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

Home delivery from Deland, FL

$837/mo est.

Price includes $644 shipping

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:: Sterling Gray Metallic
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 12,642
Stock #:: G222732P
VIN:: 3GCUKCEDXSG222732

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,625 miles

$37,672

Home delivery from Louisville, TN

$729/mo est.

Price includes $716 shipping

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:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 39,625
Stock #:: MX4224
VIN:: 1GCPYCEL0NZ150219

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,434 miles

$48,295

Year:: 2026
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 3L I6 Diesel
Exterior color:: Sterling Gray Metallic
Combined gas mileage:: 22 MPG
Fuel type:: Diesel
Interior color:: Black
Transmission:: Automatic
Mileage:: 7,434
Stock #:: P8174
VIN:: 3GCUKCE87TG104688

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,254 miles

$41,374

Home delivery from LaGrange, GA

$780/mo est.

Manufacturer certified

Price includes $721 shipping

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:: Blue
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 15,254
Stock #:: P744
VIN:: 3GCPDCEK1RG292524

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,884 miles

$34,643

Home delivery from Washington, MI

$672/mo est.

Price includes $863 shipping

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:: Jet Black
Transmission:: Automatic
Mileage:: 50,884
Stock #:: 244226
VIN:: 1GCPYCEF6MZ244226

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,580 miles

$32,310

Home delivery from Louisville, TN

$631/mo est.

Price includes $716 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:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 60,580
Stock #:: MX4313
VIN:: 1GCPYCEF3KZ373280

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,502 miles

$37,987

Year:: 2024
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 3L I6 Diesel
Exterior color:: Summit White
Combined gas mileage:: 25 MPG
Fuel type:: Diesel
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 53,502
Stock #:: RG216132
VIN:: 3GCUDCE81RG216132

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

57,655 miles

$34,188

Home delivery from Woodinville, WA

$663/mo est.

Price includes $2,193 shipping

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:: Blue
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 57,655
Stock #:: P178900
VIN:: 1GCPYCEF3MZ178900

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,562 miles

$36,395

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 277 hp 3L I6 Diesel
Exterior color:: Glacier Blue Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 52,562
Stock #:: 8892A
VIN:: 3GCUDCETXNG576157

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

10,015 miles

$44,899

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:: Gray
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 10,015
Stock #:: RG112792
VIN:: 3GCUDCED9RG112792

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,618 miles

$32,397

Store transfer to Pensacola, FL

$628/mo est.

16 mi awayPrice includes $399 store transfer

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Gray
Interior color:: Black
Transmission:: Automatic
Mileage:: 56,618
Stock #:: 28377093
VIN:: 1GCPYCEK1NZ156618

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Home delivery from Dayton, OH

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

85,808 miles

$28,433

Fair Deal

$556/mo est.

Price includes $987 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:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 85,808
Stock #:: 16044
VIN:: 1GCRYCEF3KZ315436

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,825 miles

$24,750

Home delivery from West Palm Beach, FL

$484/mo est.

Price includes $752 shipping

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:: White
Combined gas mileage:: 17 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Black
Transmission:: Automatic
Mileage:: 67,825
Stock #:: G293416
VIN:: 3GCPYCEH5KG293416

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2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

81,995 miles

$27,250

Home delivery from West Palm Beach, FL

$533/mo est.

Price includes $752 shipping

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
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 81,995
Stock #:: Z249779
VIN:: 1GCRYCEF7LZ249779

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

185,399 miles

$20,528

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:: 185,399
Stock #:: 11U2738
VIN:: 3GCPYCEF9KG142738

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,596 miles

$36,129

Home delivery from Ozark, AL

$699/mo est.

Price includes $153 shipping

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:: Shadow Gray Metallic
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 60,596
Stock #:: UF2633
VIN:: 1GCPYCEL2NZ117108

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,709 miles

$23,966

Home delivery from Mt Juliet, TN

$468/mo est.

Price includes $578 shipping

Year:: 2019
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Black
Interior color:: Black
Transmission:: Automatic
Mileage:: 116,709
Stock #:: D11212
VIN:: 3GCPYCEFXKG115726

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Home delivery from Chattanooga, TN

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,872 miles

$45,190

Fair Deal

$852/mo est.

Price includes $800 shipping

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:: 29,872
Stock #:: T26472A
VIN:: 3GCUDCED5RG172679

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,869 miles

$47,098

Home delivery from Jacksonville, FL

$881/mo est.

Price includes $322 shipping

Year:: 2025
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:: 23 MPG
Fuel type:: Diesel
Interior color:: Black
Transmission:: Automatic
Mileage:: 1,869
Stock #:: NV3183
VIN:: 3GCUKCE82SG363183

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2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

53,186 miles

$28,839