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

$654/mo est.

Manufacturer certified

Madison, WI

8 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:: Northsky Blue Metallic
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 58,068
Stock #:: P20970
VIN:: 3GCPYCEF3MG481319

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,578 miles

$35,572

Home delivery from Pueblo, CO

$689/mo est.

Price includes $1,276 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

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

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,874 miles

$29,942

$586/mo est.

Manufacturer certified

Milwaukee, WI

80 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:: 74,874
Stock #:: C20052PC
VIN:: 1GCPYCEF4KZ376740

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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,286 miles

$26,560

Home delivery from Elmhurst, IL

$515/mo est.

Price includes $351 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

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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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

103,764 miles

$22,571

Home delivery from Ashland, KY

$442/mo est.

Price includes $1,446 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:: Northsky Blue Metallic
Combined gas mileage:: 17 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 103,764
Stock #:: K26201A
VIN:: 1GCRYCEH8KZ235938

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

123,861 miles

$24,886

Home delivery from New Haven, IN

$487/mo est.

Price includes $546 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:: 123,861
Stock #:: X0691A
VIN:: 1GCPYCEF5KZ262939

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

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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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

10,469 miles

$43,447

Store transfer to Madison, WI

$814/mo est.

4 mi awayPrice includes $449 store transfer

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:: Gray
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 10,469
Stock #:: 28399229
VIN:: 3GCPKCEK7SG292250

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

134,753 miles

$21,599

Home delivery from Mechanicsburg, PA

$423/mo est.

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

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,686 miles

$25,438

Home delivery from Clio, MI

$498/mo est.

Price includes $442 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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Home delivery from West Palm Beach, FL

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

93,755 miles

$24,689

Great Deal

$483/mo est.

Free home delivery

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:: Brown Metallic
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 93,755
Stock #:: PV106422
VIN:: 3GCPYCEF9LG106422

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

117,609 miles

$24,363

Home delivery from Maryland Heights, MO

$477/mo est.

Price includes $368 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:: Summit White
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 117,609
Stock #:: C260013T
VIN:: 1GCPYCEF6LZ197665

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,609 miles

$32,481

$630/mo est.

Manufacturer certified

Orfordville, WI

36 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:: Red Hot
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 65,609
Stock #:: 36620B
VIN:: 1GCPYCEFXMZ229163

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

122,179 miles

$22,569

Home delivery from Howell, MI

$442/mo est.

Price includes $574 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:: Cajun Red Tintcoat Gpj
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black H1t
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 122,179
Stock #:: KZ358984
VIN:: 1GCRYCEF7KZ358984

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,478 miles

$36,225