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

141 results
Roby, MO
2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Thompson Buick GMC of Springfield

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,596 miles

$42,641

Good Deal
Certified Pre-Owned
Springfield, MO
69 mi away
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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
9,596
Stock number:
TU401764A
VIN:
3GCPKCEK5SG248408

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,288 miles

$31,611

Fair Deal
Bonne Terre, MO
91 mi away
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
Exterior color:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
75,288
Stock number:
68738K
VIN:
1GCPYCEH0MZ284173

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

127,149 miles

$26,995

Fair Deal
Sullivan, MO
71 mi away
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:
Silver Ice Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
127,149
Stock number:
F25368A
VIN:
1GCPYCEF9MZ169148

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

127,149 miles

$26,995

Fair Deal
Sullivan, MO
71 mi away
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:
Silver Ice Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
127,149
Stock number:
F25368A
VIN:
1GCPYCEF9MZ169148

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,961 miles

$35,322

Great Deal
Certified Pre-Owned
Springfield, MO
70 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
60,961
Stock number:
PG323530
VIN:
3GCUDCE84PG323530

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,075 miles

$28,718

Fair Deal
Reeds Spring, MO
90 mi away
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
99,075
Stock number:
13727A
VIN:
1GCPYCEFXMZ373828

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,288 miles

$31,611

Fair Deal
Bonne Terre, MO
91 mi away
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
Exterior color:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
75,288
Stock number:
68738K
VIN:
1GCPYCEH0MZ284173

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,273 miles

$39,996

Great Deal
Certified Pre-Owned
Springfield, MO
70 mi away
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, Cloth seat trim
Transmission:
Automatic
Mileage:
36,273
Stock number:
RG377384
VIN:
3GCUDCE8XRG377384

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

22,161 miles

$43,996

Fair Deal
Aurora, MO
97 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
22,161
Stock number:
TZ178355A
VIN:
3GCUDCE86RG328778

Sponsored

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