SAILBOATS for SALE
2003 BAVARIA 44 $165,000 Cdn
The Bavaria 44: A Modern Classic
The Bavaria 44 represents the sweet spot of the "J&J Design" era, a period celebrated for producing hulls with a perfect balance of volume and performance. Launched as a flagship for the private cruiser market, the 44 is distinguished by its powerful sail plan and a lead keel that provides exceptional stability in a blow. Unlike many modern "lightweight" cruisers, the 2003 model carries a reassuring heft, allowing it to slice through a chop rather than bouncing over it. It’s a blue-water capable hull dressed in the clothes of a comfortable Mediterranean coastal cruiser.
Step below deck, and the 2003 Bavaria 44 reveals why it remains a favorite for families and charterers alike. The interior is defined by rich mahogany joinery and a layout that maximizes every inch of its 13.95-meter length. With a spacious three-cabin configuration and a generous galley, it offers a level of livability that rivals much larger yachts.
Located Toronto, Ontario
Contact Tony Cahill at 647-385-8202
1980 GULFSTAR 44 CENTER COCKPIT $165,000 Cdn
Discover "Entre Nous": Your North American Adventure Awaits in this 1980 Gulfstar 44 Center Cockpit
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.
VIDEO TOUR INTERIOR VIDEO TOUR EXTERIOR
Located Picton, Ontario.
Contact PERRY at 905-999-5643
1999 HUNTER 410 $140,000 Cdn
Premium Cruising Yacht for Sale in Toronto, Ontario | Exclusively Listed by Breezeway Yachts
Discover the highly sought-after Hunter 410 in excellent freshwater condition, ready for her next owner. Located in Toronto, Ontario, Dulcineais a superb example of a well-maintained, three-cabin cruising sailboat. Exclusively represented by Breezeway Yachts, your boutique yacht brokerage serving Ontario and all of North America. This yacht offers the ideal blend of performance, comfort, and modern upgrades.
Located Toronto, Ontario
Contact Perry at 905-999-5643.
2009 DELPHIA 40.3 $119,000 Cdn
Adventure-Ready 2009 Delphia 40.3 Sailboat for Sale in Hamilton, Ontario | Located in Canada
Built by Delphia Yachts, a renowned Polish shipyard, the Delphia 40.3 is a testament to quality European boat building. This specific model is an RCD Category A vessel, certified for ocean voyages and capable of withstanding severe conditions. It combines a robust hull design with a comfortable, spacious interior, making it the ideal choice for extended cruising and liveaboard sailing. The Delphia 40.3 features a bright and inviting saloon, a fully equipped galley, and a large, well-laid-out cockpit, perfect for both long passages and entertaining at anchor.
Comprehensive 2023 Refit: Upgraded for Modern Cruising
"Celtic Pixie" has undergone a significant refit in 2023, equipping it for safe and independent "off-the-grid" sailing. The refit focused on modernizing its systems and enhancing its self-sufficiency.
Located Hamilton, Ontario
Contact Glenn Berglund at 905-650-2668.
1982 CHASER 39 $29,500 Cdn
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.
Located Toronto, Ontario
Contact Tony Cahill at 647-385-8202
1980 CS 36 TRADITIONAL $52,000 Cdn
A Canadian Cruising Legend in Prince Edward County
Breezeway Yachts is incredibly proud to present this iconic 1980 CS 36 Traditional, currently lying in the historic boating waters of Picton, Ontario. Regarded as one of the finest production sailboats ever constructed in North America, the CS 36 Traditional is a masterpiece of maritime heritage, combining robust offshore build quality with swift, predictable performance. Whether you are looking to explore the beautiful anchorages of Prince Edward County, cross Lake Ontario, or embark on an extended bluewater voyage down the Eastern Seaboard, this vessel stands ready to deliver comfort, safety, and pride of ownership.
Located Picton, Ontario.
Contact Perry at 905-999-5643
1979 CS 36 TRADITIONAL $62,500 Cdn
Breezeway Yachts is proud to present this exceptional 1979 CS 36 Traditional, currently located in the pristine waters of Midland, Ontario. For sailors seeking an authentic blend of timeless pedigree, rugged build quality, and spirited performance, few vessels command as much respect in the Great Lakes and beyond as the iconic CS 36. Renowned as a premier racer-cruiser, this classic monohull represents a golden era of Canadian boatbuilding, offering a Turn-key opportunity for local cruising on Georgian Bay or blue-water adventures across North America.
Located Midland, Ontario.
Contact Dennis Meystadt at 705-204-7377
1974 C&C 35mkII $14,500 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.
1983 ENDEAVOUR 35 CUSTOM $49,500 Cdn
The Endeavour Legacy: Built for the Blue
The Endeavour 35, designed by the esteemed Bruce Kelley, was one of the firm's most successful models. It strikes an ideal balance between a traditional full-keel feel and modern maneuverability. While the standard 35 is known for its spacious interior and reliable sloop rig, this specific vessel has been updated and modified by a Custom Yacht Builder, enhancing its functionality and modernizing its profile for today’s cruising standards.
Located Whitby, Ontario.
Contact Tony Cahill at 647-385-8202.
1984 HUNTER 34 $27,000 Cdn
1984 Hunter 34
The Hunter 34 (built by the renowned Hunter Marine) is a celebrated cruising sailboat known for its spacious interior, comfortable amenities, and solid performance. Designed for easy handling and enjoyable family cruising, this vintage sail yacht represents an excellent opportunity for a new owner to step into the world of yachting without a major investment. This specific 1984 Hunter 34 is a well-loved vessel in average condition, ready for its next adventure on Lake Ontario or beyond. It offers a great platform for the budget-conscious sailor seeking a reliable mid-30s cruiser with the classic lines and livability that Hunter is famous for.
Located Whitby, Ontario.
Contact Tony Cahill at 647-385-8202.
1986 C&C 33mkII $31,000 Cdn
The C&C 33 mkII: A Perfect Balance of Speed and Comfort
The 1986 C&C 33 mkII represents the absolute pinnacle of C&C’s mid-sized cruiser design evolution. Striking the ideal balance between a spirited club racer and a comfortable weekend family cruiser, the mkII variant features an updated hull shape and a highly efficient keel-stepped mast configuration. It is designed to track beautifully, point high into the wind, and provide a stable, confidence-inspiring ride under sail, making it a favorite for single-handed sailing or full-crew racing on the Great Lakes.
Located Whitby, Ontario.
Contact Tony Cahill at 647-385-8202.
1983 CS 33 $29,500 Cdn
The CS 33: A Modern Classic
The CS 33 is widely regarded as one of the most successful designs in the CS lineup. Launched as a follow-up to the popular CS 27 and 36, the 33-footer hit the "sweet spot" for many sailors. It features a sleek profile with a relatively high ballast-to-displacement ratio, making it incredibly stiff and capable in heavy weather. It’s a boat that inspires confidence when the wind picks up, yet remains light and responsive on the helm during gentle summer breezes. Below deck, the CS 33 shines with an interior layout that feels much larger than its footprint suggests. With a generous beam and clever use of space, it offers a comfortable salon, a functional galley, and a dedicated navigation station—all finished with the rich teak joinery that CS is famous for.
Located Toronto, Ontario
Contact Tony Cahill at 647-385-8202
1996 HUNTER 336 $56,000 Cdn [SALE PENDING]
The Hunter 336: A Modern Cruiser Ahead of Its Time
The Hunter 336 is widely regarded as one of the most successful designs in Hunter’s mid-size range. It was a pioneer in incorporating the "B&R Rig," which eliminates the need for a backstay, allowing for a large, powerful mainsail and a smaller, easy-to-tack jib. This design choice, coupled with a wide beam carried well aft, results in a stable, fast, and remarkably easy-to-sail vessel that excels in the varied conditions of the Great Lakes. e Hunter 336 is a true "pocket cruiser" that offers the amenities and elbow room usually reserved for 36-footers.
Located Kingston, Ontario
Contact Rob Saloman at 613-795-1734
2005 BENETEAU 323 $97,000 Cdn
Beautiful 2005 Beneteau 323 for Sale – The Family Cruising Experience in Oakville, Ontario
Experience the perfect blend of French elegance and performance with this exceptionally maintained 2005 Beneteau 323, now available through Breezeway Yachts. Currently located in Oakville, Ontario, this vessel represents a rare opportunity to own a modern cruiser that has been extensively upgraded for comfort, efficiency, and ease of handling.
NOTE: The vessel is under a low profile cover, pictures were from the time of the previous listing in 2020.
Located Oakville, Ontario
Contact Glenn Berglund at 905-650-2668
1992 BENETEAU FIRST 310 $49,900 Cdn
The Beneteau First 310, designed by the renowned Group Finot, is a standout model in the builder's celebrated "First" lineage. Known for striking a perfect balance between a fast cruiser and an agile club racer, the 310 features a modern, easily driven hull form paired with a powerful rig. Below the waterline, the cast iron fin keel and responsive spade rudder offer excellent stability, impressive tracking, and a light helm that delights single-handed sailors and full crews alike.
Located Grimsby, Ontario
Contact Glenn Berglund at 905-650-2668
2003 CATALINA 310 $97,500 Cdn [SOLD]
Newly Listed and Already SOLD!!
Located Toronto, Ontario.
Contact Tony Cahill at 647-385-8202.
2001 CATALINA 310 $72,500 Cdn [SOLD]
1981 NIAGARA 31 $27,000 Cdn [SALE PENDING]
Classic Canadian Racer-Cruiser -The Hinterhoeller Niagara 31
Discover the exceptional sailing pedigree of the 1981 Niagara 31, a beloved Canadian-built racer-cruiser now available. Designed by the renowned naval architect Germán Frers and built by the legendary Hinterhoeller Yachts in St. Catharines, Ontario, the Niagara 31 is celebrated for its solid construction, elegant lines, and superb performance. This well-maintained sloop is in good condition and has seen many recent upgrades, making her a truly turnkey option for your next sailing season. Whether you're looking for a capable club racer, a comfortable weekend cruiser, or a trustworthy vessel for extended Great Lakes voyages, this used sailboat for sale in Ontario is an opportunity not to be missed.
Located in Whitby, Ontario
Contact TONY CAHILL at 647-385-8202.
2006 CATALINA 309 $99,000 Cdn [SOLD]
JUST LISTED AND SALE PENDING ON THE SAME DAY!!
Located in Toronto, Ontario
Contact TONY CAHILL at 647-385-8202.
1995 C&C 30mkII XL $47,500 Cdn
The C&C 30mkII is widely considered one of the finest 30-foot sailboats ever designed, and the "XL" (Extra Light/Extended Performance)version is its ultimate evolution. Designed by Rob Ball, the 30mkII features a modern, fair hull shape and an optimized underwater profile. The XL package elevates this design to a true performance tier, featuring a Kevlar hybrid fabric construction for unmatched hull stiffness, a deeper lead bulb keel for enhanced righting moment, and an upgraded triple-spreader mastwith Navtec rod rigging.
Located St Catharines, Ontario
Contact GLENN BERGLUND at 905-650-2668
1988 CATALINA 30 $35,000 Cdn [SOLD]
JUST LISTED and already SOLD!!
Located in Toronto, Ontario
Contact TONY CAHILL at 647-385-8202.
1988 CS 30 'WU LI' $35,900 Cdn
Designed by the legendary Tony Castro, the CS 30 is widely considered one of the finest 30-foot performance cruisers ever built. Castro successfully merged a fast, modern hull shape with an incredibly intelligent, spacious interior layout that makes the boat feel like a 32-to-34-foot vessel. With a well-proportioned sail plan, responsive wheel steering, and an efficient underbody, the CS 30 tracks beautifully and handles exceptionally well in light air and heavy weather alike, making it the perfect racer-cruiser for Lake Ontario and beyond.
Located St Catharines, Ontario
Contact GLENN BERGLUND at 905-650-2668
1986 CS 30 'INTERIM 2' $35,900 Cdn
Designed by the renowned British naval architect Tony Castro, the CS 30 revolutionized the 30-foot cruiser market when it debuted. Castro successfully married a sleek, modern, performance-oriented hull underbody with an incredibly spacious, ergonomic interior plan. The result is a sailboat that delights racing enthusiasts with its speed, agility, and pointing ability, while remaining stable, manageable, and forgiving enough for single-handed or family pocket-cruising.
Located in Toronto, Ontario
Contact TONY CAHILL at 647-385-8202
1985 CS 30 $33,500 Cdn [SOLD]
SOLD!!
Located in Whitby, Ontario
Contact TONY CAHILL at 647-385-8202.
1984 BAYFIELD 29 $22,000 Cdn
The Bayfield 29: A Pocket Cruiser with Soul
Designed by Gozzard himself, the Bayfield 29 features a full keel with a shallow draft of only 3'6", making it an ideal candidate for gunkholing in thin water or navigating the Intracoastal Waterway. Its most striking feature is the functional bowsprit, which extends its profile and allows for a versatile cutter rig setup. This design provides excellent stability and a forgiving motion in a seaway, ensuring that even when the whitecaps start to show, the 29 remains composed and predictable.
Inside, the Bayfield 29 punches well above its weight class. Thanks to a clever interior layout that omits a traditional forward bulkhead in favor of an open, airy feel, the cabin feels significantly larger than most 29-footers of its era. It offers a level of comfort and "cozy ship" character that modern production boats struggle to replicate.
Located in Whitby, Ontario
Contact TONY CAHILL at 647-382-8202.
2005 CATALINA 28mkII $65,000 Cdn [SOLD]
The Perfect Great Lakes Cruiser: Catalina 28 MkII
Rarely available on Georgian Bay, this beautifully maintained 2005 Catalina 28 MkII is the ideal family cruiser, combining the legendary comfort and robust build quality of Catalina Yachts with modern features and essential upgrades.
Located in Lion's Head, Ontario, on the scenic Bruce Peninsula, this vessel features the highly desirable Wing Keel (3'9" Draft), providing superior stability and the ability to explore the shallow, pristine anchorages of Lake Huron and Georgian Bay that deeper keels cannot reach.
Located in Lion's Head, Ontario
Contact DENNIS MEYSTADT at 705-204-7377.