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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Alpine, TN

162 results
Alpine, TN
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Mt. Juliet Chrysler Dodge Jeep

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,860 miles

$34,678

Great Deal
Mount Juliet, TN
77 mi away
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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
62,860
Stock number:
RDW2666
VIN:
3GCUDCED2PG323930

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,709 miles

$24,990

Fair Deal
Mt Juliet, TN
77 mi away
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 number:
D11212
VIN:
3GCPYCEFXKG115726

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

175,684 miles

$19,995

Good Deal
Louisville, TN
76 mi away
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:
Black
Transmission:
Automatic
Mileage:
175,684
Stock number:
C70118
VIN:
1GCPYCEF1KZ370118

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,462 miles

$36,899

Fair Deal
Certified Pre-Owned
Gallatin, TN
74 mi away
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:
Lakeshore Blue Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
56,462
Stock number:
F246912
VIN:
3GCPDCEK0RG246912

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,400 miles

$39,522

Good Deal
Madison, TN
86 mi away
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:
Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
48,400
Stock number:
RG108873
VIN:
3GCUDCED0RG108873

Preparing for a close up...

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,288 miles

$36,917

Good Deal
La Follette, TN
56 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:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
31,288
Stock number:
P8910
VIN:
1GCPYCEF0MZ419523

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,899 miles

$42,147

Great Deal
Store transfer to Knoxville, TN
468 mi away • Price includes $149 shipping Price includes $149 shipping
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:
White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
5,899
Stock number:
28455695
VIN:
3GCPKCEK0SG323144

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,308 miles

$42,187

Great Deal
Shelbyville, TN
93 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:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
13,308
Stock number:
13569
VIN:
3GCPKCEK9SG168528

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,237 miles

$45,377

Great Deal
Middlesboro, KY
82 mi away
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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
8,237
Stock number:
P1059M
VIN:
3GCUKCED8SG149893

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,593 miles

$41,826

Great Deal
Franklin, TN
98 mi away
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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
14,593
Stock number:
T1144844A
VIN:
3GCUDCED6RG340832

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,860 miles

$34,678

Great Deal
Mount Juliet, TN
77 mi away
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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
62,860
Stock number:
RDW2666
VIN:
3GCUDCED2PG323930

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

16,432 miles

$45,535

Good Deal
La Follette, TN
56 mi away
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:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
16,432
Stock number:
K823
VIN:
3GCUKCEDXSG199128

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

101,310 miles

$23,515

Good Deal
La Follette, TN
56 mi away
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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
101,310
Stock number:
P8994A
VIN:
1GCRYCEH4KZ262201

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2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,300 miles

$45,347

Great Deal
Store transfer to Knoxville, TN
599 mi away • Price includes $349 shipping Price includes $349 shipping
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:
Brown (Tan)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
6,300
Stock number:
28249598
VIN:
3GCPKCEK1TG122953

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

101,310 miles

$23,515

Good Deal
La Follette, TN
56 mi away
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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
101,310
Stock number:
P8994A
VIN:
1GCRYCEH4KZ262201

Sponsored

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