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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Wasilla, AK

1,900 results

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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
34,291
Stock #:
C392803A
VIN:
3GCPDCEK5PG121904
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Key Chevrolet

Sponsored by Key Chevrolet

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,291 mi

Middletown, CT
3,340 mi away
Fair Deal

$40,989

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:
Glacier Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
71,151
Stock #:
MS55302A
VIN:
3GCPDCED3NG549145
Glacier Blue Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,151 mi

Hampton, VA
3,465 mi away
Good Deal

$36,993

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
Transmission:
Automatic
Mileage:
12,772
Stock #:
28104NF
VIN:
3GCUKCED6SG211971
Slate Gray Metallic 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

12,772 mi

Northfield, OH
3,064 mi away
Good Deal

$44,869

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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
25,885
Stock #:
2501384
VIN:
3GCPDCEK5PG278039
Summit White 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,885 mi

Youngstown, OH
3,109 mi away
Great Deal

$37,098

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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black Cloth Seat Trim
Transmission:
6-Speed Automatic
Mileage:
51,333
Stock #:
5624A
VIN:
1GCPYCEF5KZ384734
Summit White 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,333 mi

Abbeville, AL
3,485 mi away
Good Deal

$32,686

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:
Jet Black
Transmission:
Automatic
Mileage:
26,918
Stock #:
250335A
VIN:
3GCUDCED2RG157945

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,918 mi

Gladstone, MO
2,751 mi away
Good Deal

$41,879

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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
34,711
Stock #:
R4251
VIN:
3GCUDCED0PG335445
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,770

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,711 mi

Lexington, KY
3,144 mi away
Good Deal

$41,528

$39,758

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:
89,509
Stock #:
T27255B
VIN:
1GCPYCEL5NZ149969
Black 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,000

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,509 mi

Cary, NC
3,459 mi away
Good Deal

$32,797

$31,797

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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
65,543
Stock #:
45200109
VIN:
1GCPYCEF5KZ229827
Red Hot 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,543 mi

Bedford, PA
3,231 mi away
Great Deal

$28,995

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:
Red Hot
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
13,489
Stock #:
219972
VIN:
3GCUKCED4SG219972
Red Hot 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,489 mi

Charleston, AR
2,986 mi away
Great Deal
Manufacturer certified

$41,900

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:
23,407
Stock #:
3076E
VIN:
3GCPDCEK7RG229878
Summit White 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$1,075

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,407 mi

Las Vegas, NV
2,299 mi away
Great Deal

$40,453

$39,378

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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
59,563
Stock #:
264346A
VIN:
1GCPYCEF9MZ220244
Shadow Gray Metallic 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,563 mi

Houston, TX
3,255 mi away
Fair Deal

$35,418

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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
59,133
Stock #:
A385276
VIN:
3GCPYCEL5MG385276
White 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,133 mi

Humboldt, IA
2,572 mi away
Fair Deal

$34,800

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:
26,426
Stock #:
RG228408P
VIN:
3GCPDCEK9RG228408
Slate Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,426 mi

Gilroy, CA
2,079 mi away
Good Deal

$39,838

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Red Hot
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
58,290
Stock #:
P1836
VIN:
3GCPYCEK8NG208262
Red Hot 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$1,350

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,290 mi

Schaumburg, IL
2,811 mi away
Good Deal

$34,163

$32,813

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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
84,839
Stock #:
MX4469
VIN:
1GCPYCEF2LZ149662
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 mi

Louisville, TN
3,284 mi away
Good Deal

$29,476

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:
Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
55,339
Stock #:
MX4446
VIN:
1GCPYCEL1MZ352307
Gray 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,339 mi

Louisville, TN
3,284 mi away
Good Deal

$34,476

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:
Jet Black
Transmission:
Automatic
Mileage:
48,095
Stock #:
3081E
VIN:
3GCUDCED7PG294036
Summit White 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,045

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,095 mi

Las Vegas, NV
2,299 mi away
Great Deal

$38,683

$37,638

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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Transmission:
Automatic
Mileage:
79,727
Stock #:
N355141
VIN:
1GCRYCEH4LZ355141
Gray 2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

79,727 mi

Barre, VT
3,204 mi away
Good Deal

$26,294

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:
Glacier Blue Metallic
Fuel type:
Gasoline
Mileage:
33,628
Stock #:
V5273A
VIN:
3GCPDCEK5PG353547
Glacier Blue Metallic 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,628 mi

Columbia, SC
3,485 mi away
Good Deal

$39,759

Year:
2026
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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
3,998
Stock #:
CW60894A
VIN:
3GCPKCEK1TG172381
Sterling Gray Metallic 2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,998 mi

Warwick, RI
3,368 mi away
Good Deal

$46,377

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:
Cypress
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,860
Stock #:
50003A
VIN:
3GCPKCEK1SG296827
Cypress 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,860 mi

Fox Lake, IL
2,788 mi away
Good Deal
Manufacturer certified

$42,110

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