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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Nappanee, IN

174 results
Nappanee, IN
2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Southwest Auto Sales

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

95,865 miles

$23,450

Fair Deal
Roanoke, IN
45 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
95,865
Stock number:
B1232
VIN:
1GCRYCEH2KZ223462

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,976 miles

$45,948

Fair Deal
Merrillville, IN
70 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:
11,976
Stock number:
H260466A
VIN:
3GCUKCED4SG213184

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,460 miles

$26,800

Great Deal
Merrillville, IN
69 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
84,460
Stock number:
8887A
VIN:
1GCPYCEH8MZ430612

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

90,496 miles

$29,995

Fair Deal
Allegan, MI
75 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:
90,496
Stock number:
BB5476A
VIN:
1GCPYCEF3MZ231546

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,975 miles

$32,049

Great Deal
Lafayette, IN
84 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
42,975
Stock number:
C129
VIN:
1GCPYCEF8LZ282796

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

42,862 miles

$29,533

Fair Deal
Archbold, OH
87 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
42,862
Stock number:
PC427057
VIN:
1GCRYCEF7KZ427057

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,460 miles

$27,500

Great Deal
Noblesville, IN
98 mi away
Year:
2020
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
72,460
Stock number:
213089
VIN:
1GCPYCEHXLZ213089

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,112 miles

$29,550

Good Deal
New Haven, IN
56 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Shadow Gray Metallic
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,112
Stock number:
NH0910A
VIN:
1GCPYCEK6NZ103509

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,988 miles

$44,677

Good Deal
Fort Wayne, IN
48 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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
8,988
Stock number:
P7880C
VIN:
3GCUKCED8SG112780

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,403 miles

$38,000

Good Deal
Defiance, OH
86 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:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
20,403
Stock number:
25G5296A
VIN:
3GCPDCEK5RG235209

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,704 miles

$31,500

Great Deal
Orland Park, IL
97 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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
50,704
Stock number:
B10901
VIN:
1GCPYCEF7MZ410785

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,243 miles

$39,900

Fair Deal
Bradley, IL
98 mi away
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 G7c
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black H0u
Transmission:
8-Speed Automatic
Mileage:
15,243
Stock number:
p3665
VIN:
3GCPDCEKXPG195562

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

95,865 miles

$23,450

Fair Deal
Roanoke, IN
45 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
95,865
Stock number:
B1232
VIN:
1GCRYCEH2KZ223462

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

42,862 miles

$29,533

Fair Deal
Archbold, OH
87 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
42,862
Stock number:
PC427057
VIN:
1GCRYCEF7KZ427057

Sponsored

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  5. / Indiana
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