Boats for sale in Chicago Illinois

1,161 boats found within 100 miles out of 13,655 Boats Found

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2026 Bayliner E16LE

$26,633

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 16'
- 2026 / New
- $26,633
Act fast on this limited-time offer! Experience Elegance on Water Introducing the stunning 2026 Bayliner E16LE, a luxurious vessel that redefines your aquatic adventures. Nestled a... View Details

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$26,633
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2026 Starcraft GX 18 R

$30,214

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 18'
- 2026 / New
- $30,214
Act fast on this limited-time offer! The Starcraft Pontoon GX 18 R offers a perfect blend of style and functionality, making it an ideal choice for water enthusiasts. Built on robu... View Details

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$30,214
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2025 Bayliner V20I

$51,501

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 20'
- 2025 / New
- $51,501
Contact us to find out ALL available savings! Act fast on this limited-time offer! 2025 Bayliner V20I Experience the pinnacle of luxury boating with the exquisite 2025 Bayliner V20... View Details

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$51,501
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2026 Barletta Cabrio 22 QC

$89,436

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $89,436
Act fast on this limited-time offer! 2026 Barletta CABRIO22QC Step into the world of luxury and performance with the stunning 2026 Barletta CABRIO22QC. Crafted with precision, this... View Details

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$89,436
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2026 Barletta Cabrio 22 UC

$86,877

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $86,877
Is the Cabrio right for you? Spend time with family on the water in the price concious Cabrio. The same fit and finish, innovation, performance and superior construction that Barle... View Details

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$86,877
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2027 Starcraft EX 20 Q DH

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20'
- 2027 / New
- Call for price
The Starcraft EX 20 Q DH pontoon boat offers the perfect blend of relaxation and versatility for creating lasting memories on the water. Up front, plush lounges provide a comfortab... View Details

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2026 Barletta Cabrio 22 QC

$84,068

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $84,068
Act fast on this limited-time offer! Experience Luxury on Water Introducing the 2026 Barletta CABRIO22QC, a stunning embodiment of craftsmanship and performance that will elevate y... View Details

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$84,068
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2026 Barletta Cabrio 22 UC

$86,500

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $86,500
Act fast on this limited-time offer! 2026 Barletta CABRIO22UC Experience the ultimate in luxury and performance with the stunning 2026 Barletta CABRIO22UC. Nestled in the picturesq... View Details

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$86,500
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2027 Starcraft VX 20 R DH

Call for price

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20'
- 2027 / New
- Call for price
Experience the Waters Like Never Before Introducing the stunning 2026 Starcraft VX 20 R DH, available exclusively at SkipperBud's Pewaukee in Pewaukee, WI. Immerse yourself in a wo... View Details

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2022 Bayliner VR5 Bowrider I/O

$35,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 20'
- 2022 / Used
- $35,995
2022 Bayliner VR5 Bowrider I/O View Details

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$35,995
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2018 Sea Ray 350 SUNDANCER

$279,495

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 35'
- 2018 / Used
- $279,495
🌊 ONE OWNER • FRESHWATER ONLY • UNDER 300 HOURS • LOADED WITH OPTIONS • IMPECCABLY MAINTAINED 🌊 Opportunity Knocks! This exceptional Sea Ray 350 Sundancer is the kind of boat dis... View Details

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$279,495
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1996 Sea Ray 270 SUNDANCER

$9,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 29'
- 1996 / Used
- $9,995
Introducing the 1996 Sea Ray 270 Sundancer - Where Luxury Meets Adventure. Experience the epitome of boating elegance with our meticulously crafted vessel, designed for those who d... View Details

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$9,995
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2004 Starcraft ELITE 226

$14,864

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25'
- 2004 / Used
- $14,864
Step aboard the 2004 Starcraft ELITE 226 and experience Pewaukee’s lake life in comfort and style. Powered by a reliable Mercury 50HP outboard engine and supported by an advanced h... View Details

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$14,864
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2019 Sea Ray 280 SLX

$149,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 28'
- 2019 / Used
- $149,995
2019 Sea Ray 280 SLX Turn heads and make every day on the water unforgettable with this exceptionally well-kept 2019 Sea Ray 280 SLX. Owned by just two owners since new, this premi... View Details

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$149,995
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1998 Cruisers 3585

$69,995

Pewaukee, WI
- Pewaukee, WI
- Yacht
- 35'
- 1998 / Used
- $69,995
Experience big-water cruising without the big-water price tag aboard this well-maintained 1998 Cruisers 3585 Express Bridge. Powered by dependable twin 7.4L MPI V-Drive inboards, t... View Details

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$69,995
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1998 Silverton 351

$64,995

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 38'
- 1998 / Used
- $64,995
1998 Silverton 351 Sedan Bridge – Exceptional Condition, Incredible Value! If you’ve been searching for a spacious, comfortable cruising yacht that delivers big-boat amenities with... View Details

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$64,995
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2004 Carver 396 MY

$154,995

Pewaukee, WI
- Pewaukee, WI
- Yacht
- 39'
- 2004 / Used
- $154,995
This exceptionally well-maintained 2004 Carver 396 Motor Yacht is a true reflection of pride of ownership and an opportunity that discerning buyers will not want to miss. Powered... View Details

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$154,995
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2025 Apex A 24

$124,900

Pewaukee, WI
- Pewaukee, WI
- Rigid Inflatable
- 24'
- 2025 / Used
- $124,900
A24 RIB 🔥 Powered by twin Mercury 115HP outboards and loaded with premium upgrades including an optional hardtop, Radar, GPS/Chart Plotter, and upgraded upholstery, this Apex A24... View Details

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$124,900
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2023 Bayliner VR6 Bowrider

$49,995

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 22'
- 2023 / Used
- $49,995
A larger version of our new VR5, the VR6 is also all about space and unparalleled roominess. It combines Bayliner’s category-leading BeamForward™ design and new AftAdvantage™ conce... View Details

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$49,995
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2002 Sea Ray 220 SUNDECK

$14,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 23'
- 2002 / Used
- $14,995
2002 Sea Ray 220 SUNDECK View Details

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$14,995
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2021 Cruisers 38 GLS

$449,000

Pewaukee, WI
- Pewaukee, WI
- Yacht
- 38'
- 2021 / Used
- $449,000
This 2021 Cruisers Yachts 38 GLS offers a rare combination of luxury, performance, and true exclusivity. Powered by a highly sought-after triple Mercury 450R Racing outboard packag... View Details

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$449,000
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