CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Iron Ridge, WI

129 results
Iron Ridge, WI
2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Jon Green Family Auto

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

36,980 miles

$32,979

Fair Deal
Milton, WI
47 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
36,980
Stock number:
1968A
VIN:
1GCRYCEF6LZ361683

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

119,478 miles

$25,991

Good Deal
Chilton, WI
48 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
119,478
Stock number:
14801A1
VIN:
1GCPYCEF0MZ378830

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

61,218 miles

$35,209

Fair Deal
West Bend, WI
16 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
61,218
Stock number:
WPU472A
VIN:
1GCPYCEL1NZ125782

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,881 miles

$29,497

Good Deal
Sheboygan, WI
44 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior color:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
65,881
Stock number:
D414867T
VIN:
1GCPYCEH5MZ383894

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

119,478 miles

$25,991

Good Deal
Chilton, WI
48 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
119,478
Stock number:
14801A1
VIN:
1GCPYCEF0MZ378830

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

36,980 miles

$32,979

Fair Deal
Milton, WI
47 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
36,980
Stock number:
1968A
VIN:
1GCRYCEF6LZ361683

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

61,218 miles

$35,209

Fair Deal
West Bend, WI
16 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
61,218
Stock number:
WPU472A
VIN:
1GCPYCEL1NZ125782

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

103,379 miles

$30,995

Fair Deal
Greenfield, WI
38 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
103,379
Stock number:
43P1642
VIN:
1GCPYCELXNZ126039

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Wisconsin
  6. / Iron Ridge

  • Chevrolet Silverado 1500 LT in Iron Ridge WI

  • Chevrolet Silverado 1500 RST in Iron Ridge WI

  • Chevrolet Silverado 1500 LTZ in Iron Ridge WI

  • Chevrolet Silverado 1500 LT Trail Boss in Iron Ridge WI

  • Chevrolet Silverado 1500 LT1 in Iron Ridge WI

  • Chevrolet Silverado 1500 High Country in Iron Ridge WI

  • Chevrolet Silverado 1500 Custom in Iron Ridge WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Iron Ridge WI

  • Chevrolet Silverado 1500 Work Truck in Iron Ridge WI

  • Chevrolet Silverado 1500 in Fond du Lac WI

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Appleton WI

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Green Bay WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Iron Ridge WI

  • Old Chevy Trucks for Sale in Iron Ridge WI

  • Classic Muscle Cars for Sale in Iron Ridge WI

  • Chevrolet Trucks For Sale in Iron Ridge WI

  • Cheap Muscle Cars for Sale in Iron Ridge WI

  • Work Trucks for Sale in Iron Ridge WI

  • Reliable Cars For Sale in Iron Ridge WI

  • American Made Trucks For Sale in Iron Ridge WI

  • Best Pickup Trucks For Sale in Iron Ridge WI

  • Best Cars Under $5,000 For Sale in Iron Ridge WI

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Iron Ridge WI

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Kunes Hope Chevrolet

  • Lake Chevrolet

  • Sheboygan Chevrolet GMC

  • Boucher Volkswagen Marketplace

  • Eric von Schledorn Saukville

  • Vande Hey Brantmeier Chevrolet

  • Heiser Chevrolet of West Bend

  • Lynch Chevrolet Mukwonago

  • Newman Chevrolet of Cedarburg

  • Homan Chevrolet GMC of Ripon

  • Napleton Chevrolet Columbus

  • Homan Chevrolet Buick

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.