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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Check, VA

158 results
Copper Hill, VA
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Kernersville Chrysler Dodge

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,624 miles

$40,435

Good Deal
Kernersville, NC
65 mi away
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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,624
Stock number:
Y0342
VIN:
3GCUDCED7PG307660

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,000 miles

$46,991

Fair Deal
Martinsville, VA
31 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Summit White
Fuel type:
Diesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
21,000
Stock number:
H7616A
VIN:
3GCUKCE8XSG249254

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,834 miles

$38,885

Good Deal
Staunton, VA
95 mi away
Year:
2023
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:
Black
Transmission:
8-Speed Automatic
Mileage:
11,834
Stock number:
N07240A
VIN:
3GCPDCEKXPG281941

Sponsored

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,417 miles

$32,497

Great Deal
Store transfer to Roanoke, VA
256 mi away • Price includes $499 shipping Price includes $499 shipping
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:
50,417
Stock number:
27851520
VIN:
3GCPYCEK9NG185283

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,533 miles

$35,596

Good Deal
Summersville, WV
94 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Silver Ice Metallic
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,533
Stock number:
800151A
VIN:
1GCPYCEK5NZ230719

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,651 miles

$28,988

Fair Deal
Lexington, NC
84 mi away
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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
80,651
Stock number:
25997A
VIN:
3GCPYCEF6KG268247

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,038 miles

$46,449

Good Deal
Covington, VA
51 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Cypress Gray
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
4,038
Stock number:
P12572-3
VIN:
3GCUKCEDXSG343437

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,593 miles

$38,068

Good Deal
Mount Hope, WV
79 mi away
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
33,593
Stock number:
RG231181
VIN:
3GCPDCEK0RG231181

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,896 miles

$45,348

Good Deal
Salisbury, NC
98 mi away
Year:
2025
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:
Automatic
Mileage:
17,896
Stock number:
S8409
VIN:
3GCUKCED2SG294802

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,403 miles

$40,134

Good Deal
High Point, NC
77 mi away
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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
29,403
Stock number:
173589A
VIN:
3GCPKCEKXSG173589

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,899 miles

$42,447

Good Deal
Store transfer to Roanoke, VA
471 mi away • Price includes $449 shipping Price includes $449 shipping
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:
White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
5,899
Stock number:
28455695
VIN:
3GCPKCEK0SG323144

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,834 miles

$38,885

Good Deal
Staunton, VA
95 mi away
Year:
2023
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:
Black
Transmission:
8-Speed Automatic
Mileage:
11,834
Stock number:
N07240A
VIN:
3GCPDCEKXPG281941

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,445 miles

$27,885

Fair Deal
Graham, NC
81 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:
Shadow Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
101,445
Stock number:
13765
VIN:
3GCPYCEF4LG178774

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,896 miles

$45,348

Good Deal
Salisbury, NC
98 mi away
Year:
2025
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:
Automatic
Mileage:
17,896
Stock number:
S8409
VIN:
3GCUKCED2SG294802

Sponsored

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