Sailboat Sales Co. - Brokerage Powerboats for sale in Chicago


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

HOME BROKERAGE SAILBOATS BROKERAGE POWERBOATS OUR STORY FOR BUYERS FOR SELLERS F.A.Q. LINKS CROWLEY'S

Brokerage Powerboats

Listings Updated 05/03/25

Sailboat Sales Co. at Crowley's Yacht Yard in Chicago an excellent selection of used powerboats 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 photo gallery and full specs.
= 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.

Length Make Year Boat Name Remarks Price
27 Chris-Craft Commander 1967 Bella True to her namesake, Bella is a bespoke head turner. Set up for entertaining, with an open layout and plenty of room for guests, this Chris-Craft has been custom built as a one-of-a-kind picnic boat. Custom cockpit layout and upholstery. Newly refinished teak flooring and brightwork. Superb topsides finished in Awlgrip Flag Blue with white/red boot stripe. The bottom has been soda blasted and finished with seven barrier coats and Petit white anti-fouling paint in 2020. Oversize teak swim platform. Strong running 454 and velvet drive. There is no other Commander like it - prepare to be noticed! 35,000
28 Wellcraft Martinique 2800 2002 Chase N Hope The Martinique is a luxurious cruiser with two 4.3L MerCruiser V6 engines. Chase N' Hope has been well maintained and his ready for her next owner. Below decks the galley includes a refrigerator, microwave, and electric range. 12,000 BTU Marine Air Conditioning unit, electric Vacuflush head, pressure water and hot water heater included. SOLD
28 Carolina Classic 2000 Meltdown Twin Volvo Penta diesels, 240hp each. One owner since new. Always fresh water, Lake Michigan boat. Very well maintained. Trailer is included. Owner has kept Meltdown in inside heated storage since new in 2000; pride of ownership is apparent from first glance; diesels have 1350 hrs and have been maintained by certified marine diesel mechanics per manufacturer specs at every hour point. SOLD
29 Dyer 29 Trunk Cabin 1986 Goose A classic Downeast cruiser with timeless lines and legendary pedigree, Goose is a fine example of the highly regarded Dyer 29 Trunk Cabin. Built in 1986 by The Anchorage Inc. of Warren, RI, this boat represents decades of craftsmanship and performance on the water. With her solid fiberglass hull, classic sheer, and iconic trunk cabin profile, she’s equally at home on coastal waters or the Great Lakes. 79,000
29 Back Cove 2008 Jeunesse High-quality, single-diesel, straight-shaft, bowthruster-equipped boat with a comfortable performance. Hardtop. 315 hp Yanmar. Furuno radar and autopilot. SOLD
32 Monterey 322 Cruiser 2001 Wicked Game Well maintained, fresh water only Monterey 322. Wicked Game features twin Mercruiser 5.7L EFI engines, with only 350 hours. Most recent tune-up was 10 hours ago. She has been stored winters indoors heated. SOLD
35 Sea Ray 320 2005 Aquaholic Professionally maintained and winterized Searay 320 cruiser that has been on Lake Michigan the last 10 years. The head was serviced and rebuilt in 2021 with a Vacuflush. Aquaholic has 4 new 2023 batteries. Engine Hours: 719 - port & 319 - starboard. SOLD
40 Diesel Duck 2013 LuSeal This boat, designed by George Buehler and built of wood, has a displacement hull and is intended as a long distance, economical, live-aboard cruiser, capable of crossing oceans in relative comfort at a steady, slow, efficient speed. Hand crafted by Wayne Shibley Wooden Boats LLC, constructed of douglas fir wood with silicone bronze fasteners, everything is strong and heavy duty for serious cruising. Uses 1.5 gallons of fuel per hour on average at 6 to 7 knots. Two fuel tanks totaling 500 gallons. 129,000
41 Sea Ray 40 Sundancer 2007 Nauti is Nice Excellent condition. Fresh water only. Twin Cummins diesel engines. Central air conditioning and heat. Bow thruster. Onan generator. Two owner boat, cruised on Lake Michigan and Lake Guntersville. Stored in heated building over winters in Chicago. Currently in the water in Nashville, TN. SOLD

Length	Make	Year	Boat Name	Remarks	Price
27	Chris-Craft Commander	1967	Bella	True to her namesake, Bella is a bespoke head turner. Set up for entertaining, with an open layout and plenty of room for guests, this Chris-Craft has been custom built as a one-of-a-kind picnic boat. Custom cockpit layout and upholstery. Newly refinished teak flooring and brightwork. Superb topsides finished in Awlgrip Flag Blue with white/red boot stripe. The bottom has been soda blasted and finished with seven barrier coats and Petit white anti-fouling paint in 2020. Oversize teak swim platform. Strong running 454 and velvet drive. There is no other Commander like it - prepare to be noticed!	35,000
28	Wellcraft Martinique 2800	2002	Chase N Hope	The Martinique is a luxurious cruiser with two 4.3L MerCruiser V6 engines. Chase N' Hope has been well maintained and his ready for her next owner. Below decks the galley includes a refrigerator, microwave, and electric range. 12,000 BTU Marine Air Conditioning unit, electric Vacuflush head, pressure water and hot water heater included.	SOLD
28	Carolina Classic	2000	Meltdown	Twin Volvo Penta diesels, 240hp each. One owner since new. Always fresh water, Lake Michigan boat. Very well maintained. Trailer is included. Owner has kept Meltdown in inside heated storage since new in 2000; pride of ownership is apparent from first glance; diesels have 1350 hrs and have been maintained by certified marine diesel mechanics per manufacturer specs at every hour point.	SOLD
29	Dyer 29 Trunk Cabin	1986	Goose	A classic Downeast cruiser with timeless lines and legendary pedigree, Goose is a fine example of the highly regarded Dyer 29 Trunk Cabin. Built in 1986 by The Anchorage Inc. of Warren, RI, this boat represents decades of craftsmanship and performance on the water. With her solid fiberglass hull, classic sheer, and iconic trunk cabin profile, she’s equally at home on coastal waters or the Great Lakes.	79,000
29	Back Cove	2008	Jeunesse	High-quality, single-diesel, straight-shaft, bowthruster-equipped boat with a comfortable performance. Hardtop. 315 hp Yanmar. Furuno radar and autopilot.	SOLD
32	Monterey 322 Cruiser	2001	Wicked Game	Well maintained, fresh water only Monterey 322. Wicked Game features twin Mercruiser 5.7L EFI engines, with only 350 hours. Most recent tune-up was 10 hours ago. She has been stored winters indoors heated.	SOLD
35	Sea Ray 320	2005	Aquaholic	Professionally maintained and winterized Searay 320 cruiser that has been on Lake Michigan the last 10 years. The head was serviced and rebuilt in 2021 with a Vacuflush. Aquaholic has 4 new 2023 batteries. Engine Hours: 719 - port & 319 - starboard.	SOLD
40	Diesel Duck	2013	LuSeal	This boat, designed by George Buehler and built of wood, has a displacement hull and is intended as a long distance, economical, live-aboard cruiser, capable of crossing oceans in relative comfort at a steady, slow, efficient speed. Hand crafted by Wayne Shibley Wooden Boats LLC, constructed of douglas fir wood with silicone bronze fasteners, everything is strong and heavy duty for serious cruising. Uses 1.5 gallons of fuel per hour on average at 6 to 7 knots. Two fuel tanks totaling 500 gallons.	129,000
41	Sea Ray 40 Sundancer	2007	Nauti is Nice	Excellent condition. Fresh water only. Twin Cummins diesel engines. Central air conditioning and heat. Bow thruster. Onan generator. Two owner boat, cruised on Lake Michigan and Lake Guntersville. Stored in heated building over winters in Chicago. Currently in the water in Nashville, TN.	SOLD

HOME BROKERAGE SAILBOATS BROKERAGE POWERBOATS OUR STORY FOR BUYERS FOR SELLERS F.A.Q. LINKS CROWLEY'S