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

123 results

Sort by:

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,725 miles

$37,990

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
Transmission:: Automatic
Mileage:: 8,725
Stock #:: 147838
VIN:: 3GCPDCEK5PG147838

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,051 miles

$39,999

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:: 27,051
Stock #:: H1358
VIN:: 3GCPDCEK2PG122489

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,735 miles

$33,995

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:: Custom Trailboss
Transmission:: 8-Speed Automatic
Mileage:: 42,735
Stock #:: EG10839A
VIN:: 3GCPDCEK4NG614132

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,272 miles

$33,000

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:: Northsky Blue Metallic
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic
Mileage:: 46,272
Stock #:: C15222
VIN:: 1GCPYCEF5LZ352058

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,195 miles

$32,990

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:: Summit White
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 44,195
Stock #:: C14811
VIN:: 3GCPYCEK3NG116041

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

130,739 miles

$19,600

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
Transmission:: Automatic
Mileage:: 130,739
Stock #:: 404764
VIN:: 1GCRYCEF5KZ404764

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,725 miles

$37,990

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
Transmission:: Automatic
Mileage:: 8,725
Stock #:: 147838
VIN:: 3GCPDCEK5PG147838

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,957 miles

$34,890

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
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic
Mileage:: 41,957
Stock #:: C15255
VIN:: 1GCPYCEF5MZ265942

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

124,735 miles

$21,995

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:: Automatic
Mileage:: 124,735
Stock #:: 13438
VIN:: 1GCPYCEF0KZ378338

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,051 miles

$32,980

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:: Black
Transmission:: Automatic
Mileage:: 58,051
Stock #:: 111-26-128T
VIN:: 1GCPYCEH9MZ433518

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,008 miles

$41,500

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:: 32,008
Stock #:: R6927A
VIN:: 3GCUDCED7PG214993

Preparing for a close up...

Photos coming soon

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

119,818 miles

$24,174

Good Deal

$473/mo est.

Home delivery from Schenectady, NY

Price includes $178 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
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 119,818
Stock #:: 224999
VIN:: 3GCPYCEF7LG224999

Preparing for a close up...

Photos coming soon

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

134,753 miles

$21,599

Good Deal

$423/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:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 134,753
Stock #:: 278503A
VIN:: 1GCPYCEH0LZ278503

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,912 miles

$32,890

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:: Shadow Gray Metallic
Combined gas mileage:: 16 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 59,912
Stock #:: J15381A
VIN:: 1GCPYCEH4MZ380503

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,051 miles

$39,999

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:: 27,051
Stock #:: H1358
VIN:: 3GCPDCEK2PG122489

Preparing for a close up...

Photos coming soon

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,470 miles

$23,594

Good Deal

$458/mo est.

Home delivery from Stafford, VA

Price includes $598 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
Fuel type:: Gasoline
Interior color:: Gray
Mileage:: 133,470
Stock #:: DMV1729
VIN:: 3GCPYCEF1MG260401

Preparing for a close up...

Photos coming soon

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,169 miles

$34,104

Fair Deal

$662/mo est.

Home delivery from Louisville, TN

Price includes $1,436 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,809 miles

$38,995

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:: 32,809
Stock #:: GM3743
VIN:: 1GCPYCEL9NZ176799

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

88,915 miles

$29,999

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:: Dark Ash Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 88,915
Stock #:: A25720A
VIN:: 3GCPDCEK7NG684420

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,830 miles

$31,995

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:: Shadow Gray Metallic
Fuel type:: Flex Fuel Vehicle
Interior color:: Jet Black
Transmission:: 6-Speed Automatic
Mileage:: 47,830
Stock #:: R10246A
VIN:: 1GCPYCEH4KZ400584

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

94,125 miles

$28,475

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:: 94,125
Stock #:: W26721B
VIN:: 3GCPYCEF7KG106160

Preparing for a close up...

Photos coming soon

Home delivery

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

93,755 miles

$24,689

Great Deal

$483/mo est.

Home delivery from West Palm Beach, FL

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

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,079 miles

$35,324

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:: 39,079
Stock #:: B8020
VIN:: 3GCPDCEK4NG540095

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

130,739 miles

$19,600

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
Transmission:: Automatic
Mileage:: 130,739
Stock #:: 404764
VIN:: 1GCRYCEF5KZ404764

A better way to discover your best deal

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