Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearAnna, IL
181 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black Cloth
- Transmission:
- Automatic
- Mileage:
- 4,177
- Stock #:
- T260856A
- VIN:
- 3GCPKCEK6TG127131
Sponsored by George Weber Chevrolet Columbia
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
4,177 mi
Columbia, IL
91 mi away
Good Deal
$44,377
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 116,663
- Stock #:
- KZ198554
- VIN:
- 1GCPYCEF4KZ198554
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
116,663 mi
Hillsboro, MO
93 mi away
Good Deal
$24,250
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 98,185
- Stock #:
- 267484
- VIN:
- 1GCRYCEF6KZ302129
Price drop
-$1,100
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
98,185 mi
Herculaneum, MO
87 mi away
Fair Deal
$26,535
$25,985
- 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 $379 shipping
Good Deal
$34,669
$30,769
- 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:
- 32,017
- Stock #:
- 8T617F
- VIN:
- 3GCUDCED3RG201855
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,017 mi
Home delivery from Scottsboro, AL
Price includes $393 shipping
Good Deal
$42,853
- 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 Cloth
- Transmission:
- Automatic
- Mileage:
- 119,373
- Stock #:
- 6111001
- VIN:
- 3GCPYCEK8NG184464
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
119,373 mi
Saint Louis, MO
96 mi away
Good Deal
$26,594
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 31,295
- Stock #:
- SG211397
- VIN:
- 3GCUKCED0SG211397
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
31,295 mi
Home delivery from Benton, AR
Price includes $332 shipping
Good Deal
$42,013
- 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 $942 shipping
Fair Deal
$35,137
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 35,087
- Stock #:
- 26GT291A
- VIN:
- 3GCUDCE85PG278582
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,087 mi
Paris, TN
92 mi away
Fair Deal
$42,389
- 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 $582 shipping
Fair Deal
$31,377
- 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
- Transmission:
- Automatic
- Mileage:
- 58,728
- Stock #:
- 4231B
- VIN:
- 1GCPYCEL4MZ341639
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,728 mi
New Athens, IL
71 mi away
Fair Deal
$35,137
- 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:
- Red Hot
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,117
- Stock #:
- 204476P
- VIN:
- 1GCRYCEF6LZ204476
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
63,117 mi
Paducah, KY
38 mi away
Fair Deal
$30,681
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 116,663
- Stock #:
- KZ198554
- VIN:
- 1GCPYCEF4KZ198554
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
116,663 mi
Hillsboro, MO
93 mi away
Good Deal
$24,250
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 71,652
- Stock #:
- A88197
- VIN:
- 1GCPYCEF1MZ270913
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
71,652 mi
Herculaneum, MO
87 mi away
Fair Deal
$33,049
- 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 (Charcoal)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 135,132
- Stock #:
- 250850
- VIN:
- 1GCPYCEF4LZ250850
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
135,132 mi
Home delivery from Salt Lake City, UT
Price includes $1,852 shipping
Fair Deal
$23,752
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,807
- Stock #:
- SG102884T
- VIN:
- 3GCPKCEK9SG102884
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,807 mi
Home delivery from Dallas, TX
Price includes $537 shipping
Fair Deal
$38,758
- 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:
- 22,830
- Stock #:
- SG288217
- VIN:
- 3GCPKCEK0SG288217
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,830 mi
Home delivery from Searcy, AR
Price includes $216 shipping
Good Deal
$40,027
- 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:
- GRY
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 62,918
- Stock #:
- 11258
- VIN:
- 3GCPDCED1NG673222
Price drop
-$1,266
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,918 mi
Home delivery from Blackwood, NJ
Price includes $778 shipping
Good Deal
$36,626
$35,360
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 123,973
- Stock #:
- S0251
- VIN:
- 3GCPDCED2NG505718
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
123,973 mi
Home delivery from Cleveland, TN
Price includes $292 shipping
Fair Deal
$28,586
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 58,210
- Stock #:
- 4797
- VIN:
- 3GCPYCEFXKG146393
Price drop
-$1,600
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,210 mi
Home delivery from Cartersville, GA
Price includes $500 shipping
Good Deal
$32,797
$31,196
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 127,135
- Stock #:
- PN532854A
- VIN:
- 3GCPYCEH0KG135095
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
127,135 mi
Madisonville, KY
93 mi away
Fair Deal
$24,299
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 98,185
- Stock #:
- 267484
- VIN:
- 1GCRYCEF6KZ302129
Price drop
-$1,100
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
98,185 mi
Herculaneum, MO
87 mi away
Fair Deal
$26,535
$25,985
- 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:
- 75,533
- Stock #:
- MG458150
- VIN:
- 3GCPYCEL9MG458150
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
75,533 mi
Home delivery from Benton, AR
Price includes $332 shipping
Good Deal
$31,379
- 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:
- Red Hot
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,117
- Stock #:
- 204476P
- VIN:
- 1GCRYCEF6LZ204476
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
63,117 mi
Paducah, KY
38 mi away
Fair Deal
$30,681
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Anna, IL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,451.15. The average price has decreased by -2.3% since last year. The 170 for sale near Anna, IL on CarGurus, range from $20,949 to $64,402 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Anna, IL have no reported accidents or damage?
140 out of 170 for sale near Anna, IL 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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