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There are 2160 new and used boats for sale in Winthrop Harbor, Illinois. Browse Outboard Motors, Pontoon, Fishing, Center Console, Cruiser, and Runabout from brands like Scout, Mercury, Yamaha, Sea Ray, Honda, and Harris on BoatCrazy. View a wide selection of boats from $300 to $3,890,000.
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  • Boats
  • Within 100 Miles Of
    Winthrop Harbor, Illinois
2,160 boats found within 100 miles from Winthrop Harbor, Illinois
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  • 2021 Chaparral 307 SSX

    2021 Chaparral 307 SSX

    $149,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 30' / 9'
    • 2021 / Used
    • $149,900

    One-Owner, Fresh-Water, rack-stored Chaparral 307 SSX. Plushness and Performance! Loaded with all of Chaparral's best features, with an abundance of passenger space, the 307 SSX is... View Details

    View 39 Photos and Details Contact Seller
    $149,900
    VIEW DETAILS
  • 2024 Cobalt R8 Outboard

    2024 Cobalt R8 Outboard

    $219,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 27' / 8'
    • 2024 / Used
    • $219,900

    See This stunning 2024 Cobalt R8 Outboard, a remarkable bowrider that combines elegance with performance. Measuring an impressive 27.83 feet in overall length, this vessel is craft... View Details

    View 48 Photos and Details Contact Seller
    $219,900
    VIEW DETAILS
  • 2007 Chaparral 350 Signature

    2007 Chaparral 350 Signature

    $129,500
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 37' / 11'
    • 2007 / Used
    • $129,500

    Always fresh-water, loaded with features. Twin Merc 8.1L 370 HP inboards with 460 hours. This is an ideal opportunity to own a well-cared-for Chaparral 350 Signature featuring a pr... View Details

    View 35 Photos and Details Contact Seller
    $129,500
    VIEW DETAILS
  • 2005 Formula 260 Bowrider

    2005 Formula 260 Bowrider

    $46,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Runabout
    • 26' / 8'
    • 2005 / Used
    • $46,900

    Chase sunsets with this 2005 Formula 260 Bowrider, a premium sport boat built for performance, comfort, and luxury. A top brand known for its superior handling, quality constructio... View Details

    View 31 Photos and Details Contact Seller
    $46,900
    VIEW DETAILS
  • Price Drop 2018 Chaparral Vortex 203 VRX

    2018 Chaparral Vortex 203 VRX

    $32,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Jet boat
    • 20' / 8'
    • 2018 / Used
    • $32,900

    The 203 VRX features the hull design, interior layout and high quality construction Chaparral is known for. In addition to the head-turning style, the VRX includes a black folding... View Details

    View 42 Photos and Details Contact Seller
    $32,900
    VIEW DETAILS
  • 2000 Crownline 290 CR

    2000 Crownline 290 CR

    $34,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 31' / 10'
    • 2000 / Used
    • $34,900

    This Crownline 290 CR is a spacious small express cruiser powered by twin Mercruiser 5.7 EFI's and NEW Bravo III drives! She has about 700 hours on her hour meters and appears to h... View Details

    View 30 Photos and Details Contact Seller
    $34,900
    VIEW DETAILS
  • Price Drop 2021 Qwest LS 822 DS Bar

    2021 Qwest LS 822 DS Bar

    $49,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Pontoon
    • 22' / 8'
    • 2021 / Used
    • $49,900

    This 2021 Qwest LS 822 perfectly blends style and performance with great fishing capabilites. Power by a 200HP Honda and Upgraded tiple toon package and aluminum underskining makes... View Details

    View 34 Photos and Details Contact Seller
    $49,900
    VIEW DETAILS
  • Price Drop 2017 Chaparral 330 Signature

    2017 Chaparral 330 Signature

    $194,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 33' / 10'
    • 2017 / Used
    • $194,900

    Now available, see this 2017 Chaparral 330 Signature. Always fresh-water, with just 243 engine hours. Designed for summer adventures and weekend getaways, the Chaparral 330 Signatu... View Details

    View 51 Photos and Details Contact Seller
    $194,900
    VIEW DETAILS
  • Price Drop 2016 Chaparral 307 SSX

    2016 Chaparral 307 SSX

    $129,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 30' / 9'
    • 2016 / Used
    • $129,900

    Meet your next on-the-water obsession: the 2016 Chaparral 307 SSX  a head turning mix of luxury, performance, and pure boating bliss! At 30 feet, she delivers a ride as smooth as s... View Details

    View 48 Photos and Details Contact Seller
    $129,900
    VIEW DETAILS
  • Price Drop 2000 Chaparral Signature 300

    2000 Chaparral Signature 300

    $37,500
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 29' / 10'
    • 2000 / Used
    • $37,500

    If you are looking for a small family cruiser with all the amenities you just found it! This Chaparral Signature 300 has all the creature comforts including Air Conditioning, Fusio... View Details

    View 31 Photos and Details Contact Seller
    $37,500
    VIEW DETAILS
  • 2002 Maxum 2700 SCR

    2002 Maxum 2700 SCR

    $32,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Cruiser
    • 28' / 0'
    • 2002 / Used
    • $32,900

    This one-owner 2002 Maxum 2700 SCR has spent its life on the fresh waters of Southwest Michigan and shows the care you hope to find in a well-kept family cruiser. With sleek stylin... View Details

    View 49 Photos and Details Contact Seller
    $32,900
    VIEW DETAILS
  • 2006 Chaparral 310 Signature

    2006 Chaparral 310 Signature

    $64,900
    Saint Joseph, MI

    This 2006 Chaparral 310 Signature is a sleek and luxurious cruiser designed for thosewho appreciate both performance and comfort on the water. With a length overall of 33 feet and... View Details

    View 35 Photos and Details Contact Seller
    $64,900
    VIEW DETAILS
  • 1999 Trojan 360 Express

    1999 Trojan 360 Express

    $68,900
    Saint Joseph, MI

    Spacious and Sporty, this Trojan (by Carver) 360 Express is the perfect family boat for cruising and enjoying the water! It is equipped with a Kohler generator for those hot summer... View Details

    View 32 Photos and Details Contact Seller
    $68,900
    VIEW DETAILS
  • 1998 Cherokee 270 Sportsman

    1998 Cherokee 270 Sportsman

    $24,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Pilothouse
    • 27' / 0'
    • 1998 / Used
    • $24,900

    Step aboard a piece of Great Lakes craftsmanship—this 1998 Cherokee 270 Sportsman is the kind of boat that rarely hits the market. Built right here in Michigan, the Cherokee line... View Details

    View 53 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • 2002 Regal 3860

    2002 Regal 3860

    $109,000
    Saint Joseph, MI

    Stock #467673 Reason for selling is "New Adventure!". This Regal has recently been added to market (May 1st). Submit your offer today! Incredible luxury, performance, and a soun... View Details

    View 10 Photos and Details Contact Seller
    $109,000
    VIEW DETAILS
  • 1995 Gibson 44 Classic

    1995 Gibson 44 Classic

    $79,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Houseboat
    • 44' / 0'
    • 1995 / Used
    • $79,900

    See this well-loved and well-cared-for Gibson 44. "Lou's Yourself" has always been boated in fresh water, is beautifully decored and loaded with accessories. Twin Crusader 454's, W... View Details

    View 74 Photos and Details Contact Seller
    $79,900
    VIEW DETAILS
  • 2022 Other 22QL

    2022 Other 22QL

    $29,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Pontoon
    • 22' / 0'
    • 2022 / Used
    • $29,900

    Hit the water now with this 2022 Nepallo 22QL tritoon, the perfect blend of performance, comfort, and style. Powered with a 115HP Suzuki for smooth cruising and equipped with a tri... View Details

    View 23 Photos and Details Contact Seller
    $29,900
    VIEW DETAILS
  • 2017 Scout 225 XSF

    2017 Scout 225 XSF

    $64,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Fishing
    • 22' / 0'
    • 2017 / Used
    • $64,900

    Turn heads on the water with this clean 2017 Scout 225 XSF, a premium bay/near-shore center console known for its blend of performance, fishability, and family comfort. This Scout... View Details

    View 39 Photos and Details Contact Seller
    $64,900
    VIEW DETAILS
  • 1999 Sea Ray 500 Sundancer

    1999 Sea Ray 500 Sundancer

    $199,000
    South Haven, MI

    Stock #471094 Video of this vessel available at www [dot] popsells [dot] com/view/471094 Reason for selling is "Has not used enough". ANY and ALL offers will be put in front of... View Details

    View 10 Photos and Details Contact Seller
    $199,000
    VIEW DETAILS
  • 2023 Custom Built 25 Hadlee Houseboat

    2023 Custom Built 25 Hadlee Houseboat

    $69,000
    South Haven, MI
    • South Haven, MI
    • Houseboat
    • 25' / 8'
    • 2023 / Used
    • $69,000

    Custom Built Houseboat Immerse yourself in stylish and comfortable houseboat living with this newly built 2023 Hadley Houseboat, only the third one built, the other two have b... View Details

    View 25 Photos and Details Contact Seller
    $69,000
    VIEW DETAILS
  • 1994 Rinker 190 CAPTIVA (175 HP MCM)

    1994 Rinker 190 CAPTIVA (175 HP MCM)

    $1,496
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 19' / 8'
    • 1994 / Used
    • $1,496

    ️ 1994 Rinker 190 Captiva – Affordable Bowrider Opportunity Turn heads on the water with this classic 19-foot Rinker Captiva—an ideal platform for restoration or repower. With its... View Details

    View 12 Photos and Details Contact Seller
    $1,496
    VIEW DETAILS
Showing 1618 to 1638 of 2,160 boats found.
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