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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near De Winton, AB

36 results
Calgary, AB
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Shaganappi GM

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,584 kilometres

$41,911

Good Deal
Certified Pre-Owned
Calgary, AB
26 km 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 colour:
Gray (Slate Grey Metallic)
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
104,584
Stock number:
UP7553
VIN:
3GCUDCED0RG131442

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

61,927 kilometres

$41,155

Good Deal
Calgary, AB
12 km 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
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
61,927
Stock number:
PU2060
VIN:
3GCPDCEK6PG296677

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

129,720 kilometres

$39,999

Good Deal
Calgary, AB
16 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Silver
Transmission:
Automatic
Mileage:
129,720
Stock number:
179960
VIN:
3GCUDCED9RG179960

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

12,538 kilometres

$54,104

Good Deal
Airdrie, AB
44 km 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
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
12,538
Stock number:
CNR8474A
VIN:
3GCUKCED7SG258474

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,616 kilometres

$47,709

Good Deal
Certified Pre-Owned
Calgary, AB
15 km 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 colour:
White
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
47,616
Stock number:
SGR6489A
VIN:
3GCUDCED2RG146489

Preparing for a close up...

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

139,637 kilometres

$37,995

Good Deal
Calgary, AB
22 km 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 colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
139,637
Stock number:
156335
VIN:
3GCUDCED3RG156335

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

61,927 kilometres

$41,155

Good Deal
Calgary, AB
12 km 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
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
61,927
Stock number:
PU2060
VIN:
3GCPDCEK6PG296677

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

242,041 kilometres

$22,990

Good Deal
Calgary, AB
16 km 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 colour:
White
Combined gas mileage:
15 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
242,041
Stock number:
266797
VIN:
1GCPYCEF9KZ266797

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,584 kilometres

$41,911

Good Deal
Certified Pre-Owned
Calgary, AB
26 km 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 colour:
Gray (Slate Grey Metallic)
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
104,584
Stock number:
UP7553
VIN:
3GCUDCED0RG131442

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

129,720 kilometres

$39,999

Good Deal
Calgary, AB
16 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Silver
Transmission:
Automatic
Mileage:
129,720
Stock number:
179960
VIN:
3GCUDCED9RG179960

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

166,367 kilometres

$29,995

Good Deal
Calgary, AB
22 km 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 colour:
Gray
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
166,367
Stock number:
111419
VIN:
3GCPYCEK1NG111419

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

151,635 kilometres

$34,995

Fair Deal
Calgary, AB
12 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
151,635
Stock number:
543602
VIN:
3GCPDCED8NG543602

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

147,209 kilometres

$38,900

Fair Deal
Calgary, AB
19 km 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 colour:
Gray
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
147,209
Stock number:
CGP9708A
VIN:
3GCUDCEDXPG279708

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,970 kilometres

$46,900

Fair Deal
Calgary, AB
19 km 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 colour:
White
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
23,970
Stock number:
CGR6189A
VIN:
3GCUDCED7PG256189

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Alberta
  6. / De Winton
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