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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Tutor Key, KY

194 results
Tutor Key, KY
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD McFarland Chevrolet Buick

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,080 miles

$41,750

Good Deal
Maysville, KY
78 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:
Black
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Transmission:
Automatic
Mileage:
34,080
Stock number:
T175637
VIN:
3GCUDCE80RG175637

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

61,565 miles

$28,955

Fair Deal
Lexington, KY
93 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:
Red
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
61,565
Stock number:
257120
VIN:
1GCRYCEF7KZ279394

Sponsored

2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

2,221 miles

$51,976

Fair Deal
Nitro, WV
64 mi away
Year:
2026
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 Gba
Fuel type:
Gasoline
Interior color:
Jet Black H0u
Transmission:
Automatic
Mileage:
2,221
Stock number:
GMT127B
VIN:
3GCUKCED1TG146755

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,518 miles

$29,895

Great Deal
Nicholasville, KY
98 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:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
69,518
Stock number:
NG192327
VIN:
3GCPYCEK5NG192327

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,865 miles

$38,620

Good Deal
Lexington, KY
95 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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
23,865
Stock number:
N8897
VIN:
3GCPDCEK7RG398038

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,335 miles

$32,474

Great Deal
South Charleston, WV
67 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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
40,335
Stock number:
D26C43338A
VIN:
1GCPYCEH8MZ392170

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,176 miles

$43,000

Good Deal
Maysville, KY
78 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:
14,176
Stock number:
T342503
VIN:
3GCUDCED8RG342503

Sponsored

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  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Kentucky
  6. / Tutor Key
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