Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearUpland, IN
233 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 19,243
- Stock #:
- C261917A
- VIN:
- 3GCUKCED2SG354738
New arrival
Sponsored by Joseph Chevrolet
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,243 mi
Cincinnati, OH
97 mi away
Good Deal
$42,448
- 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
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,240 mi
Dayton, OH
90 mi away
Good Deal
$34,393
- 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:
- 1,960
- Stock #:
- C39518
- VIN:
- 3GCUKCED3TG336539
New arrival
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,960 mi
Cincinnati, OH
97 mi away
Good Deal
$47,555
- 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:
- 19,054
- Stock #:
- 70253003
- VIN:
- 3GCPDCEKXRG335791
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,054 mi
Store transfer to Indianapolis, IN
Price includes $749 shipping
Good Deal
$37,747
- 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
90 mi away
Good Deal
$34,393
- 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
Price drop
-$2,892
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
$43,671
$40,779
- 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
26 mi away
Great Deal
$35,000
- 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 $1,257 shipping
Good Deal
$33,073
- 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
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,797 mi
Avon, IN
69 mi away
Fair Deal
$29,378
- 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:
- 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 $3,658 shipping
Fair Deal
$33,621
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,142
- Stock #:
- P36571
- VIN:
- 3GCPDCEK4RG151995
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,142 mi
Home delivery from Flint, MI
Price includes $296 shipping
Good Deal
$36,610
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 93,992
- Stock #:
- 144813B
- VIN:
- 1GCPYCEK5NZ144813
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,992 mi
Home delivery from Dallas, TX
Price includes $821 shipping
Fair Deal
$27,546
- 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:
- Automatic
- Mileage:
- 108,735
- Stock #:
- PM31343
- VIN:
- 1GCPYCEF5LZ274946
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
108,735 mi
Kokomo, IN
32 mi away
Fair Deal
$27,528
- 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
96 mi away
Fair Deal
$29,097
- 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:
- 150,607
- Stock #:
- 7191A
- VIN:
- 1GCPYCEF2MZ255191
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
150,607 mi
Home delivery from Hazard, KY
Price includes $750 shipping
Fair Deal
$23,049
- 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
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,964 mi
Avon, IN
66 mi away
Good Deal
$28,427
- 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
86 mi away
Fair Deal
$40,875
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 73,083
- Stock #:
- GO8518
- VIN:
- 1GCRYCEF3KZ336318
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
73,083 mi
Home delivery from Grand Blanc, MI
Price includes $390 shipping
Good Deal
$26,204
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 19,243
- Stock #:
- C261917A
- VIN:
- 3GCUKCED2SG354738
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,243 mi
Cincinnati, OH
97 mi away
Good Deal
$42,448
- 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:
- 109,106
- Stock #:
- 85370A
- VIN:
- 1GCPYCEF9MZ268116
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
109,106 mi
Home delivery from Mentor, OH
Price includes $348 shipping
Fair Deal
$27,291
- 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:
- Red
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2,752
- Stock #:
- 55TG242880P
- VIN:
- 3GCUKCED2TG242880
Price drop
-$1,648
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,752 mi
Springfield, OH
95 mi away
Great Deal
$45,575
$43,927
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 57,550
- Stock #:
- KZ370333T
- VIN:
- 1GCRYCEF4KZ370333
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
57,550 mi
Home delivery from Egg Harbor Township, NJ
Price includes $870 shipping
Good Deal
$29,108
- 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
98 mi away
Good Deal
$43,039
- 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
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,535 mi
Lebanon, OH
98 mi away
Good Deal
$43,039
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Upland, IN?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,077.34. The average price has decreased by -4.6% since last year. The 200 for sale near Upland, IN on CarGurus, range from $19,124 to $62,819 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Upland, IN have no reported accidents or damage?
178 out of 200 for sale near Upland, 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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