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

160 results
Timberville, VA
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Buchanan Auto Park

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,679 miles

$30,844

Fair Deal
Waynesboro, PA
99 mi away
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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,679
Stock number:
B34452
VIN:
1GCPYCEK9NZ119607

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,807 miles

$34,179

Fair Deal
Certified Pre-Owned
Front Royal, VA
35 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,807
Stock number:
R26053A
VIN:
1GCPYCEF2MZ220067

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,493 miles

$35,000

Fair Deal
Manassas, VA
70 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:
Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
49,493
Stock number:
S586862
VIN:
3GCPDCED7NG586862

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,032 miles

$31,990

Good Deal
Fredericksburg, VA
74 mi away
Year:
2020
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
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
40,032
Stock number:
86313H
VIN:
1GCPYCEHXLZ273566

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,863 miles

$32,495

Good Deal
Alexandria, VA
93 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:
Gray
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
72,863
Stock number:
0N16018A
VIN:
3GCPDCEK4PG189224

Preparing for a close up...

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,664 miles

$39,995

Good Deal
Gaithersburg, MD
89 mi away
Year:
2023
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:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
42,664
Stock number:
260075A
VIN:
3GCUDCE84PG293087

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,162 miles

$37,499

Fair Deal
Warrenton, VA
52 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
42,162
Stock number:
P9415
VIN:
1GCPYCELXMZ448890

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,679 miles

$30,844

Fair Deal
Waynesboro, PA
99 mi away
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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,679
Stock number:
B34452
VIN:
1GCPYCEK9NZ119607

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

124,100 miles

$23,999

Great Deal
Forest, VA
95 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:
Gray
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
124,100
Stock number:
4496
VIN:
1GCPYCEF5MZ187565

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Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,807 miles

$34,179

Fair Deal
Certified Pre-Owned
Front Royal, VA
35 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,807
Stock number:
R26053A
VIN:
1GCPYCEF2MZ220067

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,170 miles

$32,250

Fair Deal
Mc Connellsburg, PA
97 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:
Silver Ice Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
66,170
Stock number:
UQ323380
VIN:
1GCPYCEF8LZ323380

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,610 miles

$29,500

Good Deal
Bridgeport, WV
92 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:
66,610
Stock number:
M163392B
VIN:
3GCPYCEF4KG158622

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

115,080 miles

$26,991

Fair Deal
Bedford, PA
96 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:
Havana Brown Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
115,080
Stock number:
UZ201306
VIN:
1GCPYCEF0LZ201306

Sponsored

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