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

176 results
Culpeper, VA
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Lindsay Chevrolet of Woodbridge

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,427 miles

$43,900

Good Deal
Woodbridge, VA
41 mi away
Year:
2024
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:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
17,427
Stock number:
HP9460
VIN:
3GCUDCE81RG264438

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

2,924 miles

$43,100

Good Deal
Clarksville, MD
78 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
2,924
Stock number:
C1255
VIN:
3GCUDCEDXRG251863

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
34 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

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
31 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

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,286 miles

$28,997

Great Deal
Certified Pre-Owned
Glen Burnie, MD
90 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:
73,286
Stock number:
C1612N
VIN:
3GCPYCEK7NG117225

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,567 miles

$34,245

Great Deal
Thurmont, MD
87 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:
Sand Dune Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
42,567
Stock number:
Q250648A
VIN:
3GCPDCEK0PG122197

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,963 miles

$33,750

Great Deal
Alexandria, VA
55 mi away
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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
14,963
Stock number:
E23556G
VIN:
1GCPYCEH9MZ189983

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,162 miles

$37,499

Fair Deal
Warrenton, VA
23 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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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,807 miles

$34,179

Fair Deal
Certified Pre-Owned
Front Royal, VA
34 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

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,679 miles

$30,844

Good Deal
Waynesboro, PA
93 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

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,863 miles

$32,995

Good Deal
Alexandria, VA
58 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

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,664 miles

$39,995

Great Deal
Gaithersburg, MD
65 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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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,165 miles

$38,440

Good Deal
Springfield, VA
50 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:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
29,165
Stock number:
GCKE174H
VIN:
3GCPDCEK3RG276938

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

86,399 miles

$25,931

Fair Deal
Glen Burnie, MD
91 mi away
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:
Red
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
86,399
Stock number:
255632A
VIN:
1GCRYCEH8KZ405733

Sponsored

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  5. / Virginia
  6. / Culpeper
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