Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Upton, KY

195 results

Compare cars

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

180,190 miles

$20,985

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:: 180,190
Stock #:: ZT24431A
VIN:: 1GCPYCEF8MZ406678

Sponsored by Uebelhor & Sons Chevrolet Cadillac

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,224 miles

$29,574

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:: Silver Ice Metallic
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic
Mileage:: 80,224
Stock #:: CHC444
VIN:: 1GCPYCEF9KZ341112

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,657 miles

$34,198

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:: 74,657
Stock #:: 9537
VIN:: 3GCPDCEK4NG635014

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

10,616 miles

$47,743

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:: Automatic
Mileage:: 10,616
Stock #:: 29156A
VIN:: 3GCUKCED2SG358711

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,773 miles

$26,185

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:: NORTHSKY BLUE METALLIC
Fuel type:: Gasoline
Mileage:: 110,773
Stock #:: 26601A
VIN:: 3GCPYCEFXKG292258

Home delivery

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,580 miles

$32,195

Good Deal

$629/mo est.

Home delivery from Louisville, TN

Price includes $275 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

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,884 miles

$34,175

Good Deal

$663/mo est.

Home delivery from Washington, MI

Price includes $395 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

Home delivery

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,552 miles

$31,487

Fair Deal

$615/mo est.

Home delivery from Cincinnati, OH

Price includes $300 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,571 miles

$40,615

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:: Glacier Blue Metallic
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 18,571
Stock #:: UCP1784
VIN:: 3GCPDCEK7RG246485

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,365 miles

$37,067

Fair Deal

$718/mo est.

Home delivery from Middlesboro, KY

Price includes $268 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:: Gideon/Very Dark Atmosphere
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 46,365
Stock #:: P1208
VIN:: 1GCPYCEF9MZ293789

Preparing for a close up...

Photos coming soon

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

28,679 miles

$37,457

Great Deal

$713/mo est.

Home delivery from Mount Orab, OH

Price includes $507 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

Preparing for a close up...

Photos coming soon

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,373 miles

$38,609

Fair Deal

$748/mo est.

Home delivery from Smithville, TN

Price includes $600 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:: Northsky Blue Metallic
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 31,373
Stock #:: P1026
VIN:: 1GCPYCEF7MZ409278

Preparing for a close up...

Photos coming soon

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,725 miles

$34,746

Good Deal

$660/mo est.

Home delivery from Roswell, GA

Price includes $506 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:: 77,725
Stock #:: P13746A
VIN:: 3GCPDCEK4PG170463

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,115 miles

$32,400

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:: Black
Transmission:: 8-Speed Automatic
Mileage:: 48,115
Stock #:: 605420
VIN:: 3GCPDCEK8NG605420

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,457 miles

$37,381

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:: Dark Ash Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 42,457
Stock #:: PT7518
VIN:: 3GCUDCET8NG648487

Preparing for a close up...

Photos coming soon

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,169 miles

$31,815

Great Deal

$616/mo est.

Home delivery from Louisville, TN

Price includes $275 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

Preparing for a close up...

Photos coming soon

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,322 miles

$40,072

Great Deal

$763/mo est.

Home delivery from Arlington, TX

Price includes $1,070 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

Preparing for a close up...

Photos coming soon

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

110,590 miles

$31,056

Great Deal

$591/mo est.

Home delivery from Euless, TX

Price includes $1,060 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

Preparing for a close up...

Photos coming soon

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,839 miles

$28,565

Good Deal

$559/mo est.

Home delivery from Michigan Center, MI

Price includes $614 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

Preparing for a close up...

Photos coming soon

Home delivery

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

43,844 miles

$39,935

Great Deal

$754/mo est.

Home delivery from Kernersville, NC

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:: Black
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 43,844
Stock #:: 261432A
VIN:: 3GCUDCED2RG320299

Preparing for a close up...

Photos coming soon

Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,258 miles

$37,674

Fair Deal

$717/mo est.

Home delivery from Unadilla, GA

Price includes $573 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:: 55,258
Stock #:: P1926
VIN:: 3GCPDCEK3PG208734

Preparing for a close up...

Photos coming soon

Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,526 miles

$30,219

Great Deal

$585/mo est.

Home delivery from Cambridge, OH

Price includes $221 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

Preparing for a close up...

Photos coming soon

Home delivery

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,967 miles

$39,338

Great Deal

$743/mo est.

Home delivery from Mooresville, IN

Price includes $149 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

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,092 miles

$48,989

Fair Deal

$918/mo est.

Manufacturer certified

Jasper, IN

84 mi away

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:: Black
Transmission:: Automatic
Mileage:: 1,092
Stock #:: ZT24545A
VIN:: 3GCUKCED4SG296812

A better way to discover your best deal

Let us help you find a car you’ll love.

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Upton, KY

2021 Chevrolet Silverado 1500

$20,985

2019 Chevrolet Silverado 1500

$29,574

2022 Chevrolet Silverado 1500

$34,198

2025 Chevrolet Silverado 1500

$47,743

2019 Chevrolet Silverado 1500

$26,185

2019 Chevrolet Silverado 1500

$32,195

2021 Chevrolet Silverado 1500

$34,175

2019 Chevrolet Silverado 1500

$31,487

2024 Chevrolet Silverado 1500

$40,615

2021 Chevrolet Silverado 1500

$37,067

2023 Chevrolet Silverado 1500

$37,457

2021 Chevrolet Silverado 1500

$38,609

2023 Chevrolet Silverado 1500

$34,746

2022 Chevrolet Silverado 1500

$32,400

2022 Chevrolet Silverado 1500

$37,381

2021 Chevrolet Silverado 1500

$31,815

2023 Chevrolet Silverado 1500

$40,072

2023 Chevrolet Silverado 1500

$31,056

2020 Chevrolet Silverado 1500

$28,565

2024 Chevrolet Silverado 1500

$39,935

2023 Chevrolet Silverado 1500

$37,674

2022 Chevrolet Silverado 1500

$30,219

2024 Chevrolet Silverado 1500

$39,338

2025 Chevrolet Silverado 1500

$48,989

Popular Trims

Shop By City

Related Searches

Shop By Year

Popular Searches

Chevrolet dealers near Upton

A better way to discover your best deal