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

Brokerage Sailboats

Listings Updated 05/27/16

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
24 J Boats J/24 1985 Cats Paws Dry boat, clean, no soft spots. Sails in good condition. Outboard motor, dinghy, highway trailer. Must sell now! 4,999
25 Cal 25 MKII w/ trailer 1982 Instead Large cockpit, beamy cabin. Sleeps two in V-berth, two in salon, and one in starboard quarter-berth. Inboard diesel, roller furling, trailer. 4,500
27 Island Packet 1989 Endeavor Always fresh water sailed, well maintained boat. New 2014 standing rigging, lifelines, & electronics.
Original factory brochure
28 Hunter 280 1998 Carpe Diem Very well kept 1998 Hunter 280. Shoal draft, wing keel; autopilot; GPS; Dutchman sail flaking system; solid vang; furling genoa; full bimini; AM/FM/CD w/ 4 speakers & more. SOLD
29 Hunter 290 2000 M&Ms Very well cared for Hunter 290. Always daysailed on Lake Michigan. Standard 5' 4" fin keel offers excellent sailing performance. Yanmar diesel, wheel steering, autopilot, roller furling, 6' 2" interior headroom, cockpit dodger. Interior teak and bottom are in excellent condition. 35,500
30 Catalina 30 Tall Rig 1981 Nittany Rigged and ready to go sailing. A good old boat, only 2 owners since new and always on Lake Michigan. Current owner since 1983 has kept this boat in nice condition. Blue fabric upholstery is in very good condition. Rare teak-and-holly cabin sole. Stern perch seats, Lewmar winches, roller furling genoa, autopilot, full instrumentation. All lines lead aft for single-handed sailing. Atomic 4 inboard engine and drive train in perfect running condition. SOLD
30 Catalina 30 Tall Rig 1987 Lydia In-boom furling mainsail. Always fresh water sailed Tall Rig with Universal diesel engine. Only two owners since new. New sails in 2009. Autohelm autopilot, wheel steering, instruments and compass on binnacle. WinchRite motorised winch handle. CNG oven with 2-burner stove. New marine head. Custom canvas cover. 21,000
30 Irwin 30 1977 Freebird 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. Always in Lake Michigan, never in salt water. 7,000
30 Pearson 30 1976 Hannah This boat is clean, well maintained, and looks great. Deck looks clean, bright, and has none of the usual signs of age typical on most boats. Bottom looks clean and smooth and has a recent coat of bottom paint. All woodwork, interior and exterior has been well cared for. Winches, rigging, and electronics also upgraded recently. Decks are moisture free and always have been. 11,500
31 Bruce Roberts 310 1989 Innovation Built by hand, entirely from scratch, by a man and his son in Mogadore Ohio. All steel construction -- hull, deck, reinforced transom. Hull-to-deck joint is welded. Interior cabinetry is well crafted and finely fit. Large V-berth area and extra long quarter berth. The boat is in remarkable condition. Fin keel, spade rudder with reinforced skeg. Two anchors on the bow, third anchor on the stern. Self-tailing winches. Diesel engine.
Marine survey from 2004 is available to qualified buyers.
Read about Innovation in Great Lakes Sailor
31 Hunter 31 2006 A Wink and a Smile Always Lake Michigan sailed, one-owner Hunter 31. Sailed out of Hammond Marina. Features include in-mast furling mainsail; furling genoa; Selden rigid boom vang; stainless steel arch with mainsheet traveler and cockpit speakers; Lewmar folding steering wheel; walk-through transom. 6' 4" headroom in main cabin. SOLD
32 Beneteau Oceanis 321 1995 Latitudes In-mast roller furling mainsail, roller furling genoa. The Beneteau Oceanis 321 features cherry interior finish and spacious accommodations including aft cabin. Only 2 owners since new, it's a Lake Michigan boat, great for daysailing and cruising, easy to handle. Shallow draft just over 4 feet. The boat has never suffered major damage and has been excellently maintained.
Original factory line drawings
Original factory spec sheet
32 Sabre Tri-Cabin 1984 Vivace Fin keel, bright white beauty w/ tri-cabin interior. Always fresh water sailed. This is a great boat for a family and entertaining guests. The dinette and the cockpit easily fit 6 adults with room for food and beverages. Vivace take you anywhere you want to go in almost any weather. She tracks well and is a breeze to sail single handed.
Marine Survey
33 Endeavour 33 1985 Skidmarks Beautiful teak interior. Autopilot and GPS. Yanmar diesel. A well maintained, well built sailing yacht maintained by a professional. Nice boat!
Marine Survey
33 Flying Tiger 10M 2006 Solitary Solitary has been professionally rigged and maintained. She is a proven winner in both one design and PHRF racing. The boat has completed the Mac race (with the previous owner) and can easily be Mac ready. The boat is very fast, stable, and remarkably easy to sail. Solitary is a freshwater boat – she has been sailed primarily in Chicago and Lake Lanier, GA. The boat is easy to trailer and ramp launch. SOLD
33 SOCA Sailboats LS 10 2002 Sail La Vie Created by Sparkman and Stephens, the original concept of the T-Ten was to create a fun offshore boat with great sailing characteristics and weekend capabilities. What emerged was the first true offshore one design boat. The boat was an immediate success. More than 380 of these boats were delivered and most are still actively sailed and raced across the country. The New LS10 is the modern fruition of this highly successful design with an updated deck that incorporates a full cabinhouse designed to provide more headroom. A fully enclosed head, convenient galley and optional fold-away table enhance the comfortable space below for entertaining or cruising. 62,000
34 Beneteau First 345 1987 Mandalay Built in 1987, first launched in 1989, always in sweet waters of Lake Michigan. Current/second owners since ~ 1991. First owners used her very little; current owners primarily daysailing; very low engine hrs ... beautiful teak interior with some water damage at port side settee riser by cabin sole ... tall rig, Dutchman sail flaking system, roller furling genoa and cruising spinnaker. Built in South Carolina. Shrink-wrapped, mast up. SOLD
35 Bristol 35 1967 Talisman Well maintained and updated Bristol 35. Dinette table converts to double berth, total of 5 sleeping spaces. ST4000+ autopilot, GPS, new LED interior lighting, new VHF, new bluetooth stereo, new 2500 watt inverter, new microwave, new antifouling bottom and barrier coat, new water heater. SOLD
35 C&C 35 MK III 1985 Mr. JJ Updated electronics, sails, winches, etc. The C&C 35 MK III truly offers exceptional cruising and racing performance. She has the speed to win on the race course and offers the comfort for extended cruising. The mechanical systems and running rigging are up to date and have always been very well maintained. 44,500
35 Catalina 350 2006 Cara Mia CENTRAL AIR CONDITIONING AND HEATING! Spacious main salon with amazing headroom and generous use of teak throughout. Two private staterooms, head compartment with separate shower stall. In-mast furling mainsail, furling genoa. Huge storage areas. Only two owners; always fresh-water sailed; currently in Lake Lanier, Georgia, and previously in Lake Michigan. Very well equipped, turn-key condition, ready to go sailing. 115,000
35 Catalina 350 2004 Weekend Retreat Fresh water boat, heat, air-conditioning, dehumidifier, auto pilot, gps chartplotter, built-in coffee maker, two anchors- one with full chain rode, electric windlass, bimini and dodger, full cockpit cushions, cockpit vhs, flat screen tv, low hours, one owner. 109,900
36 K. Aage Nielsen Gumdrop Yawl Centerboard 1961 Magic Double-planked hull, mahogany over white cedar on white oak frames. Built by Paul E. Luke in East Boothbay, Maine. MAGIC is one of six sisters built to the Gumdrop design. She has been upgraded over the years as required and well cared for by very knowledgeable owners. Marine survey from 2010 is available. 39,000
36 C&C 110 2006 Time Away One owner boat. Carbon fiber mast and retracting bow sprit. Volvo diesel sail drive. Folding prop. 54" leather covered wheel. Raymarine GPS/Chartplotter. Autopilot. Interior is cherry wood and leather upholstery. 6' 4" headroom. Enclosed head with shower. Sleeps 6. Galley with 2-burner stove/oven, microwave, and refrigerated ice box. 139,000
36 Cape Dory 1982 Windslove One owner boat. Always Lake Michigan sailed. Perkins diesel engine. 29,000
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 Sabre 1985 Wave Dancer Always Lake Michigan sailed; well maintained; and in excellent condition. New UK Mainsail in 2011. New Raymarine autopilot in 2013. GPS and chartplotter; Harken roller furling; Westerbeke diesel; 40" Destroyer wheel.
Marine Survey
37 Hunter Legend 1989 Kaleidoscope Well cared for boat sailed in Lake Michigan by current owners since 1993. Wing keel 4' 9" draft. Sleeps 6. 6' 4" headroom. New fabric cushions in 2013. New refrigerator/freezer in 2014. Autohelm 4000+ (new in 2014). Garmin Chartplotter (new in 2010). Mainsail with cover and Dutchman (new in 2010). Marine Head (new in 2014). Main halyard winch is electric. SOLD
38 Baltic 38 DP 1983 Fastnet Doug Peterson (DP) used his racing experience to design this 1980’s hybrid cruiser/racer. She had outstanding performance and handling with a beautifully crafted yet spacious interior. She has a delightful after cabin, superb galley, and spacious saloon. The cockpit is designed for hard, crewed sailing. Like her sisters, she has stood the test of time well.
additional photos
YouTube video of sister ship
another YouTube video
39 Dufour 39 CC 1999 Sara Very well maintained center cockpit yacht used exclusively in Lake Michigan, except for the last 2 years on Florida's Gulf Coast. Only 3 owners and always lightly used for daysailing only. Air conditioning, heating, in-mast furling mainsail, large aft stateroom. Clean Boat a 9.5 out of 10.
2014 Marine Survey
40 C&C 40 1980 Incentive Sought-after racer/cruiser, very spacious teak interior, long berths, Yanmar diesel. Stretch-out room in every direction, all berths are at least 6' 6" long. Large galley. Light and airy with 3 opening deck hatches.
Marine Survey
C&C 40 - Still Turning Heads
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

All Rights Reserved, ©1996 - 2013 Sailboat Sales Co.