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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Castle Rock, CO

92 results
Castle Rock, CO
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Foundation Chevrolet

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,212 miles

$44,299

Fair Deal
Certified Pre-Owned
Wheat Ridge, CO
31 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:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,212
Stock number:
RG376454T
VIN:
3GCUDCED4RG376454

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

103,752 miles

$27,958

Fair Deal
Colorado Springs, CO
33 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:
Gray
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
103,752
Stock number:
24716
VIN:
1GCPYCEFXLZ101097

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,217 miles

$32,899

Fair Deal
Certified Pre-Owned
Denver, CO
21 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
73,217
Stock number:
DP13281A
VIN:
1GCPYCEF9MZ288592

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,297 miles

$32,062

Good Deal
Certified Pre-Owned
Brighton, CO
40 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Shadow Gray Metallic
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
59,297
Stock number:
15898A
VIN:
1GCPYCEK5NZ196703

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,463 miles

$34,000

Fair Deal
Littleton, CO
18 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:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
54,463
Stock number:
LG403899
VIN:
3GCPYCEF0LG403899

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

112,198 miles

$22,998

Great Deal
Colorado Springs, CO
37 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:
White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
112,198
Stock number:
P9929
VIN:
1GCRYCEF8LZ223496

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,217 miles

$32,899

Fair Deal
Certified Pre-Owned
Denver, CO
21 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
73,217
Stock number:
DP13281A
VIN:
1GCPYCEF9MZ288592

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,107 miles

$37,010

Good Deal
Colorado Springs, CO
38 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:
Northsky Blue Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
25,107
Stock number:
AMZ172947
VIN:
1GCPYCEFXMZ172947

Preparing for a close up...

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,223 miles

$38,797

Fair Deal
Store transfer to Parker, CO
767 mi away • Price includes $799 shipping Price includes $799 shipping
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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
29,223
Stock number:
27645856
VIN:
3GCPDCED6NG585654

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,843 miles

$37,998

Good Deal
Colorado Springs, CO
37 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:
White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
25,843
Stock number:
Z6590
VIN:
3GCPDCEK8PG106197

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,212 miles

$44,299

Fair Deal
Certified Pre-Owned
Wheat Ridge, CO
31 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:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,212
Stock number:
RG376454T
VIN:
3GCUDCED4RG376454

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,076 miles

$32,999

Fair Deal
Denver, CO
23 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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
72,076
Stock number:
399479
VIN:
1GCPYCEF9MZ399479

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,717 miles

$41,587

Good Deal
Certified Pre-Owned
Colorado Springs, CO
37 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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
15,717
Stock number:
S360535
VIN:
3GCPDCEK7RG360535

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,297 miles

$32,062

Good Deal
Certified Pre-Owned
Brighton, CO
40 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Shadow Gray Metallic
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
59,297
Stock number:
15898A
VIN:
1GCPYCEK5NZ196703

Sponsored

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  4. / Custom Trail Boss
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