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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Jackson, MO

146 results

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:
Red Hot
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black Cloth
Transmission:
Automatic
Mileage:
28,698
Stock #:
19928B
VIN:
3GCPKCEK2SG190869
Red Hot 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
Weber Ford

Sponsored by Weber Ford

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

28,698 mi

Granite City, IL
94 mi away
Good Deal
Third-party certified

$40,789

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:
White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
164,410
Stock #:
KZ250639
VIN:
1GCRYCEF9KZ250639
White 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

Sponsored Listing

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

164,410 mi

Hillsboro, MO
74 mi away
Fair Deal

$18,991

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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
67,690
Stock #:
68914K
VIN:
1GCPYCEF9MZ232488
Summit White 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

Sponsored Listing

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,690 mi

Bonne Terre, MO
58 mi away
Fair Deal

$34,609

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
Transmission:
6-Speed Automatic Overdrive
Mileage:
84,839
Stock #:
MX4469
VIN:
1GCPYCEF2LZ149662
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 mi

Home delivery from Louisville, TN
Price includes $592 shipping
Good Deal

$30,068

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:
Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
55,339
Stock #:
MX4446
VIN:
1GCPYCEL1MZ352307
Gray 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,339 mi

Home delivery from Louisville, TN
Price includes $592 shipping
Great Deal

$35,068

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
Transmission:
6-Speed Automatic Overdrive
Mileage:
58,190
Stock #:
B0579
VIN:
1GCRYCEF0LZ154111
Black 2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive
New arrival

 

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

58,190 mi

Benton, KY
81 mi away
Fair Deal

$30,724

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Northsky Blue Metallic
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
71,526
Stock #:
53595
VIN:
1GCPYCEK6NZ234598
Northsky Blue Metallic 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,526 mi

Home delivery from Cambridge, OH
Price includes $352 shipping
Great Deal

$30,278

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:
Automatic
Mileage:
116,709
Stock #:
D11212
VIN:
3GCPYCEFXKG115726
Black 2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,709 mi

Home delivery from Mt Juliet, TN
Price includes $292 shipping
Great Deal

$23,682

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:
123,697
Stock #:
C18221
VIN:
3GCPDCED3NG518221
White 2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive

 

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

123,697 mi

Home delivery from Athens, TN
Price includes $465 shipping
Fair Deal

$27,965

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:
85,808
Stock #:
16044
VIN:
1GCRYCEF3KZ315436
Black 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

85,808 mi

Home delivery from Dayton, OH
Price includes $513 shipping
Good Deal

$27,959

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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
67,690
Stock #:
68914K
VIN:
1GCPYCEF9MZ232488
Summit White 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,690 mi

Bonne Terre, MO
58 mi away
Fair Deal

$34,609

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:
10-Speed Automatic
Mileage:
16,913
Stock #:
R87954
VIN:
3GCUKCED9SG358155
Summit White 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 10-Speed Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,913 mi

Herculaneum, MO
70 mi away
Fair Deal

$46,618

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:
77,725
Stock #:
P13746A
VIN:
3GCPDCEK4PG170463
Black 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,725 mi

Home delivery from Roswell, GA
Price includes $762 shipping
Good Deal

$34,502

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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
43,773
Stock #:
28792225
VIN:
3GCPKCEK1SG330099
Black 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

43,773 mi

Store transfer to O Fallon, IL
Price includes $299 shipping
Good Deal

$39,297

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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
18,571
Stock #:
UCP1784
VIN:
3GCPDCEK7RG246485
Glacier Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,571 mi

Home delivery from Carrollton, KY
Price includes $387 shipping
Good Deal

$41,002

Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Transmission:
6-Speed Automatic Overdrive
Mileage:
154,561
Stock #:
477242
VIN:
3GCPYCEH5MG477242
 2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

 

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

154,561 mi

Cadet, MO
73 mi away
Fair Deal

$23,559

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
Fuel type:
Gasoline
Mileage:
93,416
Stock #:
313326
VIN:
1GCRYCEF8KZ313326
Gray 2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Pickup Truck Four-Wheel Drive
New arrival

 

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

93,416 mi

Home delivery from Marietta, GA
Price includes $562 shipping
Fair Deal

$27,880

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:
Black
Transmission:
8-Speed Automatic
Mileage:
3,560
Stock #:
P25761
VIN:
3GCPKCEK0TG160125
Summit White 2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,560 mi

Home delivery from Scottsdale, AZ
Price includes $1,600 shipping
Fair Deal

$46,899

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Red
Fuel type:
Diesel
Interior color:
Black
Mileage:
110,590
Stock #:
301317
VIN:
3GCUDCE84PG301317
Red 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive
New arrival

 

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,590 mi

Home delivery from Euless, TX
Price includes $792 shipping
Great Deal

$29,787

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:
Black Gba
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black H0u
Transmission:
Automatic
Mileage:
14,857
Stock #:
GMT281B1
VIN:
3GCPKCEK7SG176837
Black Gba 2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,857 mi

Home delivery from Nitro, WV
Price includes $1,000 shipping
Fair Deal

$45,317

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:
Red Hot
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black Cloth
Transmission:
Automatic
Mileage:
16,535
Stock #:
B2922
VIN:
3GCPDCEK1PG168878
Red Hot 2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,535 mi

Granite City, IL
94 mi away
Good Deal
Manufacturer certified

$40,489

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