| LOA | Type | Year | Name | Remarks | Price | Picture |
| 20 | Chip Stulen Faering Design | 1987 | | 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 | |
| 25 | Maree Haute Django 7.70 | 2019 | | Single keel, double rudder version of the Django 7.70, from French builder Marée Haute. The boat is easily single or double-handed as all line are led aft to the coach roof. Electric Torqeedo engine. Sailed in Chicago since new. | | |
| 27 | Catalina 27 | 1983 | | Wun-Len has been well maintained and kept in good condition, with many upgrades. She has been used for day sailing and cruising on Lake Michigan. | 12,000 | |
| 28 | Pearson 28 | 1980 | | Island Time has seen very casual daysailing off the Chicago lakefront. A classic Bill Shaw design. She has a Universal 11hp diesel engine. The last 20 years she has recieved meticulous service. The decks were professionally checked and in great condition of fall 2023. | 11,000 | |
| 30 | Catalina 30TR | 1986 | | 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 | Beneteau First 305 | 1985 | | 1985 Beneteau First 305 designed by Beret. Panacea is a 1 owner boat sailing out of Chicago her whole life. Sails, rigging, decks, topsides, VC-17 bottom rudder and belowdecks all excellent. Recent c/v survey revealed no issues. Needs replacement engine; owner has a line on a 2010 Yanmar 20 hp with under 100 hrs and a capable marine diesel mechanic to do the install. | | |
| 34 | Hunter 34 | 1983 | | 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 | Catalina 34 MKII | 2002 | | This Catalina 34 MKII is about as spacious a cruiser as you can get under 36 feet, and she has all the amenities of larger cruising boats; such as hot water, a swim platform, large aft berth, Air Conditioning, and an enormous cockpit. Very low hours on the professionally maintained M35B. | | |
| 34 | Elan Impression 34 | 2007 | | 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. | 78,000 | |
| 36 | Hunter 36 | 2005 | | 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. | 83,000 | |
| 37 | Jeanneau Sun Odyssey 37 | 2000 | | 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! | 85,000 | |
| 36 | Catalina 36 | 1994 | | 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. | 68,000 | |
| 36 | Catalina 36MKII | 2001 | | This day sailed Lake Michigan boat is a beauty! Galt's Gulch is as turn-key ready as it gets! She is currently available for showings in St. Joe, Michigan. On July 13th she will be sailed to Chicago and be available for showings at Crowley's Yacht Yard. | | |
| 36 | Catalina 36 | 1990 | | 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 | 54,000 | |
| 37 | Jeanneau Sun Odyssey 37 | 2005 | | 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. | 83,000 | |
| 37 | Hunter Legend 37.5 | 1989 | | 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). | 48,000 | |
| 38 | Beneteau Oceanis 38 | 2014 | | The Ocenanis 38 is a sleek, modern cruiser. Quintessential features the optional shallow draft and mainsail arch over the cockpit. Not to mention the beautiful gray gelcoat with a blue boot stripe that is sure to turn heads at the dock. | | |
| 38 | Wauquiez 38 MKI | 1983 | | 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. | 45,000 | |
| 40 | Farr 38 | 1990 | | Radiance, a Bruce Farr Yacht Design #72/2 built in 1990 in Rio de Janeiro to Lloyds standards. This renown graceful hull design & sail plan is beautifully balanced making her a joy to helm. She has had the good fortune of having only two owners and the current owner over the last 24 years has spent lavishly on her including a new Beta diesel engine, updated sails, standing & running rigging, electronics, deck hardware as well as maintaining the bottom, topsides and decks to high standards. Many boats much younger don’t look nearly as good. | | |
| 40 | Jeanneau Sun Odyssey 40.3 | 2007 | | 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. | 143,000 | |
| 40 | Jeanneau Sun Odyssey 40.3 | 2007 | | She has been professionally maintained by a local marina, and is ready for her next adventure! | 135,000 | |
| 40 | Jeanneau Sun Odyssey 409 | 2015 | | This Lake Michigan boat is performance oriented with cruising comfort! She has been professionally maintained and has had annual engine maintenance. | 199,000 | |
| 40 | Beneteau Oceanis 40 | 2012 | | 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. | 175,000 | |
| 42 | Island Packet 38 | 1990 | | This Island Packet has been a Lake Michigan, day sailed cruiser! She has had 2 owners and has had excellent engine and overall maintenance. | | |
| 43 | Alden Schooner 309 | 1929 | | 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 | |
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