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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Doctors Inlet, FL

117 results
Doctors Inlet, FL
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Mazda of St. Augustine

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,395 miles

$27,888

Fair Deal
St. Augustine, FL
30 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
116,395
Stock number:
Z132702A
VIN:
1GCPYCEF5MZ250549

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,441 miles

$44,454

Fair Deal
Certified Pre-Owned
Macclenny, FL
24 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:
Red
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
9,441
Stock number:
203105
VIN:
3GCPKCEK1SG278988

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

124,481 miles

$23,611

Fair Deal
Jacksonville, FL
8 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:
124,481
Stock number:
KG126984
VIN:
3GCPYCEFXKG126984

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,395 miles

$27,888

Fair Deal
St. Augustine, FL
30 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
116,395
Stock number:
Z132702A
VIN:
1GCPYCEF5MZ250549

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

124,481 miles

$23,611

Fair Deal
Jacksonville, FL
8 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:
124,481
Stock number:
KG126984
VIN:
3GCPYCEFXKG126984

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,457 miles

$26,300

Great Deal
Jacksonville, FL
18 mi away
Year:
2022
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:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
116,457
Stock number:
20623
VIN:
3GCPDCED7NG500143

Preparing for a close up...

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,237 miles

$31,872

Good Deal
Jacksonville, FL
22 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
60,237
Stock number:
AY22879
VIN:
3GCPYCEK2NG147393

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Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,247 miles

$44,347

Fair Deal
Store transfer to Jacksonville, FL
449 mi away • Price includes $349 shipping Price includes $349 shipping
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
White
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
26,247
Stock number:
27756082
VIN:
3GCUDCE81RG151606

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,490 miles

$40,447

Fair Deal
Store transfer to Jacksonville, FL
519 mi away • Price includes $449 shipping Price includes $449 shipping
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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,490
Stock number:
28011249
VIN:
3GCUDCED2PG312359

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,906 miles

$41,720

Good Deal
Jacksonville, FL
8 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:
Black
Transmission:
Automatic
Mileage:
24,906
Stock number:
RG433940P
VIN:
3GCUDCED3RG433940

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Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,791 miles

$41,634

Fair Deal
Jacksonville, FL
15 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
49,791
Stock number:
128259C
VIN:
3GCUDCED5RG128259

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Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,441 miles

$44,454

Fair Deal
Certified Pre-Owned
Macclenny, FL
24 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:
Red
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
9,441
Stock number:
203105
VIN:
3GCPKCEK1SG278988

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,031 miles

$44,500

Fair Deal
Atlantic Beach, FL
27 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:
Cypress Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
5,031
Stock number:
T6656
VIN:
3GCPKCEK8SG329371

Sponsored

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