailed, two-owner, well maintained, lightly cruised Lake Michigan sailboat, custom winter cover. In-mast furling, bow thruster, central air-conditioning and heat. New mainsail and genoa in 2020. SOLD
37 Jeanneau Sun Odyssey 37 2004 Heartbreaker 2 cabin version. Newer air conditioning with reverse cycle heat. Autopilot. In-mast furling main, and furling genoa. Bimini. Shoal draft. SOLD
37 Jeanneau Sun Odyssey 37 2005 Mysterious Ways 2-cabin version. Mysterious Ways has been in a time share program since new. Always fresh water sailed in Chicago area. Very well and consistently maintained. Boat cleaned every week during the sailing season. Bilges and engine compartment cleaned at least annually. Stored indoors over winters in heated building at Crowley's Yacht Yard. SOLD
37 Shannon 37 Ketch 1987 Albatros Full keel centerboard. Ketch. Blue Awlgrip topsides. Diesel engine. Autopilot. In-mast furling main. Furling genoa. 84,000
38 Catalina 380 1999 School's Out Award winning design. Huge interior volume for entertaining. Tall rig; excellent sailing specs for lighter wind. Class A rating shows she will strong in a heavy wind. All fiberglass deck requires minimal maintenance. 1st 15 years in Lake Michigan; Charleston, SC for 4 years. Current owner brought her back to Lake Michigan for 2019 and 2020 seasons. Excellently maintained throughout. Located in Kenosha, Wisconsin. Please call for appointment.
April 2019 Marine Survey
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 Beneteau First 40.7 2002 Mojo Well maintained, always fresh water cruised and raced in Lake Michigan. 118,500

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