SAILBOATS for SALE
1980 GULFSTAR 44 CENTER COCKPIT $165,000 CDN
Discover "Entre Nous": Your North American Adventure Awaits in this 1980 Gulfstar 44 Center Cockpit
Embark on your next grand journey aboard "Entre Nous", a meticulously maintained 1980 Gulfstar 44 Center Cockpit sailboat. This isn't just any used boat for sale; she's a testament to the golden age of American boatbuilding, renowned for her exceptional cruising comfort, clever design, and timeless nautical charm. Located in Picton, Ontario, this 44-foot Gulfstar is available through Breezeway Yachts, your specialized boutique brokerage with North American reach.
A Proven Cruiser, Repowered for Reliability
Designed by the legendary Vince Lazzara, the Gulfstar 44 Center Cockpit is an ideal liveaboard or long-range passage maker. Her solid fiberglass hull offers exceptional strength and stability, ensuring a secure and comfortable motion on any body of water, from the Great Lakes to distant shores.
"Entre Nous" has been thoughtfully repowered with a trusted Yanmar 75hp Turbo Diesel engine, providing reliable and efficient propulsion for your adventures. This used sailboat combines classic lines with modern peace of mind, making her as dependable as she is beautiful.
Located Picton, Ontario.
Contact PERRY at 905-999-5643
2012 CATALINA 445 $289,500 USD [SOLD]
This 2012 Catalina 445 is a cruising dream yacht, equipped to the max for long range sailing and live aboard life.
Soundwave NB is a Canadian Federally Registered vessel. No Canadian taxes apply for US Buyers, and there is no duty to import into the US.
The Catalina 445 was Boat of the Year when introduced in 2009. Her 5 foot wing keel, stiffened hull, and tall rig make her quick on long passages. Easy sail handling from the cockpit, wide weather decks, and spacious dual helm cockpit give the captain and crew confidence while at sea. Fast and strong, she is ideal for a couple with long range cruising in mind. The "third" cabin which can be used as a "garage", tool room, massive storage locker or a spare double cabin provides plenty of flexibility.
Located near Moncton, NB.
Contact GLENN BERGLUND at 905-650-2668.
1997 CATALINA 42mkII $199,000 Cdn [SOLD]
JUST LISTED.
Spacious 2 Cabin, Pullman Configuration. Full Enclosure with newer Canvas, Cockpit Cushions, Custom Cockpit Sole Insert.
Newer House Batteries, Battery Charger, Solar.
Wing Keel shoal draft, Newer Main and Genoa and most Running Rigging. Electric Halyard Winch, Standard Horizon GPS Plotter, Newer Windlass, Rocna Anchor and lots more.
This well maintained cruiser is a two owner, always freshwater boat.
Located in Kingston, Ontario.
Contact ROB SALOMAN at 613-795-1734
1982 CHASER 39 $33,500 Cdn
JUST LISTED
Your Next Sailing Adventure Awaits
Step aboard this exceptional 1982 Chaser 39, a testament to rugged Canadian craftsmanship and classic sailing performance. Built to last with a unique monocoque construction (meaning a continuous, watertight hull-to-deck bond), this vessel provides a secure and stable ride in any conditions. The Chaser 39 is renowned for its strength, featuring an 8,000 lb encapsulated lead ballast and GRP encapsulated balsa stringers. The topsides have been recently painted with two-component Epiphanies paint, giving her a refreshed look.
This beautiful sailboat, available exclusively through Breezeway Yachts, is perfectly equipped for cruising the beautiful waters of Lake Ontario, Georgian Bay, and beyond. Her capabilities are well-suited for exploring North America's diverse inland and coastal waterways, offering a reliable platform for everything from weekend regattas to extended cruises.
Located Toronto, Ontario
Contact Tony Cahill at 647-385-8202
1988 C&C 38mkIII
Experience "Windstar III"
A Custom 1980 C&C 38mkIII Freshwater Gem with Extensive Upgrades
Discover "Windstar III", an exceptional 1980 C&C 38 custom sailboat that truly stands out in the Ontario used boat market. This isn't just a classic; it's an updated freshwater vessel featuring recent upgrades that make her ready for adventures on Lake Ontario and beyond. Available exclusively through Breezeway Yachts, your boutique used boat brokerage near Toronto, "Windstar III" offers a unique blend of custom craftsmanship and modern reliability.
Located Pickering, Ontario
Contact Tony Cahill at 647-385-8202
2004 CATALINA 36mkII $124,500 Cdn
Discover This Exceptional 2004 Catalina 36mkII - Your Next Ontario Sailing Adventure Awaits!
Step aboard this beautiful 2004 Catalina 36mkII, a shining example of North America's most popular 36-foot cruising sailboat. This rare fin keel and standard main version offers the perfect blend of comfort, smart design, and exhilarating performance, whether you're relaxing at the dock or underway on the beautiful waters of Ontario. Available exclusively through Breezeway Yachts, your boutique used boat brokerage near Toronto, this Catalina is ready for its next discerning owner.
Located Toronto, Ontario
Contact Tony Cahill at 647-385-8202
1974 C&C 35mkII $17,500 Cdn
Experience Classic Performance
1974 C&C 35 MkII Racer/Cruiser for Sale in Ontario
Discover the elegant 1974 C&C 35 MkII, a distinguished racer/cruiser that perfectly blends performance with comfort. This timeless vessel offers an exceptional opportunity for sailing enthusiasts looking for a capable and charming used sailboat in the Ontario market. Available through Breezeway Yachts, your boutique used boat brokerage near Toronto, this C&C 35 MkII promises an enjoyable journey whether you're racing around the marks or cruising at leisure.
Located Whitby, Ontario.
Contact Tony Cahill at 647-385-8202.
1985 O'DAY 35 $43,500 Cdn [SALE PENDING]
Explore the 1985 O'Day 35 - An Affordable Cruising Sailboat Ready for Ontario Adventures!
Set sail on your next adventure with this well-equipped 1985 O'Day 35, asking $43,500 Cdn. This classic cruising sailboat offers an exceptional blend of comfort, practicality, and affordability, making her an ideal choice for new sailors or those looking to explore the beautiful waters of Ontario. Available exclusively through Breezeway Yachts, your specialized boutique used boat brokerage near Toronto, this O'Day is a fantastic opportunity for freshwater enjoyment.
Located Picton, Ontario.
Contact Chris Verra at 613-885-1482.
1997 BENETEAU OCEANIS 321 $69,500 Cdn
Newly Listed
The Beneteau Oceanis 321 holds a special place in the hearts of sailors for its remarkable combination of performance, comfort, and user-friendly design. It’s a vessel that truly punches above its weight. Designed to excel in both lively competitive races and leisurely family cruises, this model’s spacious interior feels much larger than its 32-foot length suggests. The wide beam and intelligently crafted layout create a stable and inviting atmosphere below deck, perfect for relaxing after a day on the water. Meanwhile, the efficient hull shape and rigging provide a dependable, exhilarating sailing experience that instills confidence in new and seasoned sailors alike. Known for its quality construction and timeless aesthetic, the Beneteau 321 remains a highly sought-after sailboat for anyone looking to explore the water with assurance and style.
Located Pickering, Ontario.
Contact Tony Cahill at 647-385-8202.
2008 CATALINA 320mkII $104,900 Cdn [SALE PENDING]
Just Listed: 2008 Catalina 320mkII
The Perfect Ontario Cruiser!
Introducing a truly exceptional find: this JUST LISTED 2008 Catalina 320mkII. Renowned for its comfortable accommodations and stellar performance, the Catalina 320mkII is a highly sought-after model, and this one is no exception. Located in St Catharines, Ontario, and offered exclusively through Breezeway Yachts, your boutique used boat brokerage near Toronto, this vessel is ideally equipped for effortless cruising on Lake Ontario and beyond.
Located St Catharines, Ontario
Contact Glenn Berglund at 905-650-2668.
1989 PEARSON 31-2 $32,900 Cdn
"Sailavie": Discover This 1989 Pearson 31-2 - Perfect for Safe Family Cruising in Ontario!
Introducing "Sailavie," a fantastic 1989 Pearson 31-2 that stands out as a top choice for family cruising and enjoyable performance. This popular design is celebrated for its comfortable interior, excellent sailing characteristics, and versatility for both relaxed cruising and spirited club racing. With its thoughtful features and recent upgrades, "Sailavie" is an ideal used sailboat for exploring the beautiful waters of Ontario. Available through Breezeway Yachts, your specialized boutique brokerage near Toronto, she promises memorable moments on the water.
Located Kingston, Ontario.
Contact ROB SALOMAN at 613-795-1734.
1995 C&C 30mkII XL $61,500 Cdn
"Mojo": Experience this Custom 1995 C&C 30 MkII XL - A Freshwater Racer/Cruiser Gem!
Introducing "Mojo," the distinguished last of the C&C 30 MkII series, built in 1995 as Hull #176. This isn't just any used sailboat; she's a highly sought-after MkII-XL variant, boasting significant factory upgrades to her racing capabilities, seamlessly integrated with a beautifully appointed interior. Located in Alberta, "Mojo" offers an unparalleled opportunity for sailors seeking a high-performance racer/cruiser that's equally comfortable for extended adventures on Lake Ontario and beyond. Available through Breezeway Yachts, your boutique used boat brokerage near Toronto, "Mojo" comes complete with an invaluable custom trailer, ready for North American exploration.
Mojo is the last of the C&C 30mkII's built in 1995. She is hull # 176 of the 176 built, and fitted as a mkII-XL.
Located Alberta
Contact PERRY WOODMAN at 905-999-5643.
1974 C&C 30mkI $15,000 Cdn [SOLD]
1974 C&C 30 Mk I | Very Clean & Well-Maintained | Located in Pickering, Ontario
Discover Classic C&C Performance and Pride of Ownership
Breezeway Yachts is proud to present this exceptional 1974 C&C 30 Mk I, a testament to Canadian yacht building and meticulous care. Showing immense pride of ownership, this sailboat is remarkably clean and in good condition for her age, reflecting years of dedicated maintenance by her current owner. She offers the perfect blend of performance and comfort, making her an ideal choice for a spirited club racer or a comfortable weekend cruiser.
The C&C 30 Mk I is renowned for its responsive handling and comfortable interior, a hallmark of C&C design. This particular vessel stands out with her evident cleanliness, inviting you to step aboard and enjoy immediately.
Located Pickering, Ontario.
Contact TONY CAHILL at 647-385-8202.
1992 CATALINA 30mkII $35,000 Cdn [SOLD]
SUMMER DOCKAGE 2025 INCLUDED IN PURCHASE.
Two Owner, Freshwater Catalina 30mkII, features Universal 25hp XP Diesel, Gori 2 Blade Folding Prop, Lead Fin Keel and more.
Located Kingston, Ontario.
Contact ROB SALOMAN at 613-795-1734.
1977 WESTSAIL 28 $35,000 Cdn
"Mimosart": Discover This Rare 1977 Westsail 28 Cutter - A Meticulously Restored Classic for Ontario Cruising!
Introducing "Mimosart," an exceptionally rare and beautifully maintained 1977 Westsail 28 Cutter. This isn't just any used sailboat; she's a factory-finished gem, built with nearly every available option, including a stunning full teak deckthat exudes timeless nautical elegance. Located in Port Credit, Ontario, "Mimosart" offers a unique opportunity for discerning sailors to own a truly capable and classic cruiser. Available through Breezeway Yachts, your specialized used boat brokerage in the Greater Toronto Area [GTA], "Mimosart" is ready for decades more of memorable adventures on Lake Ontario and beyond.
Located in Port Credit, Ontario
Contact TONY CAHILL at 647-385-8202.
1985 HALMAN HORIZON 27 $14,500 Cdn
Discover "Horizon": A Classic 1985 Halman Horizon 27 Cutter - Your Freshwater Adventure Awaits in Ontario!
Introducing "Horizon," a charming and capable 1985 Halman Horizon 27 Cutter, asking $14,500 Cdn. This beloved Canadian-built sailboat is a true classic, originally crafted right here in Beamsville, Ontario. With her distinctive cutter rig, elegant bowsprit, and graceful canoe stern, "Horizon" is as aesthetically pleasing as she is capable on the water. Located in St. Catharines, Ontario, this freshwater boat offers an incredible opportunity for sailors seeking an affordable, robust, and character-filled cruiser. Available through Breezeway Yachts, your specialized used boat brokerage in the Greater Toronto Area [GTA], "Horizon" is ready for exploring Lake Ontario and beyond.
Located St Catharines, Ontario.
Contact Glenn Berglund at 905-650-2668.