Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearMadison, WI
195 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2024
- 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:
- 23,806
- Stock #:
- 50243A
- VIN:
- 3GCUDCED6RG122065
Price drop
-$1,000
Sponsored by Ray Chevrolet
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,806 mi
Fox Lake, IL
77 mi away
Great Deal
$38,367
$37,367
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 151,435
- Stock #:
- W15241A
- VIN:
- 3GCPYCEFXLG182604
Price drop
-$1,097
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
151,435 mi
West Bend, WI
64 mi away
Good Deal
$21,993
$20,896
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 43,467
- Stock #:
- Q52516A
- VIN:
- 1GCPYCEF8KZ401946
New arrival
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,467 mi
Dubuque, IA
77 mi away
Fair Deal
$33,138
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Summit White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 59,654
- Stock #:
- 56P106
- VIN:
- 3GCUDCE87PG294329
Price drop
-$711
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,654 mi
Lake Mills, WI
25 mi away
Great Deal
$34,913
$34,202
- Year:
- 2019
- 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:
- Shadow Gray Metallic (gji)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black (h1t)
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 96,517
- Stock #:
- 60391A
- VIN:
- 1GCPYCEH9KZ263965
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
96,517 mi
Mount Horeb, WI
16 mi away
Good Deal
$23,974
- Year:
- 2024
- 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:
- 23,806
- Stock #:
- 50243A
- VIN:
- 3GCUDCED6RG122065
Price drop
-$1,000
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,806 mi
Fox Lake, IL
77 mi away
Great Deal
$38,367
$37,367
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 151,435
- Stock #:
- W15241A
- VIN:
- 3GCPYCEFXLG182604
Price drop
-$1,097
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
151,435 mi
West Bend, WI
64 mi away
Good Deal
$21,993
$20,896
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 123,060
- Stock #:
- P7863B
- VIN:
- 1GCPYCEH3MZ445535
Price drop
-$500
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
123,060 mi
Schaumburg, IL
99 mi away
Good Deal
$22,901
$22,401
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 21,894
- Stock #:
- 1339A
- VIN:
- 3GCUDCED7RG308097
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
21,894 mi
Dubuque, IA
78 mi away
Good Deal
$40,012
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 4,595
- Stock #:
- 24963U
- VIN:
- 3GCUKCED9TG391562
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
4,595 mi
Saukville, WI
77 mi away
Good Deal
$45,398
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 47,030
- Stock #:
- 21432U
- VIN:
- 1GCPYCEF7MZ232067
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
47,030 mi
Antioch, IL
77 mi away
Fair Deal
$32,855
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,018
- Stock #:
- C15352A
- VIN:
- 3GCUDCED2RG379935
Price drop
-$859
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
24,018 mi
Milwaukee, WI
69 mi away
Great Deal
$39,806
$38,947
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- SUMMIT WHITE
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 26,912
- Stock #:
- 26017A
- VIN:
- 3GCPDCEK1RG195534
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
26,912 mi
Appleton, WI
96 mi away
Good Deal
$37,636
- Year:
- 2023
- 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:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 88,539
- Stock #:
- M260624A
- VIN:
- 3GCUDCED4PG163310
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
88,539 mi
Mukwonago, WI
57 mi away
Fair Deal
$33,459
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Black
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 104,356
- Stock #:
- MC260806A
- VIN:
- 3GCUDCE83RG213216
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,356 mi
McHenry, IL
77 mi away
Great Deal
$29,012
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 33,231
- Stock #:
- P14697
- VIN:
- 3GCUDCED3RG228151
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,231 mi
Fox Lake, IL
77 mi away
Good Deal
$39,167
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Cherry Red Tintcoat
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 75,340
- Stock #:
- 138221
- VIN:
- 1GCPYCEK5NZ138221
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
75,340 mi
Dyersville, IA
96 mi away
Fair Deal
$29,149
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 150,130
- Stock #:
- S25550A
- VIN:
- 3GCPYCEF3MG345109
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
150,130 mi
St. Charles, IL
98 mi away
Good Deal
$21,208
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 55,859
- Stock #:
- F1344A
- VIN:
- 3GCPYCEL1NG100154
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,859 mi
Barrington, IL
89 mi away
Good Deal
$32,171
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 99,334
- Stock #:
- R4132A
- VIN:
- 3GCPDCEK5NG678485
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
99,334 mi
Arlington Heights, IL
96 mi away
Great Deal
$24,395
- Year:
- 2019
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 157,898
- VIN:
- 1GCRYCEF4KZ345075
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
157,898 mi
Portage, WI
33 mi away
Fair Deal
$18,264
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 45,829
- Stock #:
- 06T4550A
- VIN:
- 3GCPDCED1NG581625
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
45,829 mi
Elkhorn, WI
50 mi away
Fair Deal
$37,009
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 43,467
- Stock #:
- Q52516A
- VIN:
- 1GCPYCEF8KZ401946
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,467 mi
Dubuque, IA
77 mi away
Fair Deal
$33,138
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 45,829
- Stock #:
- 06T4550A
- VIN:
- 3GCPDCED1NG581625
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
45,829 mi
Elkhorn, WI
50 mi away
Fair Deal
$37,009
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Madison, WI?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $25,697.77. The average price has decreased by -5.5% since last year. The 167 for sale near Madison, WI on CarGurus, range from $18,264 to $55,745 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Madison, WI have no reported accidents or damage?
140 out of 167 for sale near Madison, WI have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG/MPGe.
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
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