Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWinamac, IN
230 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 106,418
- Stock #:
- SS1632
- VIN:
- 1GCRYCEF4KZ403413
Sponsored by Indy Auto Man
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
106,418 mi
Indianapolis, IN
96 mi away
Fair Deal
$25,841
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 86,469
- Stock #:
- NS1593
- VIN:
- 1GCRYCEH0KZ240602
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
86,469 mi
Westfield, IN
74 mi away
Great Deal
$24,772
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 50,624
- Stock #:
- T26138A
- VIN:
- 1GCPYCEF7MZ248026
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,624 mi
Indianapolis, IN
93 mi away
Fair Deal
$35,048
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 64,213
- Stock #:
- B7006B
- VIN:
- 1GCRYCEF1KZ343008
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
64,213 mi
Bourbonnais, IL
64 mi away
Fair Deal
$29,996
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 93,117
- Stock #:
- AA568A
- VIN:
- 1GCPYCEK1NZ115843
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,117 mi
Fort Wayne, IN
79 mi away
Fair Deal
$28,836
- 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:
- Cherry Red Tintcoat
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 83,964
- Stock #:
- C26460A
- VIN:
- 1GCPYCEF2MZ364900
Price drop
-$972
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,964 mi
Avon, IN
89 mi away
Great Deal
$28,624
$27,914
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 41,895
- Stock #:
- P10762
- VIN:
- 1GCPYCEF5LZ145816
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,895 mi
Naperville, IL
95 mi away
Good Deal
$31,488
- 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
84 mi away
Great Deal
$36,490
- 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 Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 86,984
- Stock #:
- YP716
- VIN:
- 1GCPYCEH4KZ399582
Price drop
-$2,762
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
86,984 mi
Danville, IL
78 mi away
Great Deal
$28,607
$25,845
- 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:
- Blue
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 79,997
- Stock #:
- 256943
- VIN:
- 1GCPYCEF6MZ256943
Price drop
-$3,900
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
79,997 mi
Home delivery from Monroe, LA
Price includes $662 shipping
Good Deal
$34,952
$31,052
- 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 GRAY
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 11,352
- Stock #:
- 277668A
- VIN:
- 3GCPKCEK7SG347277
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,352 mi
Home delivery from Madison, WI
Price includes $195 shipping
Fair Deal
$44,422
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,716
- Stock #:
- CC2036
- VIN:
- 3GCPDCEK8RG179394
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,716 mi
Avon, IN
89 mi away
Fair Deal
$38,606
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 76,524
- Stock #:
- C4914A
- VIN:
- 3GCPYCEF6MG480715
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,524 mi
Morris, IL
94 mi away
Good Deal
$31,376
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 80,389
- Stock #:
- 103642
- VIN:
- 3GCPDCEK6RG103642
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
80,389 mi
Home delivery from Mobile, AL
Price includes $1,446 shipping
Fair Deal
$35,641
- 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:
- 29,882
- Stock #:
- 7-207477A
- VIN:
- 3GCUKCED4SG130287
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,882 mi
Home delivery from Durand, MI
Price includes $558 shipping
Fair Deal
$44,904
- 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:
- 35,093
- Stock #:
- HCVPPG361993
- VIN:
- 3GCUDCED7PG361993
Price drop
-$800
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,093 mi
Noblesville, IN
77 mi away
Great Deal
$39,010
$38,210
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,773
- Stock #:
- 54173
- VIN:
- 3GCPDCEK6NG533147
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,773 mi
Home delivery from Cambridge, OH
Price includes $206 shipping
Good Deal
$28,983
- 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:
- SAND DUNE METALLIC
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $834 shipping
Fair Deal
$31,629
- 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:
- 51,002
- Stock #:
- 26582A
- VIN:
- 1GCPYCEF3MZ403056
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,002 mi
Peotone, IL
63 mi away
Fair Deal
$34,413
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 93,538
- Stock #:
- 261430A
- VIN:
- 1GCPYCEH5LZ331244
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,538 mi
Oak Lawn, IL
74 mi away
Good Deal
$25,711
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 92,923
- Stock #:
- VC26183
- VIN:
- 1GCPYCEFXKZ269806
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,923 mi
Hicksville, OH
99 mi away
Fair Deal
$27,390
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 85,125
- Stock #:
- V8606TA
- VIN:
- 1GCPYCEL2MZ368273
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
85,125 mi
Vicksburg, MI
93 mi away
Good Deal
$30,939
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 116,986
- Stock #:
- A666A
- VIN:
- 1GCPYCEF6LZ373758
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
116,986 mi
Dwight, IL
93 mi away
Fair Deal
$25,356
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 92,923
- Stock #:
- VC26183
- VIN:
- 1GCPYCEFXKZ269806
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,923 mi
Hicksville, OH
99 mi away
Fair Deal
$27,390
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Winamac, IN?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,418.75. The average price has decreased by -2.5% since last year. The 184 for sale near Winamac, IN on CarGurus, range from $21,300 to $64,722 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Winamac, IN have no reported accidents or damage?
176 out of 184 for sale near Winamac, 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.
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