Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Montgomery, IL

$789/mo est.

Manufacturer certified

Fox Lake, IL

48 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
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 20,860
Stock #:: 50003A
VIN:: 3GCPKCEK1SG296827

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,075 miles

$40,569

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:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 20,075
Stock #:: 260201A
VIN:: 3GCPDCEK6RG209699

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,860 miles

$42,110

$789/mo est.

Manufacturer certified

Fox Lake, IL

48 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
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 20,860
Stock #:: 50003A
VIN:: 3GCPKCEK1SG296827

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,290 miles

$34,163

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Red
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 58,290
Stock #:: P1836
VIN:: 3GCPYCEK8NG208262

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,580 miles

$32,762

Home delivery from Louisville, TN

$640/mo est.

Price includes $842 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,884 miles

$34,066

Home delivery from Washington, MI

$661/mo est.

Price includes $286 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

72,552 miles

$31,715

Home delivery from Cincinnati, OH

$620/mo est.

Price includes $528 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:: Blue
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 72,552
Stock #:: C39198
VIN:: 3GCPYCEFXKG234862

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

28,679 miles

$37,915

Home delivery from Mount Orab, OH

$721/mo est.

Price includes $965 shipping

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:: Summit White
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 28,679
Stock #:: 5AT-010
VIN:: 3GCPDCEK7PG202581

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,169 miles

$32,382

Home delivery from Louisville, TN

$627/mo est.

Price includes $842 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:: Brown
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 69,169
Stock #:: MD2611
VIN:: 1GCPYCEF8MZ358258

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,678 miles

$38,589

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:: Summit White
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 45,678
Stock #:: P6036
VIN:: 3GCUDCED1PG323353

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,322 miles

$40,184

Home delivery from Arlington, TX

$765/mo est.

Price includes $1,182 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:: Gray
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 26,322
Stock #:: 48208
VIN:: 3GCUDCED4PG360459

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,590 miles

$31,166

Home delivery from Euless, TX

$594/mo est.

Price includes $1,172 shipping

Year:: 2023
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 3L I6 Diesel
Exterior color:: Red
Fuel type:: Diesel
Interior color:: Black
Mileage:: 110,590
Stock #:: 301317
VIN:: 3GCUDCE84PG301317

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 miles

$28,327

Home delivery from Michigan Center, MI

$554/mo est.

Price includes $376 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:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 84,839
Stock #:: MX4469
VIN:: 1GCPYCEF2LZ149662

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

148,190 miles

$18,154

Home delivery from Fort Wayne, IN

$355/mo est.

Price includes $254 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:: White
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 148,190
Stock #:: 199543
VIN:: 1GCRYCEF3KZ199543

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,075 miles

$40,569

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:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 20,075
Stock #:: 260201A
VIN:: 3GCPDCEK6RG209699

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,929 miles

$38,313

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
Transmission:: Automatic
Mileage:: 37,929
Stock #:: 26P3068
VIN:: 1GCPYCEL3NZ159500

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,788 miles

$34,284

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:: Summit White
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 54,788
Stock #:: P6106
VIN:: 3GCPYCEF6MG481122

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,526 miles

$30,276

Home delivery from Cambridge, OH

$586/mo est.

Price includes $278 shipping

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Northsky Blue Metallic
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 71,526
Stock #:: 53595
VIN:: 1GCPYCEK6NZ234598

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,083 miles

$36,995

$704/mo est.

Third-party certified

Frankfort, IL

30 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:: Summit White
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 51,083
Stock #:: 48816
VIN:: 3GCPDCEK7PG361519

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,534 miles

$29,602

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:: Gideon/Very Dark Atmosphere
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 101,534
Stock #:: 16P2279A
VIN:: 3GCPYCEFXMG121450

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,967 miles

$39,370

Home delivery from Mooresville, IN

$743/mo est.

Price includes $181 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:: Black
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 21,967
Stock #:: 13139
VIN:: 3GCPDCEK1RG293303

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,354 miles

$33,485

$648/mo est.

Elk Grove Village, IL

29 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:: Glacier Blue Metallic
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 81,354
Stock #:: N25159A
VIN:: 3GCPDCED6NG679176

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,295 miles

$38,776