Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWinfield, MO
164 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
47 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black Cloth
- Transmission:
- Automatic
- Mileage:
- 91,713
- Stock #:
- E1003
- VIN:
- 1GCPYCEF3KZ250322
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,713 mi
Hazelwood, MO
27 mi away
Fair Deal
$29,114
- 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 Gba
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 54,776
- Stock #:
- 7751A
- VIN:
- 3GCPDCED0NG679819
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,776 mi
Warrenton, MO
22 mi away
Good Deal
$34,990
- 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 Gba
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 54,776
- Stock #:
- 7751A
- VIN:
- 3GCPDCED0NG679819
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,776 mi
Warrenton, MO
22 mi away
Good Deal
$34,990
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,503
- Stock #:
- T21455B
- VIN:
- 3GCPKCEK3SG339841
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,503 mi
Creve Coeur, MO
29 mi away
Great Deal
$38,818
- 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 $1,184 shipping
Fair Deal
$35,379
- 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:
- Cypress Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 14,487
- Stock #:
- K26347A
- VIN:
- 3GCUKCED0TG122883
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
14,487 mi
Saint Louis, MO
34 mi away
Fair Deal
$47,652
- 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 Cloth
- Transmission:
- Automatic
- Mileage:
- 91,713
- Stock #:
- E1003
- VIN:
- 1GCPYCEF3KZ250322
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,713 mi
Hazelwood, MO
27 mi away
Fair Deal
$29,114
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 158,831
- Stock #:
- C17739A
- VIN:
- 3GCPYCEFXKG173285
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
158,831 mi
Saint Peters, MO
17 mi away
Good Deal
$19,614
- 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 $627 shipping
Fair Deal
$31,422
- 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:
- 62,775
- Stock #:
- 5019
- VIN:
- 1GCPYCEF0LZ168095
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $461 shipping
Great Deal
$29,361
- 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 $454 shipping
Good Deal
$34,744
$30,844
- 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
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $3,206 shipping
Fair Deal
$33,169
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Summit White
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black Cloth
- Transmission:
- Automatic
- Mileage:
- 25,258
- Stock #:
- F261899A
- VIN:
- 3GCUKCE87SG144512
Price drop
-$1,497
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,258 mi
O Fallon, MO
20 mi away
Good Deal
$43,894
$42,397
- 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
Home delivery from Avon, IN
Price includes $358 shipping
Fair Deal
$38,964
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 55,789
- Stock #:
- 105367
- VIN:
- 1GCRYCEF7KZ249845
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
55,789 mi
Home delivery from Knoxville, TN
Price includes $639 shipping
Fair Deal
$30,936
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 93,619
- Stock #:
- KZ188219
- VIN:
- 1GCRYCEF5KZ188219
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
93,619 mi
Home delivery from Tacoma, WA
Price includes $1,683 shipping
Fair Deal
$26,821
- 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
- Mileage:
- 85,722
- Stock #:
- F262012A
- VIN:
- 3GCPYCEK4NG184901
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
85,722 mi
O Fallon, MO
20 mi away
Fair Deal
$30,828
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 46,820
- Stock #:
- 16017
- VIN:
- 3GCPKCEKXSG328917
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,820 mi
Home delivery from Smithfield, NC
Price includes $1,450 shipping
Fair Deal
$39,549
- 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:
- 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 $1,296 shipping
Fair Deal
$30,675
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 57,809
- Stock #:
- MX5448
- VIN:
- 1GCPYCEF7MZ420099
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,809 mi
Home delivery from Michigan Center, MI
Price includes $729 shipping
Good Deal
$32,752
- 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:
- 46,960
- Stock #:
- D9193
- VIN:
- 3GCUDCED0PG363116
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,960 mi
Home delivery from Waukee, IA
Price includes $363 shipping
Good Deal
$38,624
- 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 $370 shipping
Good Deal
$29,148
- 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:
- Red Hot
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Mileage:
- 75,125
- Stock #:
- 13022XA
- VIN:
- 3GCUDCED4PG232061
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
75,125 mi
Florissant, MO
30 mi away
Fair Deal
$38,094
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Winfield, MO?
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 164 for sale near Winfield, MO on CarGurus, range from $19,614 to $64,273 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Winfield, MO have no reported accidents or damage?
156 out of 164 for sale near Winfield, MO 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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