Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearEndeavor, WI
350 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- White
- Transmission:
- Automatic
- Mileage:
- 57,132
- Stock #:
- 612456
- VIN:
- 1GCPYFED8NZ162385
Price drop
-$1,000
Sponsored by S & L Motors
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,132 mi
Pulaski, WI
90 mi away
Good Deal
$37,494
$36,494
- Year:
- 2024
- 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:
- Jet Black, Leather-appointed front outboard seatin
- Transmission:
- Automatic
- Mileage:
- 34,856
- Stock #:
- 42753A
- VIN:
- 3GCUDFEL5RG286609
New arrival
Sponsored Listing
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
34,856 mi
Baraboo, WI
19 mi away
Fair Deal
$51,254
- 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:
- 98,127
- Stock #:
- KI6720A
- VIN:
- 3GCPYFED8MG267619
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
98,127 mi
Janesville, WI
71 mi away
Fair Deal
$31,407
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK, CLOTH SEAT TRIM
- Transmission:
- Automatic
- Mileage:
- 37,271
- Stock #:
- 42478A
- VIN:
- 1GCPYFED5MZ342390
Photos coming soon
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
37,271 mi
Baraboo, WI
19 mi away
Good Deal
$37,397
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 25,654
- Stock #:
- C15413A
- VIN:
- 3GCUDFED9RG454907
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
25,654 mi
Milwaukee, WI
86 mi away
Fair Deal
$48,414
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,902
- Stock #:
- P2588
- VIN:
- 3GCPKFEK4SG284530
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
38,902 mi
Beloit, WI
84 mi away
Great Deal
$41,299
- 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:
- SHADOW GRAY METALLIC
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 76,016
- Stock #:
- 2610058A
- VIN:
- 1GCPYFED9LZ218475
New arrival
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
76,016 mi
Green Bay, WI
91 mi away
Good Deal
$32,844
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 82,945
- Stock #:
- 5180
- VIN:
- 3GCPYFED6MG421423
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
82,945 mi
Home delivery from Seffner, FL
Price includes $1,213 shipping
Great Deal
$30,205
- 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:
- 8-Speed Automatic
- Mileage:
- 93,874
- Stock #:
- T1480B
- VIN:
- 3GCPYFED4KG212520
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,874 mi
Green Bay, WI
93 mi away
Fair Deal
$31,189
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- RADIANT RED TINTCOAT
- Interior color:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 35,518
- Stock #:
- 269901A
- VIN:
- 3GCUDFE81RG158265
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
35,518 mi
Appleton, WI
65 mi away
Fair Deal
$47,025
- 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:
- 8-Speed Automatic
- Mileage:
- 95,933
- Stock #:
- P17617A
- VIN:
- 1GCPYFED3KZ381671
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
95,933 mi
Mukwonago, WI
82 mi away
Fair Deal
$28,989
- 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:
- 91,317
- Stock #:
- 612449
- VIN:
- 1GCPYFED6LZ355423
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
91,317 mi
Pulaski, WI
90 mi away
Fair Deal
$30,995
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,607
- Stock #:
- T53541A
- VIN:
- 1GCPYFED5KZ417215
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
61,607 mi
Milwaukee, WI
81 mi away
Fair Deal
$33,494
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- White
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 44,431
- Stock #:
- 2511
- VIN:
- 3GCUDFE81RG144348
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
44,431 mi
Milton, WI
69 mi away
Fair Deal
$46,488
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 80,500
- Stock #:
- 2600775A
- VIN:
- 1GCPYFED8MZ326748
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
80,500 mi
Home delivery from El Paso, IL
Price includes $399 shipping
Fair Deal
$34,774
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 44,023
- Stock #:
- C0750A
- VIN:
- 1GCPYFED6MZ401964
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
44,023 mi
Wausau, WI
85 mi away
Fair Deal
$38,446
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- White
- Transmission:
- Automatic
- Mileage:
- 57,132
- Stock #:
- 612456
- VIN:
- 1GCPYFED8NZ162385
Price drop
-$1,000
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,132 mi
Pulaski, WI
90 mi away
Good Deal
$37,494
$36,494
- 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:
- 6,046
- Stock #:
- 0966A
- VIN:
- 3GCUKFED4SG371154
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
6,046 mi
Home delivery from Waynesville, MO
Price includes $1,290 shipping
Good Deal
$51,775
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 117,208
- Stock #:
- LG369340
- VIN:
- 3GCPYFED6LG369340
Price drop
-$693
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
117,208 mi
Sparta, WI
69 mi away
Fair Deal
$28,856
$28,163
- 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:
- 57,586
- Stock #:
- 15042A1
- VIN:
- 3GCUDFED8PG245445
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,586 mi
Chilton, WI
70 mi away
Good Deal
$40,398
- Year:
- 2024
- 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:
- 37,160
- Stock #:
- P23285
- VIN:
- 3GCUDFEL1RG140403
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
37,160 mi
Madison, WI
45 mi away
Good Deal
$48,788
- 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:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 39,028
- Stock #:
- 442637A
- VIN:
- 1GCPYFED9MZ442637
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
39,028 mi
Home delivery from Sykesville, MD
Price includes $900 shipping
Good Deal
$37,694
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 65,598
- Stock #:
- PC26174A
- VIN:
- 3GCUDFET1NG512638
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
65,598 mi
Home delivery from Hicksville, OH
Price includes $366 shipping
Good Deal
$37,756
- 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:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 25,863
- Stock #:
- 261200A
- VIN:
- 1GCPYFED9MZ203959
New arrival
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
25,863 mi
Janesville, WI
73 mi away
Fair Deal
$42,376
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 $23,147.00 to $71,072.60 with an average price of $28,711.00. 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
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
FAQs
How much does the Chevrolet Silverado 1500 LT Trail Boss cost in Endeavor, WI?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,155.61. The average price has decreased by -4.2% since last year. The 269 for sale near Endeavor, WI on CarGurus, range from $23,147 to $71,073 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Endeavor, WI have no reported accidents or damage?
255 out of 269 for sale near Endeavor, WI have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 LT Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 LT Trail Boss gets between 15 and 24 MPG/MPGe.
What fuel types are available?
Diesel, Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
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