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

197 results
Ridgeway, VA
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Jerry Hunt Supercenter of Salisbury

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,435 miles

$37,059

Good Deal
Salisbury, NC
74 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:
39,435
Stock number:
S7869A
VIN:
3GCPDCED1NG662849

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,111 miles

$38,993

Great Deal
Garner, NC
96 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:
Red Hot
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
17,111
Stock number:
GAC12099
VIN:
3GCPDCEK2RG344159

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,489 miles

$43,401

Good Deal
Sanford, NC
89 mi away
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:
Black
Transmission:
Automatic
Mileage:
11,489
Stock number:
T6856
VIN:
3GCUDCED2RG448042

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,270 miles

$44,697

Good Deal
Mount Airy, NC
43 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:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
7,270
Stock number:
C4063B
VIN:
3GCUKCED6SG199871

Preparing for a close up...

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2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,637 miles

$46,300

Good Deal
Kernersville, NC
35 mi away
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:
1,637
Stock number:
259284A
VIN:
3GCUKCED1TG114503

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,778 miles

$38,695

Fair Deal
Siler City, NC
64 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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
32,778
Stock number:
U0170A
VIN:
3GCPDCEK1RG250693

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,217 miles

$39,988

Good Deal
Huntersville, NC
99 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:
Slate Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
31,217
Stock number:
GM18467A
VIN:
3GCPKCEK4SG145187

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,435 miles

$37,059

Good Deal
Salisbury, NC
74 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:
39,435
Stock number:
S7869A
VIN:
3GCPDCED1NG662849

Preparing for a close up...

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,469 miles

$37,200

Fair Deal
Raleigh, NC
78 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
39,469
Stock number:
34199XQ
VIN:
1GCPYCEF9MZ439446

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,504 miles

$39,897

Great Deal
Mount Airy, NC
43 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:
3,504
Stock number:
C3891A
VIN:
3GCPDCEK5RG264449

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,768 miles

$29,989

Fair Deal
Raleigh, NC
87 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:
White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
92,768
Stock number:
MG289402
VIN:
3GCPYCEF5MG289402

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,624 miles

$41,735

Fair Deal
Kernersville, NC
36 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

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,857 miles

$32,991

Fair Deal
Certified Pre-Owned
Greensboro, NC
37 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:
75,857
Stock number:
K23681
VIN:
1GCPYCEF8MZ174177

Preparing for a close up...

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,111 miles

$38,993

Great Deal
Garner, NC
96 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:
Red Hot
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
17,111
Stock number:
GAC12099
VIN:
3GCPDCEK2RG344159

Preparing for a close up...

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,480 miles

$25,998

Good Deal
Pittsboro, NC
71 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
100,480
Stock number:
11519
VIN:
1GCPYCEFXKZ249992

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,869 miles

$42,851

Good Deal
Certified Pre-Owned
Apex, NC
81 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:
Automatic
Mileage:
8,869
Stock number:
T580293A
VIN:
3GCPKCEKXSG328237

Sponsored

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