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22 used pickup trucks for sale in Milwaukee, WI

White 2016 Nissan Frontier S for sale in Milwaukee, WIPhotos of 2016 Nissan Frontier S for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2016 Nissan Frontier S for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2016 Nissan Frontier S at Diamond Jim's Motor Cars, WIMore photos of 2016 Nissan Frontier S at Diamond Jim's Motor Cars, WI
Stock # 737775
S
160,631 miles
$6,997
Blue 2019 Ford Ranger XLT for sale in Milwaukee, WIPhotos of 2019 Ford Ranger XLT for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2019 Ford Ranger XLT for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2019 Ford Ranger XLT at Diamond Jim's Motor Cars, WIMore photos of 2019 Ford Ranger XLT at Diamond Jim's Motor Cars, WI
Stock # A66414A
XLT
146,744 miles
was $18,997
$17,997
White 2022 Chevrolet Colorado LT for sale in Milwaukee, WIPhotos of 2022 Chevrolet Colorado LT for sale in Milwaukee, WI at Diamond Jim's West AllisAnother view of 2022 Chevrolet Colorado LT for sale in Milwaukee, WI at Diamond Jim's West AllisMore photos of 2022 Chevrolet Colorado LT at Diamond Jim's West Allis, WIMore photos of 2022 Chevrolet Colorado LT at Diamond Jim's West Allis, WI
Stock # XY124718
was $20,997
$20,000
White 2022 Chevrolet Colorado LT for sale in Milwaukee, WIPhotos of 2022 Chevrolet Colorado LT for sale in Milwaukee, WI at Diamond Jim's West AllisAnother view of 2022 Chevrolet Colorado LT for sale in Milwaukee, WI at Diamond Jim's West AllisMore photos of 2022 Chevrolet Colorado LT at Diamond Jim's West Allis, WIMore photos of 2022 Chevrolet Colorado LT at Diamond Jim's West Allis, WI
Stock # XY124710
was $22,997
$20,000
Gray 2017 Nissan Titan SV for sale in Milwaukee, WIPhotos of 2017 Nissan Titan SV for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2017 Nissan Titan SV for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2017 Nissan Titan SV at Diamond Jim's Motor Cars, WIMore photos of 2017 Nissan Titan SV at Diamond Jim's Motor Cars, WI
Stock # 539783
SV
94,678 miles
$18,997
Black 2019 Ford F-150 XLT for sale in Milwaukee, WIPhotos of 2019 Ford F-150 XLT for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2019 Ford F-150 XLT for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2019 Ford F-150 XLT at Diamond Jim's Motor Cars, WIMore photos of 2019 Ford F-150 XLT at Diamond Jim's Motor Cars, WI
Stock # C52483
XLT
98,756 miles
was $25,000
$23,997
White 2019 Ford F-150 XLT for sale in Milwaukee, WIPhotos of 2019 Ford F-150 XLT for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2019 Ford F-150 XLT for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2019 Ford F-150 XLT at Diamond Jim's Motor Cars, WIMore photos of 2019 Ford F-150 XLT at Diamond Jim's Motor Cars, WI
Stock # C68934
XLT
115,503 miles
was $23,777
$21,777

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White 2006 Chevrolet Silverado 2500HD Work Truck for sale in Milwaukee, WIPhotos of 2006 Chevrolet Silverado 2500HD Work Truck for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2006 Chevrolet Silverado 2500HD Work Truck for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2006 Chevrolet Silverado 2500HD Work Truck at Diamond Jim's Motor Cars, WIMore photos of 2006 Chevrolet Silverado 2500HD Work Truck at Diamond Jim's Motor Cars, WI
Stock # 146219A
Work Truck
47,077 miles
$16,997
Green 2012 Toyota Tundra Grade for sale in Milwaukee, WIPhotos of 2012 Toyota Tundra Grade for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2012 Toyota Tundra Grade for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2012 Toyota Tundra Grade at Diamond Jim's Motor Cars, WIMore photos of 2012 Toyota Tundra Grade at Diamond Jim's Motor Cars, WI
Stock # 038255
Grade
212,500 miles
was $12,997
$11,997
Black 2022 Chevrolet Colorado LT for sale in Milwaukee, WIPhotos of 2022 Chevrolet Colorado LT for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2022 Chevrolet Colorado LT for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2022 Chevrolet Colorado LT at Diamond Jim's Motor Cars, WIMore photos of 2022 Chevrolet Colorado LT at Diamond Jim's Motor Cars, WI
Stock # 213290
$20,997
Green 2003 Ford F-250SD Lariat for sale in Milwaukee, WIPhotos of 2003 Ford F-250SD Lariat for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2003 Ford F-250SD Lariat for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2003 Ford F-250SD Lariat at Diamond Jim's Motor Cars, WIMore photos of 2003 Ford F-250SD Lariat at Diamond Jim's Motor Cars, WI
Stock # B28449
Lariat
66,051 miles
$18,997
Silver 2018 Chevrolet Silverado 1500 LTZ for sale in Milwaukee, WIPhotos of 2018 Chevrolet Silverado 1500 LTZ for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2018 Chevrolet Silverado 1500 LTZ for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2018 Chevrolet Silverado 1500 LTZ at Diamond Jim's Motor Cars, WIMore photos of 2018 Chevrolet Silverado 1500 LTZ at Diamond Jim's Motor Cars, WI
Stock # 503137
$25,000
Black 2013 Chevrolet Avalanche 1500 LT for sale in Milwaukee, WIPhotos of 2013 Chevrolet Avalanche 1500 LT for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2013 Chevrolet Avalanche 1500 LT for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2013 Chevrolet Avalanche 1500 LT at Diamond Jim's Motor Cars, WIMore photos of 2013 Chevrolet Avalanche 1500 LT at Diamond Jim's Motor Cars, WI
Stock # 273752
$15,000

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Black 2021 Jeep Gladiator Overland for sale in Milwaukee, WIPhotos of 2021 Jeep Gladiator Overland for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 2021 Jeep Gladiator Overland for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 2021 Jeep Gladiator Overland at Diamond Jim's Motor Cars, WIMore photos of 2021 Jeep Gladiator Overland at Diamond Jim's Motor Cars, WI
Stock # 583866
Overland
145,737 miles
$25,000
New arrival - photos coming soon
Stock # XYB81100
XL
168,656 miles
$10,000
White 2015 GMC Sierra 3500HD Denali for sale in Milwaukee, WIPhotos of 2015 GMC Sierra 3500HD Denali for sale in Milwaukee, WI at Diamond Jim's West AllisAnother view of 2015 GMC Sierra 3500HD Denali for sale in Milwaukee, WI at Diamond Jim's West AllisMore photos of 2015 GMC Sierra 3500HD Denali at Diamond Jim's West Allis, WIMore photos of 2015 GMC Sierra 3500HD Denali at Diamond Jim's West Allis, WI
Stock # XY588565
Denali
58,816 miles
$42,500
New arrival - photos coming soon
Stock # 217153
Laramie Longhorn
63,949 miles
was $28,997
$25,000
New arrival - photos coming soon
Stock # A74628
King Ranch
198,637 miles
$18,500
New arrival - photos coming soon
Stock # A23080
Platinum
126,521 miles
$30,000

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New arrival - photos coming soon
Stock # 638103A
SLT
120,615 miles
$25,000
Black 1990 Chevrolet C/K 1500 454 SS for sale in Milwaukee, WIPhotos of 1990 Chevrolet C/K 1500 454 SS for sale in Milwaukee, WI at Diamond Jim's Motor CarsAnother view of 1990 Chevrolet C/K 1500 454 SS for sale in Milwaukee, WI at Diamond Jim's Motor CarsMore photos of 1990 Chevrolet C/K 1500 454 SS at Diamond Jim's Motor Cars, WIMore photos of 1990 Chevrolet C/K 1500 454 SS at Diamond Jim's Motor Cars, WI
Stock # 194487
454 SS
50,375 miles
$50,000
New arrival - photos coming soon
Stock # C91569
Lariat
53,151 miles
$31,997
Showing 22 of 22 results

Used trucks for sale in Milwaukee, WI

If you’re searching for dependable and capable used trucks in Milwaukee, Diamond Jim’s offers a strong selection of pre-owned pickup trucks built for work, play, and everything in between. With two convenient Milwaukee locations, finding the right truck for your needs has never been easier.

From light-duty daily drivers to heavy-duty haulers, our used truck inventory includes options designed for power, durability, and long-term value—perfect for Wisconsin roads and job sites.

Popular used truck makes & models

Our used truck inventory regularly features trusted brands and best-selling models, including:

• Ford F-150, F-250 & Ranger – America’s favorite trucks known for towing, technology, and versatility

• Chevrolet Silverado 1500 & Colorado – Proven performance with strong payload and trailering capability

• GMC Sierra 1500 & Canyon – Refined pickups offering power and premium features

• Ram 1500 & 2500 – Smooth-riding trucks with impressive strength and interior comfort

• Toyota Tacoma & Tundra – Legendary reliability with off-road-ready options

• Nissan Frontier & Titan – Capable trucks built for work and weekend adventures

Inventory changes frequently, so check back often to find the right truck for your lifestyle or business.

Why buy a used truck from Diamond Jim’s?

Milwaukee-area truck buyers choose Diamond Jim’s for:

• A wide selection of quality pre-owned trucks

• Competitive pricing and transparent vehicle history

• Options for towing, hauling, construction, and recreation

• Financing solutions for a wide range of credit situations

• A friendly, knowledgeable team focused on your needs

Whether you need a dependable work truck or a versatile pickup for everyday driving, we’re here to help.

Proudly serving Milwaukee & nearby communities

We proudly serve drivers shopping for used trucks near Milwaukee, WI, including:

Milwaukee • West Allis • Wauwatosa • Greenfield • Shorewood • Glendale • Oak Creek • Cudahy • South Milwaukee • Brookfield • Menomonee Falls

With two Milwaukee locations, your next truck is always close by.

Shop used trucks in Milwaukee today

Browse our current used truck inventory online, then visit Diamond Jim’s to schedule a test drive and explore financing options that fit your budget.

Diamond Jim’s — Quality Used Trucks for Sale in Milwaukee, WI

Information deemed reliable, but not guaranteed. Interested parties should confirm all data before relying on it to make a purchase decision. All prices and specifications are subject to change without notice. Prices may not include additional fees such as government fees and taxes, title and registration fees, finance charges, dealer document preparation fees, processing fees, and emission testing and compliance charges.