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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Wisconsin

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117 vehicles found

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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
79,370
Stock #:
04P2228
VIN:
3GCPDCEK2RG225897
Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic
Kunes Ford of Antioch

Sponsored by Kunes Ford of Antioch

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,370 mi

Antioch, IL
40 mi away
Fair Deal
Third-party certified

$35,313

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:
63,642
Stock #:
G2658A
VIN:
3GCPDCED4NG663283
Dark Ash Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,642 mi

Grayslake, IL
49 mi away
Great Deal

$34,143

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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
68,263
Stock #:
GQ32316
VIN:
3GCPYCEF2MG146410
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,263 mi

Gurnee, IL
45 mi away
Fair Deal
Third-party certified

$33,076

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:
48,383
Stock #:
GP1062
VIN:
1GCPYCEF9LZ210831
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,383 mi

Grayslake, IL
49 mi away
Good Deal

$33,633

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:
63,642
Stock #:
G2658A
VIN:
3GCPDCED4NG663283
Dark Ash Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,642 mi

Grayslake, IL
49 mi away
Great Deal

$34,143

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:
Mosaic Black Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
54,771
Stock #:
5048
VIN:
1GCPYCEL5NZ100710
Mosaic Black Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,771 mi

Home delivery from Seffner, FL
Price includes $1,139 shipping
Great Deal

$33,133

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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
53,768
Stock #:
PM174391
VIN:
1GCPYCEL0NZ174391
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,768 mi

Home delivery from Pleasantville, NJ
Price includes $1,342 shipping
Good Deal

$36,332

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:
Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
26,322
Stock #:
48208
VIN:
3GCUDCED4PG360459
Gray 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,322 mi

Home delivery from Arlington, TX
Price includes $1,308 shipping
Great Deal

$38,528

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:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,775
Stock #:
5019
VIN:
1GCPYCEF0LZ168095
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,775 mi

Home delivery from Burton, MI
Price includes $215 shipping
Great Deal

$29,615

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
Transmission:
6-Speed Automatic Overdrive
Mileage:
33,262
Stock #:
MX4598
VIN:
1GCPYCEF4MZ232253
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,262 mi

Home delivery from Michigan Center, MI
Price includes $344 shipping
Fair Deal

$36,977

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
49,669
Stock #:
28739643
VIN:
1GCPYCEK8NZ237762
Black 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,669 mi

Store transfer to Milwaukee, WI
Price includes $1,599 shipping
Fair Deal

$36,597

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:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
46,774
Stock #:
S19825A
VIN:
3GCUDCED7RG267941
Slate Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,774 mi

Home delivery from Newton, NC
Price includes $934 shipping
Fair Deal

$41,934

Year:
2026
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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
3,560
Stock #:
P25761
VIN:
3GCPKCEK0TG160125
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$1,000

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,560 mi

Home delivery from Scottsdale, AZ
Price includes $1,816 shipping
Good Deal

$46,415

$45,415

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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
79,370
Stock #:
04P2228
VIN:
3GCPDCEK2RG225897
Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,370 mi

Antioch, IL
40 mi away
Fair Deal
Third-party certified

$35,313

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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
68,263
Stock #:
GQ32316
VIN:
3GCPYCEF2MG146410
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,263 mi

Gurnee, IL
45 mi away
Fair Deal
Third-party certified

$33,076

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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
74,770
Stock #:
PT0150
VIN:
1GCRYCEF5KZ198247
Red 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

74,770 mi

Home delivery from Wausau, WI
Price includes $158 shipping
Good Deal

$27,307

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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,122
Stock #:
406-B598
VIN:
1GCPYCEF5KZ375743
Gray 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,122 mi

Home delivery from Huntington, IN
Price includes $582 shipping
Fair Deal

$31,827

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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
115,359
Stock #:
26T378C
VIN:
1GCRYCEH2KZ203485
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

115,359 mi

Home delivery from Sparta, MI
Price includes $224 shipping
Fair Deal

$22,999

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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
85,842
Stock #:
28610308
VIN:
1GCPYCEF2KZ375540
Gray 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

85,842 mi

Store transfer to Milwaukee, WI
Price includes $749 shipping
Fair Deal

$30,747

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:
Dark Ash Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
70,388
Stock #:
313046
VIN:
3GCUDCED8PG313046
Dark Ash Metallic 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,388 mi

Home delivery from Euless, TX
Price includes $1,555 shipping
Fair Deal

$37,227

Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Black Gba
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black H0u
Transmission:
Automatic
Mileage:
14,857
Stock #:
GMT281B1
VIN:
3GCPKCEK7SG176837
Black Gba 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,857 mi

Home delivery from Nitro, WV
Price includes $1,000 shipping
Fair Deal

$45,317

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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
122,864
Stock #:
175496
VIN:
3GCPYCEF9LG175496
Shadow Gray Metallic 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

122,864 mi

Home delivery from Dawsonville, GA
Price includes $785 shipping
Fair Deal

$26,658

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:
35,625
Stock #:
192241I
VIN:
3GCUDCED9RG192241
Black 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,625 mi

Home delivery from Ionia, MI
Price includes $223 shipping
Good Deal

$41,812

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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
185,813
Stock #:
50144A
VIN:
1GCPYCEH8KZ398032
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

Sponsored Listing

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

185,813 mi

Fox Lake, IL
46 mi away
Good Deal

$18,296

FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Wisconsin?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,195.57. The average price has decreased by -1.4% since last year. The 117 for sale near Wisconsin on CarGurus, range from $18,296 to $59,608 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Wisconsin have no reported accidents or damage?
113 out of 117 for sale near Wisconsin 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 (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.

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