Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearPortland, IN
252 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Cypress Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 115
- Stock #:
- G136321
- VIN:
- 3GCPKCEK1TG136321
Sponsored by Exceptional Motor Car
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
115 mi
Defiance, OH
66 mi away
Good Deal
$44,188
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,913
- Stock #:
- 261875A
- VIN:
- 3GCPDCEK0PG271208
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,913 mi
Indianapolis, IN
81 mi away
Fair Deal
$38,999
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,155
- Stock #:
- 57250SA
- VIN:
- 3GCPKCEK2SG154874
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,155 mi
Miamisburg, OH
66 mi away
Fair Deal
$40,375
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 109,649
- Stock #:
- G7777
- VIN:
- 1GCPYCEKXNZ203922
Price drop
-$1,700
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
109,649 mi
Marion, OH
99 mi away
Good Deal
$27,148
$25,448
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Sand Dune Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,240
- Stock #:
- C16139
- VIN:
- 3GCUDCET0NG535858
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,240 mi
Dayton, OH
69 mi away
Good Deal
$33,893
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 35,072
- Stock #:
- HCVPRG216142
- VIN:
- 3GCUDCED8RG216142
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,072 mi
Noblesville, IN
60 mi away
Good Deal
$40,210
- 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:
- 1,535
- Stock #:
- 260136A
- VIN:
- 3GCUDCED4PG334766
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,535 mi
Lebanon, OH
79 mi away
Good Deal
$42,839
- 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
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 84,697
- Stock #:
- FP11476
- VIN:
- 1GCPYCEF4LZ133947
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,697 mi
Fairfield, OH
78 mi away
Great Deal
$26,355
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 83,797
- Stock #:
- CC2056AA
- VIN:
- 3GCPYCEF4LG144026
Price drop
-$1,302
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,797 mi
Avon, IN
89 mi away
Fair Deal
$29,378
$28,336
- 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
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,302
- Stock #:
- 269833
- VIN:
- 3GCPYCEF0LG269833
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,302 mi
West Chester, OH
80 mi away
Fair Deal
$29,097
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,155
- Stock #:
- 57250SA
- VIN:
- 3GCPKCEK2SG154874
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,155 mi
Miamisburg, OH
66 mi away
Fair Deal
$40,375
- 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:
- 39,306
- Stock #:
- AT6263
- VIN:
- 1GCPYCEFXMZ368466
Price drop
-$1,106
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,306 mi
West Chester, OH
83 mi away
Good Deal
$35,392
$34,286
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2,051
- Stock #:
- C39518
- VIN:
- 3GCUKCED3TG336539
Price drop
-$1,369
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,051 mi
Cincinnati, OH
83 mi away
Good Deal
$47,555
$46,186
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Slate Gray Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 52,778
- Stock #:
- B19182A
- VIN:
- 3GCUDCE8XRG358530
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
52,778 mi
Anderson, IN
42 mi away
Great Deal
$35,000
- 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:
- 9,084
- Stock #:
- P6923
- VIN:
- 3GCUDCED2PG295840
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
9,084 mi
Lebanon, OH
79 mi away
Good Deal
$42,039
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 42,114
- Stock #:
- MG311737
- VIN:
- 3GCPYCEF5MG311737
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
42,114 mi
Home delivery from Corsicana, TX
Price includes $1,286 shipping
Good Deal
$32,400
- 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:
- 863
- Stock #:
- M45201
- VIN:
- 3GCUDCED3PG278724
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
863 mi
Fort Wayne, IN
50 mi away
Good Deal
$43,807
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 32,122
- Stock #:
- 34-1577P
- VIN:
- 3GCUKCED0SG119948
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,122 mi
Home delivery from Burns Harbor, IN
Price includes $500 shipping
Good Deal
$39,283
- 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:
- 41,790
- Stock #:
- NG204699
- VIN:
- 3GCPYCEL4NG204699
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,790 mi
Cincinnati, OH
85 mi away
Great Deal
$32,929
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 73,652
- Stock #:
- 28380132
- VIN:
- 3GCPYCEF7LG258294
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
73,652 mi
Store transfer to Fort Wayne, IN
Price includes $199 shipping
Fair Deal
$32,197
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 40,399
- Stock #:
- P8273C
- VIN:
- 3GCUDCED5RG298170
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
40,399 mi
Fort Wayne, IN
50 mi away
Fair Deal
$39,548
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,297
- Stock #:
- 270102
- VIN:
- 1GCPYCEF8MZ270102
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $3,710 shipping
Fair Deal
$33,673
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 60,685
- Stock #:
- MZ321296
- VIN:
- 1GCPYCEF7MZ321296
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,685 mi
Cincinnati, OH
85 mi away
Good Deal
$31,248
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 26,745
- Stock #:
- 63664A
- VIN:
- 3GCUDCED1PG357860
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
26,745 mi
Lafayette, IN
99 mi away
Good Deal
$41,046
- 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:
- Cypress Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 115
- Stock #:
- G136321
- VIN:
- 3GCPKCEK1TG136321
Sponsored by Exceptional Motor Car
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
115 mi
Defiance, OH
66 mi away
Good Deal
$44,188
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,913
- Stock #:
- 261875A
- VIN:
- 3GCPDCEK0PG271208
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,913 mi
Indianapolis, IN
81 mi away
Fair Deal
$38,999
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,155
- Stock #:
- 57250SA
- VIN:
- 3GCPKCEK2SG154874
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,155 mi
Miamisburg, OH
66 mi away
Fair Deal
$40,375
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 109,649
- Stock #:
- G7777
- VIN:
- 1GCPYCEKXNZ203922
Price drop
-$1,700
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
109,649 mi
Marion, OH
99 mi away
Good Deal
$27,148
$25,448
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Sand Dune Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,240
- Stock #:
- C16139
- VIN:
- 3GCUDCET0NG535858
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,240 mi
Dayton, OH
69 mi away
Good Deal
$33,893
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 35,072
- Stock #:
- HCVPRG216142
- VIN:
- 3GCUDCED8RG216142
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,072 mi
Noblesville, IN
60 mi away
Good Deal
$40,210
- 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:
- 1,535
- Stock #:
- 260136A
- VIN:
- 3GCUDCED4PG334766
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,535 mi
Lebanon, OH
79 mi away
Good Deal
$42,839
- 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
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 84,697
- Stock #:
- FP11476
- VIN:
- 1GCPYCEF4LZ133947
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,697 mi
Fairfield, OH
78 mi away
Great Deal
$26,355
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 83,797
- Stock #:
- CC2056AA
- VIN:
- 3GCPYCEF4LG144026
Price drop
-$1,302
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,797 mi
Avon, IN
89 mi away
Fair Deal
$29,378
$28,336
- 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
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,302
- Stock #:
- 269833
- VIN:
- 3GCPYCEF0LG269833
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,302 mi
West Chester, OH
80 mi away
Fair Deal
$29,097
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,155
- Stock #:
- 57250SA
- VIN:
- 3GCPKCEK2SG154874
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,155 mi
Miamisburg, OH
66 mi away
Fair Deal
$40,375
- 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:
- 39,306
- Stock #:
- AT6263
- VIN:
- 1GCPYCEFXMZ368466
Price drop
-$1,106
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,306 mi
West Chester, OH
83 mi away
Good Deal
$35,392
$34,286
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2,051
- Stock #:
- C39518
- VIN:
- 3GCUKCED3TG336539
Price drop
-$1,369
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,051 mi
Cincinnati, OH
83 mi away
Good Deal
$47,555
$46,186
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Slate Gray Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 52,778
- Stock #:
- B19182A
- VIN:
- 3GCUDCE8XRG358530
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
52,778 mi
Anderson, IN
42 mi away
Great Deal
$35,000
- 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:
- 9,084
- Stock #:
- P6923
- VIN:
- 3GCUDCED2PG295840
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
9,084 mi
Lebanon, OH
79 mi away
Good Deal
$42,039
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 42,114
- Stock #:
- MG311737
- VIN:
- 3GCPYCEF5MG311737
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
42,114 mi
Home delivery from Corsicana, TX
Price includes $1,286 shipping
Good Deal
$32,400
- 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:
- 863
- Stock #:
- M45201
- VIN:
- 3GCUDCED3PG278724
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
863 mi
Fort Wayne, IN
50 mi away
Good Deal
$43,807
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 32,122
- Stock #:
- 34-1577P
- VIN:
- 3GCUKCED0SG119948
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,122 mi
Home delivery from Burns Harbor, IN
Price includes $500 shipping
Good Deal
$39,283
- 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:
- 41,790
- Stock #:
- NG204699
- VIN:
- 3GCPYCEL4NG204699
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,790 mi
Cincinnati, OH
85 mi away
Great Deal
$32,929
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 73,652
- Stock #:
- 28380132
- VIN:
- 3GCPYCEF7LG258294
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
73,652 mi
Store transfer to Fort Wayne, IN
Price includes $199 shipping
Fair Deal
$32,197
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 40,399
- Stock #:
- P8273C
- VIN:
- 3GCUDCED5RG298170
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
40,399 mi
Fort Wayne, IN
50 mi away
Fair Deal
$39,548
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,297
- Stock #:
- 270102
- VIN:
- 1GCPYCEF8MZ270102
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $3,710 shipping
Fair Deal
$33,673
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 60,685
- Stock #:
- MZ321296
- VIN:
- 1GCPYCEF7MZ321296
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,685 mi
Cincinnati, OH
85 mi away
Good Deal
$31,248
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 26,745
- Stock #:
- 63664A
- VIN:
- 3GCUDCED1PG357860
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
26,745 mi
Lafayette, IN
99 mi away
Good Deal
$41,046
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Portland, IN?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $25,962.55. The average price has decreased by -5.2% since last year. The 199 for sale near Portland, IN on CarGurus, range from $18,903 to $62,367 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Portland, IN have no reported accidents or damage?
172 out of 199 for sale near Portland, IN have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG/MPGe.
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
Relevant articles
Drew Johnson
The Cheapest New Trucks on Sale in 2026
Is there such a thing as a cheap new truck any more? Absolutely! Here's our expert guide to the top 10 cheapest new trucks on sale.
CarGurus Editorial Team
Best Cars for New Parents
Discover the best family cars for first-time parents in 2025, accounting for door access, car seat compatibility, and other real-world considerations new parents will want to keep in mind.
CarGurus Editorial Team
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Chevrolet Silverado 1500 LT in Portland INChevrolet Silverado 1500 RST in Portland INChevrolet Silverado 1500 LTZ in Portland INChevrolet Silverado 1500 LT Trail Boss in Portland INChevrolet Silverado 1500 LT1 in Portland INChevrolet Silverado 1500 Custom in Portland INChevrolet Silverado 1500 High Country in Portland INChevrolet Silverado 1500 Custom Trail Boss in Portland INChevrolet Silverado 1500 Work Truck in Portland IN
Chevrolet Silverado 1500 in Anderson INChevrolet Silverado 1500 in Fort Wayne INChevrolet Silverado 1500 in Lima OHChevrolet Silverado 1500 in Kokomo INChevrolet Silverado 1500 in Dayton OHChevrolet Silverado 1500 in Indianapolis INChevrolet Silverado 1500 in Cincinnati OHChevrolet Silverado 1500 in Columbus INChevrolet Silverado 1500 in Marion OH
Chevrolet Silverado 1500 in Portland INOld Chevy Trucks for Sale in Portland INClassic Muscle Cars for Sale in Portland INChevrolet Trucks For Sale in Portland INCheap Muscle Cars for Sale in Portland INWork Trucks for Sale in Portland INReliable Cars For Sale in Portland INAmerican Made Trucks For Sale in Portland INBest Pickup Trucks For Sale in Portland INBest Cars Under $5,000 For Sale in Portland IN
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in PortlandUsed SUVs / Crossovers for Sale with Low Mileage in PortlandUsed Hatchbacks for Sale with Low Mileage in PortlandUsed Convertibles for Sale with Low Mileage in PortlandUsed Vans for Sale with Low Mileage in PortlandUsed Minivans for Sale with Low Mileage in PortlandUsed Pickup Trucks for Sale with Low Mileage in PortlandUsed Coupes for Sale with Low Mileage in PortlandUsed Wagons for Sale with Low Mileage in Portland
