Boats for sale in Chicago Illinois

1,633 boats found within 100 miles out of 14,252 Boats Found

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1999 Sea Ray 500 Sundancer

$199,000

South Haven, MI
- South Haven, MI
- Express Cruiser
- 50'
- 1999 / Used
- $199,000
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

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$199,000
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2023 Custom Built 25 Hadlee Houseboat

$69,000

South Haven, MI
- South Haven, MI
- Houseboat
- 25'
- 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

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$69,000
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2021 Sylvan L3 LZ

$38,700

Edwardsburg, MI
- Edwardsburg, MI
- Pontoon
- 24'
- 2021 / Used
- $38,700
Stock #452780 Video of this vessel available at www [dot] popsells [dot] com/view/452780 Reason for selling is "Doesn't use it. Came with the home.". ANY and ALL offers will be... View Details

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$38,700
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2025 Mastercraft XSTAR

$354,977

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23'
- 2025 / New
- $354,977
Act fast on this limited-time offer! Experience Unmatched Performance Introducing the 2025 Mastercraft XSTAR, where cutting-edge engineering meets exhilarating performance. This st... View Details

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$354,977
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2025 Mastercraft NXT22

$128,525

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22'
- 2025 / New
- $128,525
Contact us to find out ALL available savings! The fresh new MasterCraft NXT22 is big news. One of our most popular boats ever has a brand new design and updates from tip to tail. T... View Details

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$128,525
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Price Drop
2025 Sea Ray SDX 270

$182,584

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 27'
- 2025 / New
- $182,584
Contact us to find out ALL available savings! Act fast on this limited-time offer! The SDX 270 delivers on maximum capability to make a full day on the water easy to enjoy. With pl... View Details

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$182,584
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2025 Barletta LUSSO23UC

$113,317

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2025 / New
- $113,317
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UC Is Lusso right for you? Designed with you, and your on-water experience, in mind, the Barletta Lusso models offer... View Details

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$113,317
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2014 Starcraft 2000 LIMITED

$21,995

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 20'
- 2014 / Used
- $21,995
The 2014 Starcraft 2000 LIMITED is a versatile and well-equipped deck boat designed for a wide range of recreational activities on the water. Combining stylish aesthetics with robu... View Details

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$21,995
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2005 Sea Ray 320 SUNDANCER

$89,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 35'
- 2005 / Used
- $89,995
well maintained two owner boat that has been exclusively used on Lake Michigan. Always stored in a heated building during the off-season. Features of this boat include radar, chart... View Details

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$89,995
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2026 Starcraft SV 18 OB

$42,278

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 18'
- 2026 / New
- $42,278
Act fast on this limited-time offer! 2026 Starcraft 18SVOB: A New Frontier in Luxury Boating Discover the thrill of the open water with the 2026 Starcraft 18SVOB, a stunning blend... View Details

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$42,278
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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 D20

$47,447

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 20'
- 2025 / New
- $47,447
Contact us to find out ALL available savings! Act fast on this limited-time offer! The D20 outboard model is perfect for families looking for versatility and comfort on the water.... View Details

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$47,447
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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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2026 Starcraft EX 20 FD

Call for price

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20'
- 2026 / New
- Call for price
2026 Starcraft EX 20 FD Embrace the open waters with the 2026 Starcraft EX 20 FD, a luxurious vessel designed for adventure and relaxation. The elegant lines of this boat are compl... View Details

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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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2017 Godfrey SWEETWATER 2486 SB

$36,900

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 24'
- 2017 / Used
- $36,900
2017 Godfrey SWEETWATER 2486 SB View Details

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$36,900
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2017 Robalo R302

$144,900

Pewaukee, WI
- Pewaukee, WI
- Fishing Center Console
- 30'
- 2017 / Used
- $144,900
2017 Robalo 302 Center Console, LOADED!! Turn heads at the dock and dominate the water in this exceptionally equipped 2017 302 Center Console. Plwered by T-Yamaha 300HP Outboard, t... View Details

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$144,900
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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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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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2025 Harris Cruiser 210

Call for price

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 24'
- 2025 / New
- Call for price
Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line. No matter what you decide, the Cruiser has the amenities to make t... View Details

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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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