Four Winns Cuddy Boats for sale

1993 Four Winns 285 Express

$17,950

Page, Arizona

Year 1993

Make Four Winns

Model 285 Express

Category Cuddy Cabins

Length 28

Posted 1 Month Ago

This 1993 Four Winns 285 Express is in outstanding condition according to the seller. Professionally maintained and according to the owner, there are no outstanding maintenance needs. Full service earlier this year. Upholstery showing some signs of aging but overall in very good condition. The trailer has issues with it's brakes. Guts of one of the wheels is missing the brakes and it is unsure if any of the brakes work. Also, part of the windshield has been replace with plexiglass and may be a safety hazard. Stock #351172 Excellent and Clean Condition! Very Low Hours! Well Maintained! Many New Upgrades and Additions! Ready for the Summer Season! Outstanding opportunity to purchase this 1993 Four Winns 285 Espress in outstanding condition. This may be a little on the older side but it has been extremely well cared for. Pushed by twin OMC Cobra 5.0 EFI engines with 300 horse power each, ready to hit the lake. Full bimini as well as newer isinglass enclosure to protect you from the sun and the elements. Large bow sleeping area full kitchen with a stove, microwave and a mini-refrigerator. Full bathroom with a toilet, sink and as spray-down shower along with 50 gallon fresh water tank. There is a heater and a free standing Harrier air conditioner that will go with the vessel. Perfect weekender or live aboard. Comes with a triple axle trailer so you can take it home with you. Give us a call we are hear to help with questions and ready for your offer. Reason for selling is not using enough to keep. time for someone else to enjoy it..

1993 Four Winns 285 Express

$17,950

Page, Arizona

Year 1993

Make Four Winns

Model 285 Express

Category Cuddy Cabins

Length 28

Posted 1 Month Ago

This 1993 Four Winns 285 Express is in outstanding condition according to the seller. Professionally maintained and according to the owner, there are no outstanding maintenance needs. Full service earlier this year. Upholstery showing some signs of aging but overall in very good condition. The trailer has issues with it's brakes. Guts of one of the wheels is missing the brakes and it is unsure if any of the brakes work. Also, part of the windshield has been replace with plexiglass and may be a safety hazard. Stock #351172 Excellent and Clean Condition! Very Low Hours! Well Maintained! Many New Upgrades and Additions! Ready for the Summer Season! Outstanding opportunity to purchase this 1993 Four Winns 285 Espress in outstanding condition. This may be a little on the older side but it has been extremely well cared for. Pushed by twin OMC Cobra 5.0 EFI engines with 300 horse power each, ready to hit the lake. Full bimini as well as newer isinglass enclosure to protect you from the sun and the elements. Large bow sleeping area full kitchen with a stove, microwave and a mini-refrigerator. Full bathroom with a toilet, sink and as spray-down shower along with 50 gallon fresh water tank. There is a heater and a free standing Harrier air conditioner that will go with the vessel. Perfect weekender or live aboard. Comes with a triple axle trailer so you can take it home with you. Give us a call we are hear to help with questions and ready for your offer. Reason for selling is not using enough to keep. time for someone else to enjoy it..

1996 Four Winns 245 Sundowner

$16,000

Littleton, Colorado

Year 1996

Make Four Winns

Model 245 Sundowner

Category Cuddy Cabin Boats

Length 24

Posted 1 Month Ago

This vessel has all features functional working well claims the seller. Boat has been maintained and winterized by local dealer to help maintain its engine. The deck feels firm and strong without any indication of any soft spots. The vinyl on the vessel shows its age in certain areas. Stock #353643 Four Winn 245 Sundowner Introducing the 1996 Four Winns 245 Sundowner: Are you ready to embark on your next boating adventure? Look no further than the Four Winns 245 Sundowner. This sleek and stylish giant cuddy boat offers a perfect blend of power, performance, and interior comfort. One of the standout features of this remarkable boat is its powerful Volvo Penta engine, paired with a duo prop outdrive. Whether you're cruising along calm waters or exploring more challenging conditions, this combination ensures enhanced maneuverability and exceptional performance, giving you the confidence to handle any situation easily. Its long-term freshwater history sets the Four Winns 245 Sundowner apart from the rest. This means that the vessel, as the seller says, it has been well cared for and used exclusively in freshwater environments by them. Another impressive aspect of this vessel is its low hours for its vintage. Step aboard the 1996 Four Winns 245 Sundowner, and you'll find a larger than average comfortable interior that truly stands the test of time. The spacious cabin allows for overnight stays, accommodating up to four people. The well-appointed forward berth provides a cozy and inviting retreat after a day of adventure. Outside, the Four Winns 245 Sundowner boasts a spacious cockpit area with generous seating for all your guests. The wraparound lounge seating and adjustable captain's chair ensure everyone can relax and enjoy the breathtaking views. The cockpit features a wet bar, perfect for entertaining and keeping refreshments close at hand. This 1996 Four Winns 245 Sundowner with its Volvo Penta engine, duo prop outdrive, long-term freshwater history, and low hours, this vessel is sure to impress even the most discerning boating enthusiast. Reason for selling is not using enough.

2005 Four Winns 205 Sundowner

$19,500

Phoenix, Arizona

Year 2005

Make Four Winns

Model 205 Sundowner

Category Cuddy Cabin Boats

Length 20

Posted 1 Month Ago

According to the seller, This Four Winns Sundowner is in outstanding condition inside and out. There were no signs of dents, dings or scratches to the hull. All systems and equipment operate as designed according to the seller. Stock #375841 205 Sundowner powered by a Mercruiser stern drive engine! This is a tremendous opportunity to purchase this 2005 Four Winns Sundowner in outstanding condition. This Sundowner is pushed by the powerful Mercruiser engine with an Alpha One stern drive. This Sundowner is a great family boat and seats 9 comfortably. It has a V-berth that can sleep 2 and has a porta-potty. This Sundowner is perfect for family fun including skiing, tubing, wakeboarding or just cruising the lake. Don't miss this great opportunity to get this Four Winns Sundowner at a very good price. Please call, email or text with questions or to make an offer. Reason for selling is not using as much anymore.

1992 Four Winns 205 Sundowner

$11,750

Hanford, California

Year 1992

Make Four Winns

Model 205 Sundowner

Category Cuddy Cabin Boats

Length 20

Posted 1 Month Ago

1992 Four Winns 205 Sundowner appeared to be in good operating condition and there was no damage to the boat that was evident. All systems were said to be operational. Stock #250029 Excellent condition 205 Sundowner! Extras included! Ready to hit the water and cruise! This is a 1992 Four Winns 205 Sundowner powered by a 5.7L V8 producing 270 horsepower. This is a good boat for all-around fun or for those who like to fish. Also included is a full enclosure to give you protection from the elements and it's 18 months old and looks brand new. Also included is a bimini top. New hatch up front, new Humminbird electronics for fishing and navigation, as well as a new stereo. The cuddy cabin can sleep two comfortably and you can sleep two people on the deck as well. Full passenger capacity is 10. This boat is ready to hit the water today and it's priced exceptionally well. Don't wait, call us today! Reason for selling is unable to use anymore.

2006 Four Winns 255 Sundowner

$20,250

Eustis, Florida

Year 2006

Make Four Winns

Model 255 Sundowner

Category Cuddy Cabin Boats

Length 25

Posted 1 Month Ago

The seller reports everything is in good working order with no known issues. The engine hours are unknown. The seller is the original owner. Make an offer today, this 2006 Four Winns 255 Sundowner is waiting for your next day or overnight on the water! Stock #305086 ALL AROUND GREAT CONDITION!!! 320HP VOLVO PENTA!!! TRAILER INCLUDED!!! Are you ready to hit the water in a family friendly cabin cruiser that's easy to trailer? This 2006 Four Winns 255 Sundowner with a 8'6" beam is exactly what you've been looking for. Bring everyone along for the day, this is rated for 12 passengers with wraparound seating in the cockpit. There's also plenty of storage along with a large swim platform. The comfortable cabin is the perfect place to escape from the elements with a Vee berth, and an enclosed head. Powered by a 5.7 L Volvo Penta GXi engine with a top speed of about 45 MPH. A tandem axle trailer is included with the boat. Reason for selling is no time to enjoy.

1992 Four Winns 205 Sundowner

$11,750

Hanford, California

Year 1992

Make Four Winns

Model 205 Sundowner

Category Cuddy Cabin Boats

Length 20

Posted 1 Month Ago

1992 Four Winns 205 Sundowner appeared to be in good operating condition and there was no damage to the boat that was evident. All systems were said to be operational. Stock #250029 Excellent condition 205 Sundowner! Extras included! Ready to hit the water and cruise! This is a 1992 Four Winns 205 Sundowner powered by a 5.7L V8 producing 270 horsepower. This is a good boat for all-around fun or for those who like to fish. Also included is a full enclosure to give you protection from the elements and it's 18 months old and looks brand new. Also included is a bimini top. New hatch up front, new Humminbird electronics for fishing and navigation, as well as a new stereo. The cuddy cabin can sleep two comfortably and you can sleep two people on the deck as well. Full passenger capacity is 10. This boat is ready to hit the water today and it's priced exceptionally well. Don't wait, call us today! Reason for selling is unable to use anymore.

1996 Four Winns 245 Sundowner

$16,000

Littleton, Colorado

Year 1996

Make Four Winns

Model 245 Sundowner

Category Cuddy Cabin Boats

Length 24

Posted 1 Month Ago

This vessel has all features functional working well claims the seller. Boat has been maintained and winterized by local dealer to help maintain its engine. The deck feels firm and strong without any indication of any soft spots. The vinyl on the vessel shows its age in certain areas. Stock #353643 Four Winn 245 Sundowner Introducing the 1996 Four Winns 245 Sundowner: Are you ready to embark on your next boating adventure? Look no further than the Four Winns 245 Sundowner. This sleek and stylish giant cuddy boat offers a perfect blend of power, performance, and interior comfort. One of the standout features of this remarkable boat is its powerful Volvo Penta engine, paired with a duo prop outdrive. Whether you're cruising along calm waters or exploring more challenging conditions, this combination ensures enhanced maneuverability and exceptional performance, giving you the confidence to handle any situation easily. Its long-term freshwater history sets the Four Winns 245 Sundowner apart from the rest. This means that the vessel, as the seller says, it has been well cared for and used exclusively in freshwater environments by them. Another impressive aspect of this vessel is its low hours for its vintage. Step aboard the 1996 Four Winns 245 Sundowner, and you'll find a larger than average comfortable interior that truly stands the test of time. The spacious cabin allows for overnight stays, accommodating up to four people. The well-appointed forward berth provides a cozy and inviting retreat after a day of adventure. Outside, the Four Winns 245 Sundowner boasts a spacious cockpit area with generous seating for all your guests. The wraparound lounge seating and adjustable captain's chair ensure everyone can relax and enjoy the breathtaking views. The cockpit features a wet bar, perfect for entertaining and keeping refreshments close at hand. This 1996 Four Winns 245 Sundowner with its Volvo Penta engine, duo prop outdrive, long-term freshwater history, and low hours, this vessel is sure to impress even the most discerning boating enthusiast. Reason for selling is not using enough.

2005 Four Winns 205 Sundowner

$19,500

Phoenix, Arizona

Year 2005

Make Four Winns

Model 205 Sundowner

Category Cuddy Cabin Boats

Length 20

Posted 1 Month Ago

According to the seller, This Four Winns Sundowner is in outstanding condition inside and out. There were no signs of dents, dings or scratches to the hull. All systems and equipment operate as designed according to the seller. Stock #375841 205 Sundowner powered by a Mercruiser stern drive engine! This is a tremendous opportunity to purchase this 2005 Four Winns Sundowner in outstanding condition. This Sundowner is pushed by the powerful Mercruiser engine with an Alpha One stern drive. This Sundowner is a great family boat and seats 9 comfortably. It has a V-berth that can sleep 2 and has a porta-potty. This Sundowner is perfect for family fun including skiing, tubing, wakeboarding or just cruising the lake. Don't miss this great opportunity to get this Four Winns Sundowner at a very good price. Please call, email or text with questions or to make an offer. Reason for selling is not using as much anymore.

2006 Four Winns 255 Sundowner

$20,250

Eustis, Florida

Year 2006

Make Four Winns

Model 255 Sundowner

Category Cuddy Cabin Boats

Length 25

Posted 1 Month Ago

The seller reports everything is in good working order with no known issues. The engine hours are unknown. The seller is the original owner. Make an offer today, this 2006 Four Winns 255 Sundowner is waiting for your next day or overnight on the water! Stock #305086 ALL AROUND GREAT CONDITION!!! 320HP VOLVO PENTA!!! TRAILER INCLUDED!!! Are you ready to hit the water in a family friendly cabin cruiser that's easy to trailer? This 2006 Four Winns 255 Sundowner with a 8'6" beam is exactly what you've been looking for. Bring everyone along for the day, this is rated for 12 passengers with wraparound seating in the cockpit. There's also plenty of storage along with a large swim platform. The comfortable cabin is the perfect place to escape from the elements with a Vee berth, and an enclosed head. Powered by a 5.7 L Volvo Penta GXi engine with a top speed of about 45 MPH. A tandem axle trailer is included with the boat. Reason for selling is no time to enjoy.

1991 Four Winns 257 Quest

$29,900

Worcester, Massachusetts

Year 1991

Make Four Winns

Model 257 Quest

Category Walkarounds

Length 25

Posted 1 Month Ago

This great walkaround looks and runs years younger than its age. It offers a recently installed VHF and AM/FFM radio. She has recently undergone a professional stripping and repainting. The cabin is odor-free and in good condition. Don't miss the chance to grab a solid walkaround of this size for under $30k Stock #298961 Check Out This Four Winns Quest Cuddy Cabin Under $30K - Fresh Paint and Many Updates, Ready To Go As far as offshore fishing is concerned, the Four Winns Quest 257 may be one of the best instruments available. Featuring a broad beam and a deep and open cockpit, this Walkaround Cuddy offers generous space and enormous under-floor storage area. Add to that a large rigging locker, port and starboard fish boxes with pump-out and it gives this boat everything you need for an enjoyable and productive day on the water. Powered by twin 150 Johnson engines, the boat has an integral fuel tank capacity of 250 gallons, which allows for an extended range of operation. A canvas enclosure offers protection from the rain, and the cabin has a V-berth that sleeps two comfortably and a full stand-up head. Reason for selling is no longer use it.

1991 Four Winns 257 Quest

$29,900

Worcester, Massachusetts

Year 1991

Make Four Winns

Model 257 Quest

Category Walkarounds

Length 25

Posted 1 Month Ago

This great walkaround looks and runs years younger than its age. It offers a recently installed VHF and AM/FFM radio. She has recently undergone a professional stripping and repainting. The cabin is odor-free and in good condition. Don't miss the chance to grab a solid walkaround of this size for under $30k Stock #298961 Check Out This Four Winns Quest Cuddy Cabin Under $30K - Fresh Paint and Many Updates, Ready To Go As far as offshore fishing is concerned, the Four Winns Quest 257 may be one of the best instruments available. Featuring a broad beam and a deep and open cockpit, this Walkaround Cuddy offers generous space and enormous under-floor storage area. Add to that a large rigging locker, port and starboard fish boxes with pump-out and it gives this boat everything you need for an enjoyable and productive day on the water. Powered by twin 150 Johnson engines, the boat has an integral fuel tank capacity of 250 gallons, which allows for an extended range of operation. A canvas enclosure offers protection from the rain, and the cabin has a V-berth that sleeps two comfortably and a full stand-up head. Reason for selling is no longer use it.

1988 Four Winns 205 Sundowner Cuddy Cabin

$5,995

Orion Charter Township, Michigan

Year 1988

Make Four Winns

Model 205 Sundowner Cuddy Cabin

Category Cuddy Cabin Boats

Length 20'

Posted Over 1 Month

1988 Four Winns 205 Sundowner Cuddy Cabin 1988 Fourwinns Cuddy Cabin, 205 Sundowner with trailer - Very Good Condition

1999 Four Winns Cuddy Cabin 225 Sundowner

$6,499

Brookfield, Connecticut

Year 1999

Make Four Winns

Model Cuddy Cabin 225 Sundowner

Category Powerboats

Length 22'

Posted Over 1 Month

1999 Four Winns Cuddy Cabin 225 Sundowner, This boat is equipped with: - Cockpit Filler Cushions - Table - Porta Potti - Cockpit Cover - Bimini Top - 1999 Tandem Axle Trailer This boat is being sold as is. Our technicians have recently gone through the boat and provided us with the following list of items that should be brought up to a potential customer: - Cracks by ski ring and on platform - Needs bellows - Trim cylinders are leaking - Some upholstery is dry rotted, stained and/or has tears - Some seat bases are rotted - Seat pedistals are very corroded - Steering cylindar is leaking - Right rear speaker doesn't work - Trim sender isn't working properly - Paddle Wheel is broken off - Right trailer fender is bent/dented - Trailer brakes need to be replaced - Master cylinder is dry and rusted - Trailer has drum brakes, we recommend converting them to disc brakes - Starter is not working (the flywheel may also be bad)

21' Four Winns Cuddy Cabin - 1989 - $7500

$7,500

Port St Joe, Florida

Year 1989

Make Four Winns

Model -

Category Cuddy Cabin Boats

Length 21'

Posted Over 1 Month

This boat has been "barn stored" and is in excellent condition. It is all original with a 5.0 liter inboard/outboard motor, possibly the best combination of engine and out drive for this size boat. There are approx. 280 hrs. on the engine, only 30 hrs. in salt water. Engine runs like a sewing machine, with new shift cables, transom boot, and out drive service last fall. Trailer is 2010 Float-On aluminum for easy unload/load. Boat is currently in Northwest Florida (Panhandle). Moving - must sell!