Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWinston, MO
134 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 25,471
- Stock #:
- A10119
- VIN:
- 3GCUKCED0SG277254
Price drop
-$1,756
Sponsored by Heartland Chevrolet
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,471 mi
Liberty, MO
46 mi away
Fair Deal
$46,492
$44,736
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,221
- Stock #:
- 23847
- VIN:
- 1GCPYCEL6NZ159782
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,221 mi
Blue Springs, MO
58 mi away
Good Deal
$36,604
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 28,600
- Stock #:
- 24424
- VIN:
- 3GCPDCEKXNG583906
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,600 mi
Auburn, NE
96 mi away
Fair Deal
$37,995
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,065
- Stock #:
- 22696A
- VIN:
- 3GCPDCEK3PG106074
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,065 mi
Home delivery from Tampa, FL
Price includes $1,108 shipping
Great Deal
$34,597
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,221
- Stock #:
- 23847
- VIN:
- 1GCPYCEL6NZ159782
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,221 mi
Blue Springs, MO
58 mi away
Good Deal
$36,604
- 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:
- 70,422
- Stock #:
- H3735
- VIN:
- 1GCPYCEK4NZ134466
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,422 mi
ODESSA, MO
60 mi away
Good Deal
$31,470
- 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:
- 122,864
- Stock #:
- 175496
- VIN:
- 3GCPYCEF9LG175496
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
122,864 mi
Home delivery from Dawsonville, GA
Price includes $832 shipping
Fair Deal
$26,676
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 71,130
- Stock #:
- 260940BB
- VIN:
- 1GCPYCEF8LZ353107
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
71,130 mi
Home delivery from East Liverpool, OH
Price includes $2,148 shipping
Fair Deal
$32,046
- 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 $637 shipping
Fair Deal
$32,242
- 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 $584 shipping
Great Deal
$29,584
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- White
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 55,891
- Stock #:
- 28383303
- VIN:
- 3GCPYCEK2NG201923
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,891 mi
Store transfer to Independence, MO
Price includes $1,299 shipping
Good Deal
$34,297
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5,703
- Stock #:
- 9217
- VIN:
- 3GCPKCEK9SG334188
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
5,703 mi
Excelsior Springs, MO
37 mi away
Fair Deal
$44,014
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 25,471
- Stock #:
- A10119
- VIN:
- 3GCUKCED0SG277254
Price drop
-$1,756
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,471 mi
Liberty, MO
46 mi away
Fair Deal
$46,492
$44,736
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 28,600
- Stock #:
- 24424
- VIN:
- 3GCPDCEKXNG583906
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,600 mi
Auburn, NE
96 mi away
Fair Deal
$37,995
- 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:
- 83,704
- Stock #:
- 153965B
- VIN:
- 1GCPYCEF5MZ153965
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,704 mi
Home delivery from Dallas, TX
Price includes $512 shipping
Good Deal
$31,237
- 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:
- Sterling Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 31,660
- Stock #:
- 26EQ0622A
- VIN:
- 3GCPDCEK9RG188203
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
31,660 mi
Home delivery from Lewisville, TX
Price includes $750 shipping
Good Deal
$39,492
- 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:
- 75,367
- Stock #:
- 24242
- VIN:
- 1GCPYCEF3MZ198984
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
75,367 mi
Blue Springs, MO
58 mi away
Fair Deal
$33,631
- 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:
- 84,098
- Stock #:
- 20A4806
- VIN:
- 3GCPYCEF1LG436104
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,098 mi
Chillicothe, MO
32 mi away
Good Deal
$30,605
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 1,750
- Stock #:
- DTB3865A
- VIN:
- 3GCUKCED2TG207546
Price drop
-$2,109
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,750 mi
Merriam, KS
66 mi away
Great Deal
$49,374
$47,265
- 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:
- 58,187
- Stock #:
- 105228
- VIN:
- 1GCPYCEL2MZ436815
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,187 mi
Home delivery from Knoxville, TN
Price includes $1,228 shipping
Fair Deal
$38,116
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 70,388
- Stock #:
- 313046
- VIN:
- 3GCUDCED8PG313046
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,388 mi
Home delivery from Euless, TX
Price includes $925 shipping
Good Deal
$36,597
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 105,993
- Stock #:
- 178359
- VIN:
- 1GCPYCEF3LZ178359
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
105,993 mi
Home delivery from Mesa, AZ
Price includes $2,126 shipping
Fair Deal
$28,716
- 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:
- White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 60,897
- Stock #:
- 102757
- VIN:
- 3GCUDCED0PG323361
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,897 mi
Home delivery from Albuquerque, NM
Price includes $1,508 shipping
Fair Deal
$39,256
- 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:
- Cypress Gray
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 11,732
- Stock #:
- 79123A
- VIN:
- 3GCUKCED1SG286058
New arrival
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,732 mi
Lawrence, KS
88 mi away
Good Deal
$45,999
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Winston, MO?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,956.69. The average price has decreased by -0.6% since last year. The 115 for sale near Winston, MO on CarGurus, range from $22,034 to $64,106 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Winston, MO have no reported accidents or damage?
97 out of 115 for sale near Winston, 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 (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
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