Sailboat Sales Co. - Brokerage Sailboats


Sailboat Sales Co - 3434 E. 95th St - Chicago Illinois 60617 - Phone 773.221.8880 - Fax 773.221.8881

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Brokerage Sailboats

Listings Updated 02/4/10

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
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LOA Type Year Name Remarks Price
27 Catalina 27 1980 Ojibwa Many upgrades since 2000: Engine overhaul, newer sails, Vertglas polycoat, newer knot/log, newer cockpit cushions, all through deck fittings rebedded, teak refinished spring '09, new Furlex roller furling in '08, new throttle, gearshift, and motor controller in '09, new batteries in '08. This is a standard rig with traditional interior. 14,900
27 Catalina 27 SD 1985 Retreat Shallow draft Scheel keel, upgraded Barient self-tailing primary winches, Autohelm autopilot and navigation instruments, diesel engine, roller furling, North Sails are just the hightlights of this always freshwater-sailed Catalina 27. Stored indoors. 14,000
28 Hunter 280 1996 Impulse Sloop rig, shoal draft keel, spade rudder, keel stepped mast. Wheel steering. Interior features double vee-berth forward, double aft berth, enclosed head, galley, and dinette. Headroom is 6' 1". 31,000
28 Hunter 280 1998 Carpé Diem NEW PRICE. Very well kept 1998 Hunter 280 in Chicago. Wing keel; autopilot; GPS; Dutchman sail flaking system; solid vang; furling genoa; full bimini. 30,000
28 O'Day 28 1979 Somewhere in Time Wheel steering, Yanmar diesel, Autopilot, roller furling, 4 sails and gennaker, galley with stove and refrigerator, and enclosed marine head. 14,000
28 Sabre 28 1974 Laura Pearl Well maintained boat. New roller furling in '03. Wood refinished in '04. New refrigeration in '98. New cockpit cushions in '08. 9,000
29 Beneteau First 29 1985 KAOS Fast, fun, family boat in very good overall condition. Gorgeous all-teak interior. Tiller steering with auto helm, shore power, roller furling. This boat has been daysailed with light cruising on Lake Michigan. 26,000
29 Beneteau First 29 1985 Liberte Always a Lake Michigan boat, only 2 owners. Overall condition is good. Engine and transmission are serviced yearly. Tiller steering. New batteries, sails, and running rigging. SOLD
29 C&C 29 1977 Avatar New Raymarine instruments in 2004; North mainsail in 2001; and North Genoa in 2003. Brand-new VC-17 bottom (April 2009). 19,000
30 Melges 30 1996 Bluebird Fast, competitive sportboat racer stored indoors in Lake Geneva has been sailed exclusively on Lake Geneva. Inventory includes two keels; a 7' keel which came with the boat, and a 5.5' keel, which is currently on the boat. Also included is a highway trailer. 65,000
30 Morris Leigh 30 1981 Buckaroo Fine example of this popular double-ender. Hull no. 7, originally built by and for Tom Morris, this Leigh is well thought out and very well finished with a top notch pedigree. Located near Chicago, we are the Chicago-area cooperating brokerage for this yacht. 68,000
30 S2 9.2A 1981 Tamworthian Sturdy cruising sloop, always fresh water sailed in Lake Michigan. Only 2 owners. All lines lead to cockpit for easy handling. Roller furling genoa. Spacious interior. Swim ladder on transom. 19,000
31 CAL 31 1983 Eagle's Nest Classic boat with many good years ahead. Dutchman system on mainsail, roller furling genoa for easy daysailing. Swim ladder, large cockpit with beautiful folding teak table. Comfortable salon with very large galley area. Only two owners and always in Lake Michigan. 21,000
32 C&C 32 1981 Erendira A comfortable and forgiving cruiser, roomy above and below. Erendira is probably the best rigged C&C 32 on Lake Michigan. Wheel steering. Interior teak in excellent condition. Owner is very motivated to sell quickly, which is reflected in the low asking price. 26,000 UA
32 Ericson 32 1985 Briatar Diesel, wheel, Harken roller furling, hot & cold pressure water, bimini, two owner freshwater sailed boat. 22,000
32 Etap 32s 2003 La Otra Vida Winner of an innovation award for vertical steering system, tandem keel, and certified unsinkable. One-owner, always fresh water sailed in Lake Michigan. 99,800
32 Pearson 323 1979 Chelsea Capable cruiser in excellent condition. Always fresh water sailed. 29,500
32 Pearson 323 1980 Wind & Spirit Beautifully preserved and maintained example of a gracious cruising sailboat from the 1980s. Used for daysailing in Chicago and light cruising on Lake Michigan. All teak is smooth and shiny, the sails are washed and inspected annually, many systems have been updated. 30,000 UA
33 Hunter 33 2005 20-20 Foresight This lightly used, always Lake Michigan sailed boat is priced to sell fast. 80,000
34 Hunter 340 2000 Satori Clean, comfortable, and in excellent condition, with professionally installed central air conditioning system (2008), new mainsail (2008), and nearly new furling genoa. 79,900
34 Peterson 1980 Fun Factor Island Yachts Peterson 34 has been extensively restored by 2nd owner. Lots of upgrades since 2006. 29,650
34 Sabre 1983 Deo Gratias III 1983 Sabre 34 sailboat for sale in Chicago stored in a heated building at Crowley's Yacht Yard. 40,000
34 Tartan 34C 1976 TAR34389M76E Always Lake Michigan sailed Tartan 34C full keel with centerboard. Gleaming teak woodwork; sleeps 6; UK Mainsail new in '05; VC-17 bottom; Harken furling system; autopilot. 27,500
36 Beneteau 361 2002 Caribbean Dream Beautiful, always fresh water sailed boat. Furling main and genoa; Autohelm ST4000+; sleeps 7; private double aft cabin; private double forward cabin; head is aft with separate shower stall; comfortable salon with dining table that converts to double settee berth. 108,000
36 Carroll Marine / Tripp 36 1992 L.A. Woman Well maintained, 2-owner, always fresh water sailed racer-cruiser. 59,900
36 Catalina 36 1984 Vela Large solid fresh water boat, handles well, perfect for cruising and day sailing. All lines lead to cockpit for easy handling. Fully enclosed cockpit. Roomy salon with amazing headroom. Many extras. 45,000 UA
36 Catalina 36 TR 1989 Grace Newer full batten main and roller furling genoa. ST4000 autohelm. Well equipped, sleeps 8. Recent marine survey available. 59,500
36 Sydney 36 1998 Bounder Built in Australia by Bashford Boat Builders; includes 2003 custom 3-axle Triad trailer, performance epoxy bottom, carbon fiber mast, steel rod rigging, carbon fiber spinnaker pole, race sails. 89,000
38 Sydney 38 2000 Serenissima Price reduced for quick sale, but still excellent throughout, exclusively fresh water sailed/raced, great sail inventory. 149,000
39 Carroll Farr 395 2001 Zoom Highly sought after performance cruiser. Well-maintained, always freshwater-sailed perfect family cruiser with a varnished teak interior and comfortable amenities. Loaded with top notch gear & equipment, she is also ready for competitive racing. SOLD
40 Cheoy Lee Midshipman 40 1976 Ropes of Maui Natural teak decks, varnished teak cockpit, extensive use of teak on deck and below. Two large staterooms, each with private head and shower. Brand new diesel engine, other mechanicals, and fiberglass cabintops by Crowley's Yacht Yard Chicago. Electric windlass. Fresh water sailed in Lake Michigan since 1995. 48,000
40 O'Day 40 1986 Sugar Magnolia Spacious and comfortable cruising yacht with generous use of teak. Pressurized hot and cold water. Two private staterooms with ample light and ventilation. All lines and halyards trim to the cockpit for easy handling. Electric winch on the anchor. 60,000
40 O'Day 40 1987 True North Large and well-equipped cruising sailboat with heated main salon. Includes 2 staterooms, one forward one aft, each with private head and sink. Used for daysailing in Chicago as well as light cruising in Lake Michigan and the North Channel. Full complement of sails. Autopilot, radar, and electronics. Pressurized hot and cold water. 65,000
42 Beneteau First 42s7 1995 Margarite Fast performance racer-cruiser. Beautiful and comfortable interior with 2 private double cabins, two heads, large galley. Stock 42S7 with the addition of a power winch, microwave, custom mattress, Westerbeke generator, HVAC system, full ST6000 set with Autohelm, Radar, and GPS. SOLD
43 Hunter 430 Legend 1995 Barometer Sloup Newer radar, dodger & bimini, Autohelm autopilot, Harken roller furling, Yanmar diesel, and wheel steering. Interior amenities include two master staterooms, two heads, XM radio, and 6’ 6” headroom. 119,000
43 Wauquiez Centurion 41S 1996 Safari Offshore Class A boat, very safe with many redundant systems. Sailed in the Caribbean until 2003, then exclusively in Lake Michigan. Never raced. Can be single handed. 150,000

LOA	Type	Year	Name	Remarks	Price
27	Catalina 27	1980	Ojibwa	Many upgrades since 2000: Engine overhaul, newer sails, Vertglas polycoat, newer knot/log, newer cockpit cushions, all through deck fittings rebedded, teak refinished spring '09, new Furlex roller furling in '08, new throttle, gearshift, and motor controller in '09, new batteries in '08. This is a standard rig with traditional interior.	14,900
27	Catalina 27 SD	1985	Retreat	Shallow draft Scheel keel, upgraded Barient self-tailing primary winches, Autohelm autopilot and navigation instruments, diesel engine, roller furling, North Sails are just the hightlights of this always freshwater-sailed Catalina 27. Stored indoors.	14,000
28	Hunter 280	1996	Impulse	Sloop rig, shoal draft keel, spade rudder, keel stepped mast. Wheel steering. Interior features double vee-berth forward, double aft berth, enclosed head, galley, and dinette. Headroom is 6' 1".	31,000
28	Hunter 280	1998	Carpé Diem	NEW PRICE. Very well kept 1998 Hunter 280 in Chicago. Wing keel; autopilot; GPS; Dutchman sail flaking system; solid vang; furling genoa; full bimini.	30,000
28	O'Day 28	1979	Somewhere in Time	Wheel steering, Yanmar diesel, Autopilot, roller furling, 4 sails and gennaker, galley with stove and refrigerator, and enclosed marine head.	14,000
28	Sabre 28	1974	Laura Pearl	Well maintained boat. New roller furling in '03. Wood refinished in '04. New refrigeration in '98. New cockpit cushions in '08.	9,000
29	Beneteau First 29	1985	KAOS	Fast, fun, family boat in very good overall condition. Gorgeous all-teak interior. Tiller steering with auto helm, shore power, roller furling. This boat has been daysailed with light cruising on Lake Michigan.	26,000
29	Beneteau First 29	1985	Liberte	Always a Lake Michigan boat, only 2 owners. Overall condition is good. Engine and transmission are serviced yearly. Tiller steering. New batteries, sails, and running rigging.	SOLD
29	C&C 29	1977	Avatar	New Raymarine instruments in 2004; North mainsail in 2001; and North Genoa in 2003. Brand-new VC-17 bottom (April 2009).	19,000
30	Melges 30	1996	Bluebird	Fast, competitive sportboat racer stored indoors in Lake Geneva has been sailed exclusively on Lake Geneva. Inventory includes two keels; a 7' keel which came with the boat, and a 5.5' keel, which is currently on the boat. Also included is a highway trailer.	65,000
30	Morris Leigh 30	1981	Buckaroo	Fine example of this popular double-ender. Hull no. 7, originally built by and for Tom Morris, this Leigh is well thought out and very well finished with a top notch pedigree. Located near Chicago, we are the Chicago-area cooperating brokerage for this yacht.	68,000
30	S2 9.2A	1981	Tamworthian	Sturdy cruising sloop, always fresh water sailed in Lake Michigan. Only 2 owners. All lines lead to cockpit for easy handling. Roller furling genoa. Spacious interior. Swim ladder on transom.	19,000
31	CAL 31	1983	Eagle's Nest	Classic boat with many good years ahead. Dutchman system on mainsail, roller furling genoa for easy daysailing. Swim ladder, large cockpit with beautiful folding teak table. Comfortable salon with very large galley area. Only two owners and always in Lake Michigan.	21,000
32	C&C 32	1981	Erendira	A comfortable and forgiving cruiser, roomy above and below. Erendira is probably the best rigged C&C 32 on Lake Michigan. Wheel steering. Interior teak in excellent condition. Owner is very motivated to sell quickly, which is reflected in the low asking price.	26,000 UA
32	Ericson 32	1985	Briatar	Diesel, wheel, Harken roller furling, hot & cold pressure water, bimini, two owner freshwater sailed boat.	22,000
32	Etap 32s	2003	La Otra Vida	Winner of an innovation award for vertical steering system, tandem keel, and certified unsinkable. One-owner, always fresh water sailed in Lake Michigan.	99,800
32	Pearson 323	1979	Chelsea	Capable cruiser in excellent condition. Always fresh water sailed.	29,500
32	Pearson 323	1980	Wind & Spirit	Beautifully preserved and maintained example of a gracious cruising sailboat from the 1980s. Used for daysailing in Chicago and light cruising on Lake Michigan. All teak is smooth and shiny, the sails are washed and inspected annually, many systems have been updated.	30,000 UA
33	Hunter 33	2005	20-20 Foresight	This lightly used, always Lake Michigan sailed boat is priced to sell fast.	80,000
34	Hunter 340	2000	Satori	Clean, comfortable, and in excellent condition, with professionally installed central air conditioning system (2008), new mainsail (2008), and nearly new furling genoa.	79,900
34	Peterson	1980	Fun Factor	Island Yachts Peterson 34 has been extensively restored by 2nd owner. Lots of upgrades since 2006.	29,650
34	Sabre	1983	Deo Gratias III	1983 Sabre 34 sailboat for sale in Chicago stored in a heated building at Crowley's Yacht Yard.	40,000
34	Tartan 34C	1976	TAR34389M76E	Always Lake Michigan sailed Tartan 34C full keel with centerboard. Gleaming teak woodwork; sleeps 6; UK Mainsail new in '05; VC-17 bottom; Harken furling system; autopilot.	27,500
36	Beneteau 361	2002	Caribbean Dream	Beautiful, always fresh water sailed boat. Furling main and genoa; Autohelm ST4000+; sleeps 7; private double aft cabin; private double forward cabin; head is aft with separate shower stall; comfortable salon with dining table that converts to double settee berth.	108,000
36	Carroll Marine / Tripp 36	1992	L.A. Woman	Well maintained, 2-owner, always fresh water sailed racer-cruiser.	59,900
36	Catalina 36	1984	Vela	Large solid fresh water boat, handles well, perfect for cruising and day sailing. All lines lead to cockpit for easy handling. Fully enclosed cockpit. Roomy salon with amazing headroom. Many extras.	45,000 UA
36	Catalina 36 TR	1989	Grace	Newer full batten main and roller furling genoa. ST4000 autohelm. Well equipped, sleeps 8. Recent marine survey available.	59,500
36	Sydney 36	1998	Bounder	Built in Australia by Bashford Boat Builders; includes 2003 custom 3-axle Triad trailer, performance epoxy bottom, carbon fiber mast, steel rod rigging, carbon fiber spinnaker pole, race sails.	89,000
38	Sydney 38	2000	Serenissima	Price reduced for quick sale, but still excellent throughout, exclusively fresh water sailed/raced, great sail inventory.	149,000
39	Carroll Farr 395	2001	Zoom	Highly sought after performance cruiser. Well-maintained, always freshwater-sailed perfect family cruiser with a varnished teak interior and comfortable amenities. Loaded with top notch gear & equipment, she is also ready for competitive racing.	SOLD
40	Cheoy Lee Midshipman 40	1976	Ropes of Maui	Natural teak decks, varnished teak cockpit, extensive use of teak on deck and below. Two large staterooms, each with private head and shower. Brand new diesel engine, other mechanicals, and fiberglass cabintops by Crowley's Yacht Yard Chicago. Electric windlass. Fresh water sailed in Lake Michigan since 1995.	48,000
40	O'Day 40	1986	Sugar Magnolia	Spacious and comfortable cruising yacht with generous use of teak. Pressurized hot and cold water. Two private staterooms with ample light and ventilation. All lines and halyards trim to the cockpit for easy handling. Electric winch on the anchor.	60,000
40	O'Day 40	1987	True North	Large and well-equipped cruising sailboat with heated main salon. Includes 2 staterooms, one forward one aft, each with private head and sink. Used for daysailing in Chicago as well as light cruising in Lake Michigan and the North Channel. Full complement of sails. Autopilot, radar, and electronics. Pressurized hot and cold water.	65,000
42	Beneteau First 42s7	1995	Margarite	Fast performance racer-cruiser. Beautiful and comfortable interior with 2 private double cabins, two heads, large galley. Stock 42S7 with the addition of a power winch, microwave, custom mattress, Westerbeke generator, HVAC system, full ST6000 set with Autohelm, Radar, and GPS.	SOLD
43	Hunter 430 Legend	1995	Barometer Sloup	Newer radar, dodger & bimini, Autohelm autopilot, Harken roller furling, Yanmar diesel, and wheel steering. Interior amenities include two master staterooms, two heads, XM radio, and 6’ 6” headroom.	119,000
43	Wauquiez Centurion 41S	1996	Safari	Offshore Class A boat, very safe with many redundant systems. Sailed in the Caribbean until 2003, then exclusively in Lake Michigan. Never raced. Can be single handed.	150,000

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