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Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearChester, NY

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271 vehicles found

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
Freedom Chevrolet

Sponsored by Freedom Chevrolet

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

75,412 mi

Fort Montgomery, NY
14 mi away
Great Deal

$32,994

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:
Gideon/Very Dark Atmosphere
Transmission:
8-Speed Automatic
Mileage:
59,246
Stock #:
195928
VIN:
3GCPYFED4KG195928
Summit White 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

Sponsored Listing

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,246 mi

Fort Montgomery, NY
14 mi away
Good Deal

$34,294

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:
56,370
Stock #:
Z4372
VIN:
3GCUDFEDXRG251878
Summit White 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

56,370 mi

Brookfield, CT
45 mi away
Good Deal

$44,992

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:
Glacier Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
35,710
Stock #:
25097P
VIN:
3GCPDFEK0NG606837
Glacier Blue Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 8-Speed Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

35,710 mi

New Canaan, CT
42 mi away
Good Deal
Manufacturer certified

$40,216

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:
Automatic
Mileage:
47,594
Stock #:
S19594A
VIN:
1GCPYFEL6NZ218377
Northsky Blue Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,594 mi

Home delivery from Newton, NC
Price includes $818 shipping
Fair Deal

$40,816

Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
80,952
Stock #:
323297
VIN:
3GCUDFE80PG323297
Silver 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

80,952 mi

Home delivery from Baton Rouge, LA
Price includes $1,555 shipping
Fair Deal

$38,379

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:
White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
49,611
Stock #:
28765309
VIN:
3GCPKFEK6SG208193
White 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

49,611 mi

Store transfer to Wayne, NJ
Price includes $1,799 shipping
Good Deal

$43,797

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black Leather Appoint
Transmission:
Automatic
Mileage:
44,561
Stock #:
6882U
VIN:
3GCPYFEL7NG100113
Summit White 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

44,561 mi

Wilton, CT
45 mi away
Great Deal
Manufacturer certified

$39,995

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:
Blue
Fuel type:
Gasoline
Interior color:
Black
Mileage:
66,901
Stock #:
XWG-LZ189605
VIN:
1GCPYFED3LZ189605
Blue 2020 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive

 

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

66,901 mi

Elizabeth, NJ
48 mi away
Great Deal

$30,985

Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Black
Combined gas mileage:
23 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
21,860
Stock #:
66281A
VIN:
3GCUKFE80SG166157
Black 2025 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

21,860 mi

Englewood, NJ
36 mi away
Fair Deal

$51,995

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:
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

-$870

 

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

113,924 mi

Home delivery from Westborough, MA
Price includes $211 shipping
Great Deal

$26,476

$25,606

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 $2,152 shipping
Fair Deal

$39,376

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:
Radiant Red Tintcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
69,529
Stock #:
365965
VIN:
3GCUDFED9PG365965
Radiant Red Tintcoat 2023 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

69,529 mi

Home delivery from Euless, TX
Price includes $2,491 shipping
Good Deal

$39,363

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
Transmission:
Automatic
Mileage:
64,125
Stock #:
SS26252
VIN:
1GCPYFED5MZ209404
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

64,125 mi

Lake Katrine, NY
45 mi away
Good Deal
Manufacturer certified

$36,629

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:
21,809
Stock #:
9D0339A
VIN:
3GCUDFED9RG253993
Summit White 2024 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,762

 

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

21,809 mi

Home delivery from Cleveland, OH
Price includes $871 shipping
Good Deal

$50,765

$49,003

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
Transmission:
Automatic
Mileage:
94,868
Stock #:
14868
VIN:
1GCPYFED7MZ185476
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

94,868 mi

Home delivery from Front Royal, VA
Price includes $532 shipping
Fair Deal

$33,521

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

Fort Montgomery, NY
14 mi away
Great Deal

$32,994

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Shadow Gray Metallic
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,381
Stock #:
NU0284A
VIN:
1GCPYFEDXNZ183030
Shadow Gray Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,381 mi

Newburgh, NY
15 mi away
Fair Deal

$39,875

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 $658 shipping
Good Deal

$47,048

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:
Black
Transmission:
Automatic
Mileage:
109,511
Stock #:
5061
VIN:
3GCPYFEL3MG145581
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

109,511 mi

Home delivery from Seekonk, MA
Price includes $351 shipping
Fair Deal

$31,845

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:
Gray (Steel Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
41,748
Stock #:
X218019
VIN:
3GCPYFED1MG288019
Gray (Steel Metallic) 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
New arrival

 

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

41,748 mi

Home delivery from Atlantic City, NJ
Free home delivery
Fair Deal

$39,794

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Shadow Gray Metallic
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
80,435
Stock #:
T219787A
VIN:
1GCUYFET4NZ219787
Shadow Gray Metallic 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic
Price drop

-$1,500

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

80,435 mi

Pawling, NY
37 mi away
Good Deal

$33,675

$32,175

Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,338
Stock #:
C216652
VIN:
1GCPYFEL3NZ216652
Gray 2022 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

23,338 mi

Home delivery from Weymouth, MA
Price includes $273 shipping
Good Deal

$44,260

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
Transmission:
Automatic
Mileage:
64,125
Stock #:
SS26252
VIN:
1GCPYFED5MZ209404
Black 2021 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

Sponsored Listing

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

64,125 mi

Lake Katrine, NY
45 mi away
Good Deal
Manufacturer certified

$36,629

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 $23,418.00 to $77,492.05 with an average price of $30,365.21. 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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