Boats for sale in Madison Wisconsin - BoatCrazy

599 boats found within 100 miles from Madison, Wisconsin

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2026 Chaparral SSi

$64,995

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 21'
- 2026 / Used
- $64,995
A rare current-model pre-owned opportunity, combining 250 HP performance with a black folding arch, upgraded flooring and a fully equipped helm.Highlights: MerCruiser 4.5L 250 HP... View Details

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$64,995
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2027 Chaparral SSi

$100,455

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 23'
- 2027 / New
- $100,455
Built with a sleek, upscale look and a strong mix of comfort, convenience and performance upgrades, this Chaparral stands out with its solid black hull, Cayenne interior and black... View Details

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$100,455
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2026 Tidewater LXF

$179,995

Oshkosh, WI
- Oshkosh, WI
- Fishing Center Console
- 25'
- 2026 / New
- $179,995
Big-water capability meets upscale family comfort, with twin Racing outboards, a glass-cockpit helm and thoughtful amenities from bow to stern.Highlights: Twin Mercury 150R Racing... View Details

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$179,995
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2027 Chaparral SSi

$86,575

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 23'
- 2027 / New
- $86,575
A sharp, well-equipped bowrider with an all-black exterior, Cayenne interior and the comfort upgrades that make long days on the water even better. Highlights: Mercury MPI Sterndri... View Details

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$86,575
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2027 Godfrey AP 255 SBC

$149,995

Oshkosh, WI
- Oshkosh, WI
- Pontoon
- 0'
- 2027 / New
- $149,995
A premium AquaPatio built with a strong mix of performance, comfort and entertaining upgrades. This configuration stands out with its upgraded iMPACT center tube package, Mercury V... View Details

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$149,995
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2027 Chaparral SSi

$77,350

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 21'
- 2027 / New
- $77,350
A sharp, well-equipped bowrider finished in full Island Green gelcoat with a premium Dune interior and a white folding arch tower. Highlights: Mercury MPI Sterndrive with Alpha Dri... View Details

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$77,350
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2026 Chaparral SSi

$87,195

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 23'
- 2026 / New
- $87,195
Roomy, family-friendly bowrider with plenty of seating, strong V6 power and the features you want for full days on the water.Highlights: MerCruiser 4.5L 250 HP Simrad NSX9 Touchsc... View Details

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$87,195
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2027 Chaparral SSi

$75,650

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 21'
- 2027 / New
- $75,650
A striking, feature-rich Chaparral bowrider finished in a solid black hull with Cayenne interior and loaded with some of the most desirable upgrades available. Highlights: Mercury... View Details

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$75,650
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2020 Bayliner VR Series

$29,995

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 22'
- 2020 / Used
- $29,995
A spacious, easygoing bowrider that gives families more room to stretch out without stepping up to a much larger boat.Highlights: MerCruiser 4.5L 200 HP BeamForward Design Seatin... View Details

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$29,995
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2022 Chaparral SSX

$149,995

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 28'
- 2022 / Used
- $149,995
Low-hour luxury bowrider with big-block V8 power, premium upgrades and plenty of room for cruising and entertaining.Highlights: 380 HP MerCruiser 8.2L DTS Only 59 Hours EFX Elect... View Details

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$149,995
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2026 Godfrey 235 SFLC

$64,995

Oshkosh, WI
- Oshkosh, WI
- Pontoon
- 0'
- 2026 / Used
- $64,995
A refined tritoon built around comfort, bold styling and strong 200 HP performance for relaxed cruising and entertaining.Highlights: Mercury 200L Pro XS Simrad Chartplotter/Fish F... View Details

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$64,995
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Price Drop
2027 Sweetwater 2286 SFLC

$72,995

Oshkosh, WI
- Oshkosh, WI
- Pontoon
- 0'
- 2027 / New
- $72,995
NEW 2027 Godfrey Sweetwater 2286 SFLCThe 2027 Godfrey Sweetwater 2286 SFLC blends the easygoing comfort the Sweetwater lineup is known for with a versatile lounge-focused layout a... View Details

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$72,995
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2027 Chaparral SSi

$90,925

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 23'
- 2027 / New
- $90,925
Island Green styling, a black folding arch and a comfort-focused cockpit give this SSi a look that stands out before you ever leave the dock. Highlights: Island Green Hull Sides B... View Details

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$90,925
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2006 Monterey 282 Cruiser

$54,995

Oshkosh, WI
- Oshkosh, WI
- Cruiser
- 0'
- 2006 / Used
- $54,995
A true weekend cruiser with overnight accommodations, a full galley and plenty of cockpit space for entertaining on the water.Highlights: Twin MerCruiser 4.3L Sterndrives 440 HP T... View Details

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$54,995
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2020 Chaparral SSX

$56,995

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 23'
- 2020 / Used
- $56,995
A premium bowrider that gives you the upscale feel of a larger boat without sacrificing the sporty, easy-to-enjoy layout that makes a Chaparral so versatile. Premium Chaparral comf... View Details

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$56,995
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2006 Rinker 360 Fiesta Vee

$79,995

Oshkosh, WI
- Oshkosh, WI
- Cruiser
- 0'
- 2006 / Used
- $79,995
Big-Block Power, Spacious Overnight Accommodations & a Cockpit Built for Entertaining This 2006 Rinker 360 Fiesta Vee is a substantial express cruiser that offers the space and ame... View Details

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$79,995
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2026 Tidewater CC Adventure

$79,995

Oshkosh, WI
- Oshkosh, WI
- Fishing Center Console
- 20'
- 2026 / New
- $79,995
A true do-it-all center console with the space to fish hard, cruise comfortably and handle choppier water with confidence.Highlights: Mercury 200 XL FourStroke Garmin GPSMAP 943xs... View Details

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$79,995
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2026 Other 895 DC

$83,253

Oshkosh, WI
- Oshkosh, WI
- Fishing Bass Boat
- 0'
- 2026 / New
- $83,253
Dialed in for serious freshwater fishing, with a high-end electronics package, tournament-ready trolling motor and comfort upgrades for long days behind the wheel.Highlights: Mercu... View Details

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$83,253
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2027 Chaparral OSX

$391,445

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 30'
- 2027 / New
- $391,445
A premium new-model bowrider loaded with standout upgrades, combining Chaparrals upscale SSX styling with strong Mercury performance and a well-appointed cockpit. Highlights: 300 H... View Details

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$391,445
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2027 Chaparral SSi

$74,775

Oshkosh, WI
- Oshkosh, WI
- Bowrider
- 21'
- 2027 / New
- $74,775
The Seafoam Green and black color combination gives this SSi a look that stands apart, while a folding arch, extended swim platform and upgraded SeaDek make it equally ready for cr... View Details

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$74,775
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Price Drop
2027 Sweetwater 2286 SFLC

$64,995

Oshkosh, WI
- Oshkosh, WI
- Pontoon
- 0'
- 2027 / New
- $64,995
NEW 2027 Godfrey Sweetwater 2286 SFLCThe 2027 Godfrey Sweetwater 2286 SFLC is built for the way most families actually use a pontoon: cruising, relaxing, entertaining, swimming, a... View Details

View 34 Photos and Details Contact Seller

$64,995
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Showing 316 to 336 of 599 boats found.

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