| 30
| Nonsuch 30 Ultra
| 1987
| Winds of Change
| Winds of Change is a cat rig with free standing/unstayed aluminum mast and wishbone boom. Easy for single-handed/short-handed sailing; hoisting, tacking, and reefing.
| 28,000
| 
|
| 30
| Sabre 30
| 1981
| Stained Blue
| Stained Blue is an always Sabre freshwater boat in very good condition. Annual preventive and corrective maintenance by the current and former owners. Upgrades since 2021 include, new Raymarine electronics, battery charger, new lithium batteries, cockpit speakers and more. Custom winter cover.
| 22,000
| 
|
| 30
| Hunter 30
| 1994
| Graceful Rose
| Graceful Rose is a classic Hunter 30 designed for cruising enthusiasts. Electronics include standard Depth/Speed, GPS, VHF, shorepower, battery charger and stereo/speakers. In August 2025, two brand new batteries were installed.
| 18,000
| 
|
| 30
| Hunter 30
| 1978
| Ambitious
| For her age Ambitious is in outstanding condition. She has been primarily day-sailed off Chicago. Her “middle” owner had her from 1983 to 2021 moored on a can in Monroe St. Harbor. Over the years, she has received routine annual maintenance and belowdecks, excellent cosmetic upgrades. Equipped with Garmin electronics including a Garmin autohelm. Batteries are new in 2023.
| 13,000
| 
|
| 32
| Kettenburg 32
| 1978
| Queen Molly's Revenge
| Queen Molly's Revenge has been seen sailing in Lake Michigan for the past 20 years. Upgraded to Beta diesel engine in 2007. Annual engine maintenance and winterization. Windlass on deck and healthy sails - Main (2021).
| 12,000
| 
|
| 32
| Catalina 320
| 1998
| Rat Race
| Rat Race is a 2-owner boat always sailed in Chicago area. Yearly professional maintenance and recent Garmin electronic upgrades in 2020 - Chartplotter, GPS and VHF.
| SOLD
| 
|
| 33
| Beneteau First 10R
| 2007
| Black Magic
| Black Magic is rigged with carbon fiber main sail (2025) and carbon headsail. This boat is upgraded with a carbon rudder and retractable bow sprit. The mast, boom, spreaders and boot stripes are newly painted 2024. The brand-new running rigging feeds through Harken blocks, cam cleats, Spinlock clutches and Lewmar self-tailing winches.
| SOLD
| 
|
| 33
| C&C 33-2
| 1985
| Alternate Reality
| Alternate Reality is a clean C&C 33-2 with many improvements and upgrades. This boat is ready for cruising or offshore racing. She's electronically fitted with Garmin wind/depth/speed (2015) and chartplotter. A Raymarine autopilot was added in 2014. Some running rigging replaced in 2023.
| SOLD
| 
|
| 33
| Hunter 33
| 2005
| Rocinante
| Rocinante is a freshwater Hunter 33 that has been professionally maintained and received extensive upgrades within the past three seasons including new sails. Additionally, interior upholstery was professionally redone, and a dodger was fabricated. The 12V system has been upgraded to a lithium battery bank with compatible 110V charger. USB-C charging ports added throughout AC and DC system.
| 55,000
| 
|
| 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
| Pacific Seacraft Ericson 34
| 1992
| Nomad
| Nomad is a Pacific Seacraft Ericson 34 with a wing keel. Built by Ericson Yachts in 1992. This boat is equipped with a 32 HP Volvo diesel engine - only around 300 hours.
| SOLD
| 
|
| 34
| Pacific Seacraft 34
| 1991
| Harper Leigh
| Harper Leigh is durable and dependable double ender that is well built and balanced.
| SOLD
| 
|
| 34
| Pacific Seacraft 34
| 1997
| Felicity
| Felicity is an exceptional example of the renowned Pacific Seacraft 34, a yacht celebrated for her offshore pedigree, gentle motion, and timeless beauty. This two-owner Great Lakes vessel has been freshwater-sailed since new, and in the past four years has undergone a comprehensive refit—bringing her equipment, rig, and systems entirely up to date while preserving her classic charm.
| 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.
| 56,000
| 
|
| 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.
| SOLD
| 
|
| 36
| Beneteau First 36.7
| 2003
| Sorcerer
| Sorcerer is a turn-key racer/cruiser with many upgrades over the years. Full service annual engine maintenance. Professional shrink wrap and winterization every year. In 2018, upgraded to Raymarine Autopilot. Includes original B&G electronics throughout. Comes with a custom made cradle and an extensive sail inventory.
| 69,000
| 
|
| 36
| C&C 110
| 2007
| Fantastic
| Fantastic is a 2007 always fresh water, one-owner, 6’ draft C&C 110 by Tartan with carbon fiber mast and Volvo sail drive (approx. 600 hours). Decks, topsides, bottom and belowdecks all in almost-new condition.
| 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
| 
|
| 37
| Chris Craft Apache 37
| 1969
| Isabelle
| Isabelle was designed to be a "gentleman's racer." She was restored and renamed Isabelle because she is, Queen of The Lake. She blends together good livability and a sea kindly motion, with a well performing hull and rig combination that can be single or shorthanded. She has a distinct look that turns heads and invites inquiries and compliments when she enters a harbor or is at dock. She is extremely safe even in inclement weather. Isabelle has had 4 owners and moved to the cold, clean, freshwaters of Lake Michigan after she raced from Rhode Island to Bermuda her first year.
| 24,000 UA
| 
|
| 37
| Beneteau Oceanis 37
| 2011
| Serene
| Serene is a one owner (super maintenance focused) boat since 2012. Belowdecks she is spacious and “Boatshow clean.” Heat/AC, electric flush head.5 yr old UK carbon furling mainsail and headsails plus asym spin with Selden sprit. Located in Kenosha, WI. Winter storage included with purchase.
| 130,000
| 
|
| 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
| 
|
| 38
| Beneteau Oceanis 38.1
| 2017
| Grey Havens
| Grey Havens is a clean and beautiful turn-key sailboat. On deck equipped with windlass, bow thruster, B&G chartplotter and electronics. Interior accommodations include Dometic AC/Heater, electric toilet, flat screen TV and more!
| 195,000
| 
|
| 38
| Beneteau Oceanis 38
| 2016
| Moonshadow
| Moonshadow is clean and well-kept, almost new on and belowdecks, silky smooth bottom. Super low engine hours. In mast furling mainsail, bow thruster, electric windlass.
| 198,000
| 
|
| 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. Professional Full-Service Winterizing Fall 2025.
| 108,000
| 
|
| 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.
| SOLD
| 
|
| 43
| Jeanneau Sun Odyssey 439
| 2014
| Eclipse
| Eclipse is a 2014 Jeanneau Sun Odyssey 439 in great condition. Currently outside at Crowley's Yacht Yard in Chicago, IL with shrink wrap and winterization 2025. Rigged with lazy jacks and a stack pack. Powered by an inboard diesel engine with sail drive and 3-blade folding propellor from Flexofold. Dual steering with carbon fiber wheels by Carbonautica. B&G Chart Plotter and electronics.
| 200,000
| 
|
| 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.
| SOLD
| 
|
= Marine Survey and/or Mechanical Systems Evaluation Report available.
= Price recently reduced.
