Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Madison, WI

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

97,541 miles

$28,092

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:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 97,541
Stock #:: 44P2297
VIN:: 1GCPYCEHXMZ381395

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2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,783 miles

$32,999

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:: 81,783
Stock #:: 46T667A
VIN:: 3GCUDCEDXRG126605

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,545 miles

$30,495

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:: Black
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 71,545
Stock #:: 26300A
VIN:: 3GCPYCEK5NG116803

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,545 miles

$30,495

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:: Black
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 71,545
Stock #:: 26300A
VIN:: 3GCPYCEK5NG116803

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,162 miles

$30,988

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 (Satin Steel Metallic G9k)
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black H1t
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 80,162
Stock #:: 25085A
VIN:: 1GCPYCEF2LZ184766

Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,578 miles

$35,580

Fair Deal

$689/mo est.

Home delivery from Pueblo, CO

Price includes $1,286 shipping

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Blue Metallic
Interior color:: Black
Transmission:: Automatic
Mileage:: 34,578
Stock #:: P149631
VIN:: 1GCPYCEK2NZ149631

Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,286 miles

$27,830

Fair Deal

$539/mo est.

Home delivery from Elmhurst, IL

Price includes $330 shipping

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Gray (Steel Metallic)
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 98,286
Stock #:: 3632A
VIN:: 3GCPYCEK2NG153209

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

134,753 miles

$20,899

Good Deal

$409/mo est.

Home delivery from Mechanicsburg, PA

Free home delivery

Year:: 2020
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:: Shadow Gray Metallic
Combined gas mileage:: 16 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 134,753
Stock #:: 278503A
VIN:: 1GCPYCEH0LZ278503

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,599 miles

$41,700

Fair Deal

$794/mo est.

Home delivery from Ashland, OH

Price includes $800 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:: Black
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 13,599
Stock #:: D5861A
VIN:: 3GCPDCEK9PG299945

Home delivery

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,220 miles

$48,670

Fair Deal

$912/mo est.

Home delivery from Herculaneum, MO

Price includes $672 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:: Black
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 10-Speed Automatic
Mileage:: 6,220
Stock #:: T87306
VIN:: 3GCUKCED8SG344103

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,084 miles

$31,544

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Summit White
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 59,084
Stock #:: 49521A
VIN:: 3GCPYCEK2NG125426

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Home delivery

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,686 miles

$25,427

Good Deal

$498/mo est.

Home delivery from Clio, MI

Price includes $432 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:: Automatic
Mileage:: 108,686
Stock #:: 12242
VIN:: 1GCPYCEFXKZ379786

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

92,193 miles

$25,499

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:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 92,193
Stock #:: 184482
VIN:: 1GCRYCEF0KZ184482

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,170 miles

$36,144

Year:: 2021
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 420 hp 6.2L V8
Exterior color:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 47,170
Stock #:: PCP10136
VIN:: 3GCPYCELXMG167138

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

121,168 miles

$24,380

Year:: 2019
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 121,168
Stock #:: 46084A
VIN:: 1GCPYCEF6KZ266711

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

71,462 miles

$26,933

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:: 71,462
Stock #:: N02874
VIN:: 1GCRYCEF5KZ323618

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,445 miles

$42,444

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:: Jet Black
Transmission:: Automatic
Mileage:: 25,445
Stock #:: 14514A
VIN:: 3GCUDCED4RG109962

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Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,539 miles

$35,813

Fair Deal

$695/mo est.

Home delivery from Columbia, KY

Price includes $814 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:: Black
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 52,539
Stock #:: MZ197398
VIN:: 1GCPYCEF7MZ197398

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Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,478 miles

$36,224

Good Deal

$690/mo est.

Home delivery from Houston, TX

Price includes $1,225 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:: Dark Ash Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: Automatic
Mileage:: 70,478
VIN:: 3GCUDCED4PG189356

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Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,636 miles

$38,951

Fair Deal

$755/mo est.

Home delivery from Herculaneum, MO

Price includes $672 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:: Glacier Blue Metallic
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 10-Speed Automatic
Mileage:: 33,636
Stock #:: RK87237
VIN:: 3GCPDCED0NG666486

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,399 miles

$32,902

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
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 60,399
Stock #:: P14575
VIN:: 1GCPYCEF4LZ137240

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Home delivery

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,597 miles

$38,500

Good Deal

$727/mo est.

Home delivery from Mechanicsburg, PA

Free home delivery

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:: 47,597
Stock #:: 190358A
VIN:: 3GCUDCED9RG190358

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Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,123 miles

$37,082

Good Deal

$718/mo est.

Home delivery from Defiance, OH

Price includes $570 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:: Glacier Blue Metallic
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 30,123
Stock #:: G534770
VIN:: 3GCPDCED6NG534770

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,084 miles

$31,544

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Summit White
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 59,084
Stock #:: 49521A
VIN:: 3GCPYCEK2NG125426

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