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Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearWare, MA

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242 vehicles found

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:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black/Umber
Transmission:
Automatic
Mileage:
3,028
Stock #:
48578
VIN:
3GCUKFED4SG270700
Summit White 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Imperial Chevrolet

Sponsored by Imperial Chevrolet

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

3,028 mi

Mendon, MA
41 mi away
Good Deal

$56,467

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
96,722
Stock #:
C26355A
VIN:
1GCPYFED3MZ304317
Cherry Red Tintcoat 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

96,722 mi

Gardner, MA
24 mi away
Good Deal

$32,484

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,422
Stock #:
LG204779
VIN:
3GCPYFED3LG204779
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,422 mi

Auburn, MA
23 mi away
Good Deal
Third-party certified

$36,448

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
83,685
Stock #:
227612
VIN:
1GCUYFET9NZ227612
Black 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

83,685 mi

Home delivery from Baton Rouge, LA
Price includes $1,712 shipping
Fair Deal

$36,636

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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
117,452
Stock #:
16521V
VIN:
1GCPYFEDXKZ212313
Summit White 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

117,452 mi

Hartford, CT
39 mi away
Great Deal

$25,593

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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
39,308
Stock #:
28955807
VIN:
3GCUDFED9PG309119
Black 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

39,308 mi

Store transfer to Westborough, MA
Price includes $899 shipping
Good Deal

$44,897

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:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
66,475
Stock #:
210668A
VIN:
3GCPYFEDXKG178566
Black 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

66,475 mi

Willimantic, CT
39 mi away
Fair Deal

$33,851

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:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
55,930
Stock #:
C26326A
VIN:
3GCUDFED5PG268195
Sterling Gray Metallic 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

55,930 mi

Gardner, MA
24 mi away
Good Deal

$42,464

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray (Satin Steel Metallic)
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
25,029
Stock #:
S3991A
VIN:
1GCPYFED0NZ115366
Gray (Satin Steel Metallic) 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

25,029 mi

Woonsocket, RI
45 mi away
Fair Deal

$43,899

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:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
113,924
Stock #:
AB7473A
VIN:
1GCPYFED9KZ165629
Shadow Gray Metallic 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic
Price drop

-$1,000

 

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

113,924 mi

Westborough, MA
35 mi away
Great Deal

$25,395

$24,395

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
96,486
Stock #:
5839
VIN:
1GCPYFED1LZ137843
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

96,486 mi

Fitchburg, MA
33 mi away
Fair Deal

$30,474

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:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
41,586
Stock #:
NT26107A
VIN:
3GCUDFED6RG237752
Slate Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

41,586 mi

Home delivery from Delphos, OH
Price includes $790 shipping
Good Deal

$46,715

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:
Jet Black
Transmission:
Automatic
Mileage:
110,296
Stock #:
C26258A
VIN:
3GCUDFED5PG276488
Dark Ash Metallic 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

110,296 mi

Gardner, MA
24 mi away
Fair Deal

$35,272

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
70,157
Stock #:
AB7708A
VIN:
1GCPYFED6LZ309459
Summit White 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$808

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

70,157 mi

Westborough, MA
35 mi away
Good Deal

$34,483

$33,675

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
96,722
Stock #:
C26355A
VIN:
1GCPYFED3MZ304317
Cherry Red Tintcoat 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

96,722 mi

Gardner, MA
24 mi away
Good Deal

$32,484

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Gray
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
75,314
Stock #:
G115624
VIN:
3GCUDFE81PG115624
Gray 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

75,314 mi

Home delivery from Houston, TX
Price includes $2,334 shipping
Good Deal

$39,057

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,422
Stock #:
LG204779
VIN:
3GCPYFED3LG204779
Black 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,422 mi

Auburn, MA
23 mi away
Good Deal
Third-party certified

$36,448

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:
Automatic
Mileage:
41,648
Stock #:
PM238331
VIN:
1GCPYFEL5NZ238331
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

41,648 mi

Home delivery from Pleasantville, NJ
Price includes $408 shipping
Great Deal

$37,298

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
Fuel type:
Gasoline
Interior color:
Black
Mileage:
96,707
Stock #:
CT11901
VIN:
1GCPYFED0LZ340593
Gray 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

96,707 mi

Manchester, CT
39 mi away
Good Deal

$26,949

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
75,412
Stock #:
390926
VIN:
3GCPYFED7MG390926
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

75,412 mi

Home delivery from Fort Montgomery, NY
Price includes $278 shipping
Great Deal

$33,172

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:
40,099
Stock #:
STK100848
VIN:
3GCUDFED3RG100848
Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,050

 

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

40,099 mi

Home delivery from Westfield, IN
Price includes $739 shipping
Good Deal

$47,288

$46,238

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
65,878
Stock #:
VC26145
VIN:
3GCPYFEDXMG436331
Northsky Blue Metallic 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,878 mi

Home delivery from Hicksville, OH
Price includes $805 shipping
Good Deal

$36,830

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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
70,157
Stock #:
AB7708A
VIN:
1GCPYFED6LZ309459
Summit White 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$808

Sponsored Listing

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

70,157 mi

Westborough, MA
35 mi away
Good Deal

$34,483

$33,675

Overview

The Chevrolet Silverado 1500 LT Trail Boss is only available from in two body configurations: the Crew Cab Short Bed and the Crew Cab Standard Bed. As the “Trail Boss” name suggests, this trim is only available in four-wheel drive. From there, the powertrain options get a little dizzying. You have four engines to choose from: The 2.7-liter turbocharged four-cylinder, the 5.3-liter EcoTec V-8, the 3.0-liter Duramax Turbo Diesel inline six, and the 6.2-liter EcoTec V-8. The four-cylinder turbo is the only one available with an eight-speed automatic transmission. All of the other engines require the 10-speed automatic.

Key Features

  • Standard 355hp 5.3-liter V-8 standard, standard 10-speed automatic transmission
  • Two-inch factory suspension lift, 18-inch gloss black wheels, Goodyear Wrangler Duratrac tires, raised hood and styled insert
  • Leather-wrapped wheel, remote start, all-weather floor liners, 40/20/40 split bench seat, dual-zone climate control, 10-way power driver’s seat, heated front seats, heated wheel
  • 13.4-inch color touchscreen display, 12.3-inch multicolor, reconfigurable Driver Information Center, 6-speaker audio, WiFi hot spot, Wireless Apple CarPlay/Android Auto

Pricing Details

The Chevrolet Silverado LT Trail Boss has a base MSRP of $57,095 with the turbocharged four-cylinder. Used examples on CarGurus range from $24,042.00 to $76,717.75 with an average price of $30,150.03. The 5.3-liter V-8 adds $2,315, the diesel engine adds $3,130 and the 6.2-liter V-8 adds $4,460. There are nine different option packages, ranging from $325 for the Dark Essentials Package, to the $3,685 LT Trail Boss Premium Package, which includes Convenience Package II, Safety Package, Bed Protection Package, a power up and down tailgate and leather upholstery.

Specifications

Performance

  • Engine

    355hp 5.3-liter V8

  • Transmission

    10-speed automatic

  • Drivetrain

    Four-wheel drive

  • Horsepower/Torque

    355hp/383 lb-ft

  • 0-60 mph

    15.1 seconds (estimated)

  • MPG

    15 mpg city, 19 highway, 16 combined

  • Curb weight

    5,130 pounds

Dimensions

  • wheelbase

    147.4 inches

  • length

    231.9 inches

  • width

    81.2 inches

  • height

    75.5 inches

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