Sailboat Sales Co. - Brokerage Sailboats 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 Sailboats

Listings Updated 06/20/25

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.
= Price recently reduced.
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 Picture
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. 38,000
28 Shannon 28 1981 Druid This beautiful Shannon 28 has spent her life in freshwater. Since 2017 Druid has been a 6-pack charter in Chicago. She has general yearly maintenance on filters, oil, impellers. 60,000
30 Catalina 30TR 1986 Stormy Stormy is an always fresh water 1986 Catalina 30 tall right and fin keel. Updated 150% genoa and harken roller furling. She has stak pack and lazy jacks. Bulkhead mount table layout. The owner has purchased his next boat so seriously for sale! 18,000
31 Tartan 3100 1995 Komokwa Tartan's reputation for solid construction and good workmanship apparent in this well-maintained boat. As with most Tartan designs, the quality and finish of the 3100 is a cut above other of it's size and design from the period. Beautiful teak bulkheads, furniture, nav station, cabinets, toe rail and grab rails. Nice balance between performance sailing and cruising comfort. 48,000
32 Catalina 320 1994 Canuck This beautiful 1994 C320 has been used for weekend daysailing on Lake Michigan. Canuck comes with a steel cradle and custom Garhauer dinghy davits with solar. She has had 2 owners and has had regular service intervals. SOLD

34 Hunter 34 1983 Dream Catcher Dream Catcher has always been a Chicago lakefront day sailed boat. Good bottom and keel-hull joint; rudder and decks, main bulkhead and compression post all seem solid, good opportunity for a DIY’er who wants a popular 34 footer with good bones at affordable price. 11,000
34 Elan Impression 34 2007 Flying Cloud Flying Cloud has always been a freshwater boat sailed on Lake Michigan. She has had excellent overall maintenance, and has lived indoors in a heated building during the winter months. 75,000
36 Hunter 36 2005 Serenity II Serenity II has been very well cared for and spent her life in freshwater. She has a salon area with two spacious cabins, head & shower and an excellent amount of storage space. *Available after July 31st 2025.* 83,000

37 Jeanneau Sun Odyssey 37 2000 Creola II Creola II is a fresh water, gently used example of the popular Jeanneau Sun Odyssey 37. She is turn-key ready for her next owner. Current owners have had the vessel since 2005 and she has been stored shrink-wrapped in St. Joe MI over winters and had all annual maintenance and winterizations performed. Creolat features a fully battened mainsail with Dutchman, so you can experience all she has to offer without the performance compromise of the under-canvased in-mast furling models. Standard deep draft performance keel. An easy and fun boat for racing or double-handed cruising. Also features newer 135% Genoa and a .75 oz cruising spinnaker! SOLD

36 Catalina 36 1994 Anne Ellen Anne Ellen has been used for Great Lakes cruising. This Catalina is in above average condition with many upgraded items! She comes with a 4 pad steel cradle. 62,000

36 Catalina 36 1990 Dreamcatcher Dreamcatcher has spent her entire life in freshwater. She is great for races or cruising and is easily handled by 2 people. Standard fin keel model with step-thru transom; new bottom paint October 2024 49,000

36 Beneteau First 36s7 1996 Reckoning Reckoning has had a very caring owner for the past 18 years. The engine has been serviced and winterized every year by CYY, along with a spring inspection done every year before hitting the water. Batteries are new (2024). This boat is equipped with modern electronics. Below deck is very slick and clean. The galley offers a stainless steel gimble oven with a 2-burner stove. It also includes a newer Isotherm fridge and freezer. The teak and cabin sole are in excellent condition. 60,000
37 Jeanneau Sun Odyssey 37 2005 Minerva's Dream Minerva's Dream has always been a freshwater boat and calls Lake Michigan home! This Sun Odyssey 37 has been meticulously taken care of the last 5 years. She has spent the last 5 years on the water in Chicago during the summer, and lives at Crowley's Yacht Yard during the winter. SOLD
37 Hunter Legend 37.5 1989 St. Anna This Hunter Legend has been used in Hammond Indiana for day sailing on Lake Michigan. She has had excellent overall maintenance. The decks are nonskid and have been repainted. St. Anna also had a new rudder (2022). 49,000

38 Wauquiez 38 MKI 1983 Innisfree Ted Hood keel-centerboard design, Innisfree has only ever seen always fresh water; brand new sails, rebuilt engine and new transmission. Some say Wauquiez is the French Swan. 30,000

40 Jeanneau Sun Odyssey 40.3 2007 Cherish the Day Cherish The Day has always been a freshwater, day sailed boat! She has been used as a time share with weekly maintenance. Lake Michigan is her home in the summer, and an indoor heated building has been her home in the winters. 119,000
40 Jeanneau Sun Odyssey 40.3 2007 Le Bateau Le Bateau is a proud veteran of the widely acclaimed Pinnacle sharing program during which time she was cleaned, detailed, and inspected weekly; spent every winter of her life from 2006-2021 in heated storage and it shows! In the late summer 2024 her teak cockpit inlays were professionally stripped, prepped, and received 3 coatings of Starbright. She is ready for a Used Boat Boatshow! SOLD
40 Beneteau Oceanis 40 2012 Superstition This Beneteau 40 has always been used for daysailing in Lake Michigan and is a great cruiser. Superstition has a brand new (2024) North Sails mainsail along with a like new Doyle APC gennaker. The Genoa halyard and all batteries were replaced in 2022/2023. She spends her off-season on an 8-post cradle and has been winterized by Crowley's Yacht Yard including the engine, water and holding tanks, and batteries. 155,000
43 Alden Schooner 309 1929 Allegro Allegro is a 1929 John Alden schooner built by Goudy & Stevens. She is located in Chicago USA. Allegro spends her winters in a heat controlled building and summer on a mooring ball in Monroe Street Harbor. For the last 33 years Allegro has been lovingly maintained by the owner and professionally restored by expert shipwrights including Wayne Shibley of Chicago. 175,000

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.	38,000
28	Shannon 28	1981	Druid	This beautiful Shannon 28 has spent her life in freshwater. Since 2017 Druid has been a 6-pack charter in Chicago. She has general yearly maintenance on filters, oil, impellers.	60,000
30	Catalina 30TR	1986	Stormy	Stormy is an always fresh water 1986 Catalina 30 tall right and fin keel. Updated 150% genoa and harken roller furling. She has stak pack and lazy jacks. Bulkhead mount table layout. The owner has purchased his next boat so seriously for sale!	18,000
31	Tartan 3100	1995	Komokwa	Tartan's reputation for solid construction and good workmanship apparent in this well-maintained boat. As with most Tartan designs, the quality and finish of the 3100 is a cut above other of it's size and design from the period. Beautiful teak bulkheads, furniture, nav station, cabinets, toe rail and grab rails. Nice balance between performance sailing and cruising comfort.	48,000
32	Catalina 320	1994	Canuck	This beautiful 1994 C320 has been used for weekend daysailing on Lake Michigan. Canuck comes with a steel cradle and custom Garhauer dinghy davits with solar. She has had 2 owners and has had regular service intervals.	SOLD
34	Hunter 34	1983	Dream Catcher	Dream Catcher has always been a Chicago lakefront day sailed boat. Good bottom and keel-hull joint; rudder and decks, main bulkhead and compression post all seem solid, good opportunity for a DIY’er who wants a popular 34 footer with good bones at affordable price.	11,000
34	Elan Impression 34	2007	Flying Cloud	Flying Cloud has always been a freshwater boat sailed on Lake Michigan. She has had excellent overall maintenance, and has lived indoors in a heated building during the winter months.	75,000
36	Hunter 36	2005	Serenity II	Serenity II has been very well cared for and spent her life in freshwater. She has a salon area with two spacious cabins, head & shower and an excellent amount of storage space. Available after July 31st 2025.	83,000
37	Jeanneau Sun Odyssey 37	2000	Creola II	Creola II is a fresh water, gently used example of the popular Jeanneau Sun Odyssey 37. She is turn-key ready for her next owner. Current owners have had the vessel since 2005 and she has been stored shrink-wrapped in St. Joe MI over winters and had all annual maintenance and winterizations performed. Creolat features a fully battened mainsail with Dutchman, so you can experience all she has to offer without the performance compromise of the under-canvased in-mast furling models. Standard deep draft performance keel. An easy and fun boat for racing or double-handed cruising. Also features newer 135% Genoa and a .75 oz cruising spinnaker!	SOLD
36	Catalina 36	1994	Anne Ellen	Anne Ellen has been used for Great Lakes cruising. This Catalina is in above average condition with many upgraded items! She comes with a 4 pad steel cradle.	62,000
36	Catalina 36	1990	Dreamcatcher	Dreamcatcher has spent her entire life in freshwater. She is great for races or cruising and is easily handled by 2 people. Standard fin keel model with step-thru transom; new bottom paint October 2024	49,000
36	Beneteau First 36s7	1996	Reckoning	Reckoning has had a very caring owner for the past 18 years. The engine has been serviced and winterized every year by CYY, along with a spring inspection done every year before hitting the water. Batteries are new (2024). This boat is equipped with modern electronics. Below deck is very slick and clean. The galley offers a stainless steel gimble oven with a 2-burner stove. It also includes a newer Isotherm fridge and freezer. The teak and cabin sole are in excellent condition.	60,000
37	Jeanneau Sun Odyssey 37	2005	Minerva's Dream	Minerva's Dream has always been a freshwater boat and calls Lake Michigan home! This Sun Odyssey 37 has been meticulously taken care of the last 5 years. She has spent the last 5 years on the water in Chicago during the summer, and lives at Crowley's Yacht Yard during the winter.	SOLD
37	Hunter Legend 37.5	1989	St. Anna	This Hunter Legend has been used in Hammond Indiana for day sailing on Lake Michigan. She has had excellent overall maintenance. The decks are nonskid and have been repainted. St. Anna also had a new rudder (2022).	49,000
38	Wauquiez 38 MKI	1983	Innisfree	Ted Hood keel-centerboard design, Innisfree has only ever seen always fresh water; brand new sails, rebuilt engine and new transmission. Some say Wauquiez is the French Swan.	30,000
40	Jeanneau Sun Odyssey 40.3	2007	Cherish the Day	Cherish The Day has always been a freshwater, day sailed boat! She has been used as a time share with weekly maintenance. Lake Michigan is her home in the summer, and an indoor heated building has been her home in the winters.	119,000
40	Jeanneau Sun Odyssey 40.3	2007	Le Bateau	Le Bateau is a proud veteran of the widely acclaimed Pinnacle sharing program during which time she was cleaned, detailed, and inspected weekly; spent every winter of her life from 2006-2021 in heated storage and it shows! In the late summer 2024 her teak cockpit inlays were professionally stripped, prepped, and received 3 coatings of Starbright. She is ready for a Used Boat Boatshow!	SOLD
40	Beneteau Oceanis 40	2012	Superstition	This Beneteau 40 has always been used for daysailing in Lake Michigan and is a great cruiser. Superstition has a brand new (2024) North Sails mainsail along with a like new Doyle APC gennaker. The Genoa halyard and all batteries were replaced in 2022/2023. She spends her off-season on an 8-post cradle and has been winterized by Crowley's Yacht Yard including the engine, water and holding tanks, and batteries.	155,000
43	Alden Schooner 309	1929	Allegro	Allegro is a 1929 John Alden schooner built by Goudy & Stevens. She is located in Chicago USA. Allegro spends her winters in a heat controlled building and summer on a mooring ball in Monroe Street Harbor. For the last 33 years Allegro has been lovingly maintained by the owner and professionally restored by expert shipwrights including Wayne Shibley of Chicago.	175,000

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