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

224 results
Chattanooga, TN
2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Motorpoint Roswell

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

142,629 miles

$21,786

Great Deal
Roswell, GA
88 mi away
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
142,629
Stock number:
224246
VIN:
3GCPYCEF2LG224246

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,360 miles

$35,034

Good Deal
Alpharetta, GA
89 mi away
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:
Red
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
49,360
Stock number:
P6636
VIN:
1GCPYCEL1MZ206649

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,008 miles

$34,999

Fair Deal
Atlanta, GA
97 mi away
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
Fuel type:
Gasoline
Mileage:
73,008
Stock number:
T16032A
VIN:
3GCPYCEL2MG440475

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,558 miles

$43,877

Good Deal
Guntersville, AL
79 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:
4,558
Stock number:
C2579A
VIN:
3GCPKCEK1SG145745

2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

74,925 miles

$27,761

Great Deal
Louisville, TN
90 mi away
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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
74,925
Stock number:
MX2879
VIN:
1GCRYCEFXLZ100847

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

115,016 miles

$26,808

Good Deal
Chattanooga, TN
3 mi away
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 (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
115,016
Stock number:
35745P
VIN:
1GCPYCEF5LZ200653

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,590 miles

$42,999

Great Deal
Certified Pre-Owned
Arab, AL
88 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:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
20,590
Stock number:
26-127A
VIN:
3GCUDCED3RG215772

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,668 miles

$26,950

Great Deal
Murfreesboro, TN
85 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
76,668
Stock number:
512523
VIN:
3GCPYCEF5KG227446

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,058 miles

$37,950

Fair Deal
Gainesville, GA
96 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 (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
31,058
Stock number:
43970B
VIN:
3GCPYCEF6MG439761

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,263 miles

$40,974

Good Deal
Huntsville, AL
83 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:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
42,263
Stock number:
5T2895A
VIN:
3GCUDCED0RG314341

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,164 miles

$44,550

Good Deal
Dallas, GA
84 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
6,164
Stock number:
C02189
VIN:
3GCUDCED2RG344828

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,151 miles

$26,311

Great Deal
Arab, AL
88 mi away
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:
100,151
Stock number:
AF239
VIN:
3GCPYCEFXLG196177

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,944 miles

$31,597

Great Deal
Store transfer to Chattanooga, TN
1,816 mi away • Price includes $1,599 shipping Price includes $1,599 shipping
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:
Blue
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
42,944
Stock number:
28107840
VIN:
1GCPYCEF8KZ380239

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,272 miles

$34,899

Good Deal
Marietta, GA
91 mi away
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:
8-Speed Automatic
Mileage:
40,272
Stock number:
637025
VIN:
3GCPDCEK8NG637025

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,058 miles

$37,950

Fair Deal
Gainesville, GA
96 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 (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
31,058
Stock number:
43970B
VIN:
3GCPYCEF6MG439761

Sponsored

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