SAILBOATS - Scroll down for more
2003 BAVARIA 44 'LIS TIGRE' $165,000 Cdn [SALE PENDING]
1980 GULFSTAR 44 CENTER COCKPIT 'ENTRE NOUS' $165,000 Cdn
1980 GULFSTAR 44 CENTER COCKPIT 'ENTRE NOUS' $165,000 Cdn
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. The 44 is distinguished by its powerful sail plan and exceptional stability. The spacious three-cabin layout offers a level of livability that rivals larger yachts.
Toronto, Ontario
Tony Cahill at 647-385-8202
1980 GULFSTAR 44 CENTER COCKPIT 'ENTRE NOUS' $165,000 Cdn
1980 GULFSTAR 44 CENTER COCKPIT 'ENTRE NOUS' $165,000 Cdn
1980 GULFSTAR 44 CENTER COCKPIT 'ENTRE NOUS' $165,000 Cdn
The 1980 Gulfstar 44 Center Cockpit, Entre Nous, located in Picton, Ontario, is a ocean-ready blue water cruiser sailboat featuring a 75hp Yanmar diesel, in-mast furling, updated Awlgrip hull, modified 6 ft draft keel, and custom queen aft cabin.
Picton, Ontario.
PERRY at 905-999-5643
2008 HUNTER 41 'DOG DAYS' $189,000 Cdn [SALE PENDING]
2008 HUNTER 41 'DOG DAYS' $189,000 Cdn [SALE PENDING]
2008 HUNTER 41 'DOG DAYS' $189,000 Cdn [SALE PENDING]
The Hunter 41 is a masterclass in modern cruising design, drawn by the acclaimed Hunter Design Team, featuring Glenn Henderson, to deliver an ideal balance of performance, ease of handling, and immense interior volume.
Kingston, Ontario
Rob Saloman at 613-795-1734
1999 HUNTER 410 'DULCINEA' $125,000 Cdn
2008 HUNTER 41 'DOG DAYS' $189,000 Cdn [SALE PENDING]
2008 HUNTER 41 'DOG DAYS' $189,000 Cdn [SALE PENDING]
Featuring a fresh Yanmar engine, generator, A/C, and solar power, this 1999 Hunter 410 for sale in Toronto, Ontario is the ultimate 3-cabin cruiser. Discover turnkey comfort and performance with Breezeway Yachts.
Toronto, Ontario
Perry at 905-999-5643.
2009 DELPHIA 40.3 'CELTIC PIXIE' $119,000 Cdn
2009 DELPHIA 40.3 'CELTIC PIXIE' $119,000 Cdn
2009 DELPHIA 40.3 'CELTIC PIXIE' $119,000 Cdn
Explore "Celtic Pixie," a 2009 Delphia 40.3 sailboat for sale in Hamilton, Ontario. Featuring a 4 cabin, 2 head layout, 55hp Volvo diesel, 2023 Raymarine radar and chartplotter, 2400W solar, watermaker, and new MaxProp.
Comprehensive 2023 Refit: Upgraded for Modern Cruising
Hamilton, Ontario
Glenn Berglund at 905-650-2668.
1982 CHASER 39 'DARINA VI' $29,500 Cdn
2009 DELPHIA 40.3 'CELTIC PIXIE' $119,000 Cdn
2009 DELPHIA 40.3 'CELTIC PIXIE' $119,000 Cdn
The 1982 Chaser 39 "Darina VI" in Toronto, Ontario is a solid Canadian-built cruiser-racer featuring an 8,000 lb encapsulated lead keel, Harken battcar mainsail system, and Raymarine autopilot. Perfect for Lake Ontario cruising, she offers reliable performance and spacious 6'8" galley headroom.
Toronto, Ontario
Tony Cahill at 647-385-8202
2014 CATALINA 385 'MOMENTUM' $290,000 Cdn
2009 DELPHIA 40.3 'CELTIC PIXIE' $119,000 Cdn
2014 CATALINA 385 'MOMENTUM' $290,000 Cdn
This professionally maintained 2014 Catalina 385 in Kingston, Ontario features a Yanmar 40hp diesel engine, bow thruster, solar power, heat/air conditioning, and full enclosure canvas. Contact Breezeway Yachts today to explore this exceptional 5-Series sailboat for sale on Lake Ontario.
Kingston, Ontario
Perry Woodman at 905-999-5643
2000 CATALINA 380 'OVATION' $141,500 Cdn
1979 ALBERG 37 mkII 'THE EVERDEN' $46,000 Cdn
2014 CATALINA 385 'MOMENTUM' $290,000 Cdn
The 2000 Catalina 380 Ovation is a well-maintained performance cruising sailboat for sale in Toronto, Ontario. Featuring modern sails, updated Raymarine electronics, a Westerbeke diesel, and a spacious two-cabin layout, this Catalina 380 is perfectly equipped for Great Lakes cruising with Breezeway Yachts.
Toronto, Ontario
Tony Cahill at 647-385-8202
1998 CATALINA 380 'SWEETWATER' $128,500 Cdn
1979 ALBERG 37 mkII 'THE EVERDEN' $46,000 Cdn
1979 ALBERG 37 mkII 'THE EVERDEN' $46,000 Cdn
Explore "Sweetwater," a 1998 Catalina 380 sailboat for sale in Kingston, Ontario through Breezeway Yachts. Equipped with solar, wind generation, Rocna anchor, Maxprop, and full enclosure, this Catalina 380 cruiser offers twin private staterooms and exceptional Great Lakes readiness.
Kingston, Ontario
Rob Saloman at 613-795-1734
1979 ALBERG 37 mkII 'THE EVERDEN' $46,000 Cdn
1979 ALBERG 37 mkII 'THE EVERDEN' $46,000 Cdn
1979 ALBERG 37 mkII 'THE EVERDEN' $46,000 Cdn
The 1979 Whitby Alberg 37 MkII "The Everden" in Gananoque, Ontario, is a classic blue-water sailboat. Featuring modern Raymarine electronics, Yanmar diesel, solar charging, and a cozy teak interior with propane heat, this ready-to-sail cruiser is presented exclusively by Breezeway Yachts brokerage.
Gananoque, Ontario
Rob Saloman at 613-795-1734
1982 CS 36 TRADITIONAL 'OCEAN PEARL III' $51,500 Cdn
1982 CS 36 TRADITIONAL 'OCEAN PEARL III' $51,500 Cdn
1982 CS 36 TRADITIONAL 'OCEAN PEARL III' $51,500 Cdn
Discover the 1982 CS 36 Traditional, Ocean Pearl III, a premier racer-cruiser sailboat for sale in Toronto, Ontario. In very good condition, this classic CS Yachts vessel features a Westerbeke engine, solar power, and much more, perfect for Lake Ontario.
Toronto, Ontario
Tony Cahill at 647-385-8202
1981 CS 36 TRADITIONAL 'WINDREKA II' $49,000 Cdn
1982 CS 36 TRADITIONAL 'OCEAN PEARL III' $51,500 Cdn
1982 CS 36 TRADITIONAL 'OCEAN PEARL III' $51,500 Cdn
This 1981 CS 36 Traditional 'Windreka II' in Picton, Ontario, offers classic CS Yachts craftsmanship, an upgraded Westerbeke diesel, full cockpit enclosure, and robust electronics. A beautifully maintained performance cruiser ready for Lake Ontario sailing adventures.
Picton, Ontario
Rob Saloman at 613-795-1734
1980 CS 36 TRADITIONAL 'SILK PURSE' $52,000 Cdn
1982 CS 36 TRADITIONAL 'OCEAN PEARL III' $51,500 Cdn
1980 CS 36 TRADITIONAL 'SILK PURSE' $52,000 Cdn
Regarded as one of the finest production sailboats constructed in North America, the CS 36 Traditional is a masterpiece of maritime heritage, combining robust offshore build quality with swift, predictable performance. For the beautiful anchorages of Prince Edward County to an extended voyage, this vessel stands ready.
Picton, Ontario.
Perry at 905-999-5643
1979 CS 36 TRADITIONAL 'PETRICHOR' $55,000 Cdn
1979 CS 36 TRADITIONAL 'PETRICHOR' $55,000 Cdn
1980 CS 36 TRADITIONAL 'SILK PURSE' $52,000 Cdn
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.
Midland, Ontario.
Dennis Meystadt at 705-204-7377
1975 C&C 35mkII 'ILLAWARRA' $24,500 Cdn
1979 CS 36 TRADITIONAL 'PETRICHOR' $55,000 Cdn
1974 C&C 35mkII 'SECOND CHANCE' $14,500 Cdn
Explore "ILLAWARRA," a classic 1975 C&C 35 Mk II racer-cruiser for sale in Pickering, Ontario. Built by C&C Yachts, this 36-foot sailboat features recent North Sails 3DI sails, Andersen ST winches, new 2026 AGM batteries, and a comfortable layout for Lake Ontario cruising. Contact Breezeway Yachts today!
Pickering, Ontario
Tony Cahill at 647-385-8202
1974 C&C 35mkII 'SECOND CHANCE' $14,500 Cdn
1979 CS 36 TRADITIONAL 'PETRICHOR' $55,000 Cdn
1974 C&C 35mkII 'SECOND CHANCE' $14,500 Cdn
This 1974 C&C 35 mkII, SECOND CHANCE, in Whitby, ON features a Yanmar diesel, 2018 Harken furling, North Sails, upgraded electronics, and a barrier-coated hull. A proven C&C Yachts performance sailboat perfect for racing or cruising Lake Ontario with Breezeway Yachts brokerage.
Whitby, Ontario.
Tony Cahill at 647-385-8202.
2005 CATALINA 350 'PAZZO' $153,000 Cdn
1983 ENDEAVOUR 35 CUSTOM 'SAILS CALL' $49,500 Cdn
1983 ENDEAVOUR 35 CUSTOM 'SAILS CALL' $49,500 Cdn
Discover "Pazzo," a 2005 Catalina 350 sailboat for sale in Toronto, Ontario with Breezeway Yachts. Featuring an in-mast furling rig, Raymarine electronics, canvas enclosure, and two staterooms, this pristine Catalina cruiser is ready for Great Lakes adventures.
Toronto, Ontario
Tony Cahill at 647-385-8202
1983 ENDEAVOUR 35 CUSTOM 'SAILS CALL' $49,500 Cdn
1983 ENDEAVOUR 35 CUSTOM 'SAILS CALL' $49,500 Cdn
1983 ENDEAVOUR 35 CUSTOM 'SAILS CALL' $49,500 Cdn
The Endeavour 35, designed by the esteemed Bruce Kelley strikes an ideal balance between a traditional full-keel feel and modern maneuverability. This specific vessel has been updated and modified by a Custom Yacht Builder, enhancing its functionality and modernizing its profile.
Whitby, Ontario.
Tony Cahill at 647-385-8202.
1977 GODERICH 35 'NORIKO' $68,000 Cdn
1983 ENDEAVOUR 35 CUSTOM 'SAILS CALL' $49,500 Cdn
1977 GODERICH 35 'NORIKO' $68,000 Cdn
Noriko is a 1977 Goderich 35 steel cruiser designed by Ted Brewer and built by Huromic Metal Industries. Located in Kingston, Ontario, this legendary bluewater cutter features extensive refits, solar power, and exceptional sea keeping for ocean or Great Lakes cruising.
Kingston, Ontario
Rob Saloman at 613-795-1734
1984 ALOHA 34 'GENIE' $34,900 Cdn
1984 HUNTER 34 'SARABELLA' $27,000 Cdn
1984 HUNTER 34 'SARABELLA' $27,000 Cdn
Explore this upgraded 1984 Aloha 34 for sale in St Catharines, Ontario, featuring new 2025 Raymarine electronics, fresh canvas, solar charging, and new Ultraleather interior cushions.
St Catharines, Ontario
GLENN BERGLUND at 905-650-2668
1984 HUNTER 34 'SARABELLA' $27,000 Cdn
1984 HUNTER 34 'SARABELLA' $27,000 Cdn
1984 HUNTER 34 'SARABELLA' $27,000 Cdn
This 1984 Hunter 34 is a well-loved vessel, 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.
Whitby, Ontario.
Tony Cahill at 647-385-8202.
1986 C&C 33mkII 'SAGONA' $31,000 Cdn
1984 HUNTER 34 'SARABELLA' $27,000 Cdn
1986 C&C 33mkII 'SAGONA' $31,000 Cdn
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.
Whitby, Ontario.
Tony Cahill at 647-385-8202.
1983 CS 33 'PAXOS' $29,500 Cdn
1996 HUNTER 336 'BRED N WATER' $56,000 Cdn [SOLD]
1986 C&C 33mkII 'SAGONA' $31,000 Cdn
The CS 33 is widely regarded as one of the most successful designs in the CS lineup. It features a sleek profile with a relatively high ballast-to-displacement ratio, making it incredibly stiff and capable in heavy weather. It offers a comfortable salon, a functional galley, and a dedicated navigation station,
Toronto, Ontario
Tony Cahill at 647-385-8202
1996 HUNTER 336 'BRED N WATER' $56,000 Cdn [SOLD]
1996 HUNTER 336 'BRED N WATER' $56,000 Cdn [SOLD]
1996 HUNTER 336 'BRED N WATER' $56,000 Cdn [SOLD]
The Hunter 336 is widely regarded as one of the most successful designs in Hunter’s mid-size range. The "B&R Rig" eliminates the need for a backstay, allowing for a large, powerful mainsail and a smaller, easy-to-tack jib. This, coupled with a wide beam carried well aft, results in a stable, fast, and remarkably easy-to-sail vessel.
Kingston, Ontario
Rob at 613-795-1734
1986 ALOHA 32 'ANNIE'S SONG' $32,000 Cdn
1986 ALOHA 32 'ANNIE'S SONG' $32,000 Cdn
1986 ALOHA 32 'ANNIE'S SONG' $32,000 Cdn
The 1986 Aloha 32 "Annie's Song" in Kingston, Ontario, is a classic Canadian-built cruiser by Ouyang Boatworks. Featuring a Westerbeke diesel, solar charging, 2025 electric windlass, and full canvas, this ready-to-sail sailboat is presented exclusively by Breezeway Yachts brokerage.
Kingston, Ontario
Rob at 613-795-1734
2005 BENETEAU 323 'AQUAVIT' $84,500 Cdn
1986 ALOHA 32 'ANNIE'S SONG' $32,000 Cdn
1986 ALOHA 32 'ANNIE'S SONG' $32,000 Cdn
2005 Beneteau 323 "Aquavit" in Cobourg, ON. Very good condition cruiser/racer featuring a rebuilt Yanmar diesel, in-mast furling, canvas enclosure, upgraded 2024 climate control, and two-cabin layout. Offered by Breezeway Yachts, your premier boutique sailboat brokerage in Toronto, Ontario.
Cobourg, Ontario
Tony Cahill at 647-385-8202
1974 CONTESSA 32 'HEIDI II' $19,500 Cdn
1992 BENETEAU FIRST 310 'VIENTO NORTE' $49,900 Cdn [SOLD]
1992 BENETEAU FIRST 310 'VIENTO NORTE' $49,900 Cdn [SOLD]
The Legend: The Contessa 32 Experience
The Contessa 32 is globally revered as one of the most successful one-design cruiser-racers ever conceived.
Whitby, Ontario
Tony Cahill at 647-385-8202
1992 BENETEAU FIRST 310 'VIENTO NORTE' $49,900 Cdn [SOLD]
1992 BENETEAU FIRST 310 'VIENTO NORTE' $49,900 Cdn [SOLD]
1992 BENETEAU FIRST 310 'VIENTO NORTE' $49,900 Cdn [SOLD]
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.
Grimsby, Ontario
Glenn Berglund at 905-650-2668
2006 CATALINA 309 $99,000 Cdn [SOLD]
2006 CATALINA 309 $99,000 Cdn [SOLD]
2006 CATALINA 309 $99,000 Cdn [SOLD]
JUST LISTED AND SALE PENDING ON THE SAME DAY!!
Toronto, Ontario
TONY CAHILL at 647-385-8202.
1995 C&C 30mkII XL 'MOJO' $47,500 Cdn
2006 CATALINA 309 $99,000 Cdn [SOLD]
2006 CATALINA 309 $99,000 Cdn [SOLD]
This premium 1995 C&C 30 mkII XL sailboat, Mojo, is for sale in St Catharines, Ontario. Perfect for Lake Ontario racing or cruising, this very good condition fiberglass racer-cruiser features a high-performance Kevlar hybrid hull, upgraded XL tall mast, North Sails canvas, and a beautiful teak and Ultra Leather interior cabin.
St Catharines, Ontario
GLENN BERGLUND at 905-650-2668
1988 CS 30 'WU LI' $35,900 Cdn
1986 CS 30 'ORENDA' $29,500 Cdn [SOLD]
1986 CS 30 'ORENDA' $29,500 Cdn [SOLD]
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 intelligent, spacious interior layout. The CS 30 tracks beautifully and handles exceptionally well in light air and heavy weather alike.
St Catharines, Ontario
GLENN BERGLUND at 905-650-2668
1986 CS 30 'ORENDA' $29,500 Cdn [SOLD]
1986 CS 30 'ORENDA' $29,500 Cdn [SOLD]
1986 CS 30 'ORENDA' $29,500 Cdn [SOLD]
Designed for sailors who want capable performance without sacrificing comfortable cruising accommodations, the CS 30 strikes a balance that has kept it popular on Lake Ontario, throughout the Great Lakes, and across North American cruising grounds for nearly four decades.
Toronto, Ontario
TONY CAHILL at 647-385-8202.
1986 CS 30 'INTERIM 2' $27,500 Cdn
1986 CS 30 'ORENDA' $29,500 Cdn [SOLD]
1984 BAYFIELD 29 'COASTER' $22,000 Cdn
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 delights racing enthusiasts with its speed, agility, and pointing ability, while remaining stable and manageable.
Toronto, Ontario
TONY CAHILL at 647-385-8202
1984 BAYFIELD 29 'COASTER' $22,000 Cdn
1984 BAYFIELD 29 'COASTER' $22,000 Cdn
1984 BAYFIELD 29 'COASTER' $22,000 Cdn
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. This design provides excellent stability and a forgiving motion in a seaway, remaining composed and predictable. Inside, it offers a level of character that production boats struggle to replicate.
Whitby, Ontario
TONY CAHILL at 647-382-8202.
1983 NONSUCH 26 CLASSIC $33,500 Cdn
1984 BAYFIELD 29 'COASTER' $22,000 Cdn
1983 NONSUCH 26 CLASSIC $33,500 Cdn
This 1983 Hinterhoeller Nonsuch 26 Classic in Picton, Ontario, offers incredible interior space and effortless single handed cat rig sailing. Featuring a 21hp Westerbeke diesel with 780 hours, full enclosure, autopilot, and diesel heat, this premier pocket cruiser is ready for Great Lakes adventures.
Picton, Ontario
Perry at 905-999-5643