Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearMadison, WI
400 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
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Summit Wht
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Gideon/Very Dark Atmosphere Hv5
- Transmission:
- Automatic
- Mileage:
- 75,330
- Stock #:
- 266851
- VIN:
- 3GCUDFETXNG574460
Sponsored by Symdon Chevrolet
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
75,330 mi
Evansville, WI
21 mi away
Fair Deal
$39,180
- 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:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 83,358
- Stock #:
- PZ383841
- VIN:
- 1GCPYFED1KZ383841
Sponsored Listing
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
83,358 mi
Savanna, IL
77 mi away
Good Deal
$30,830
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 52,428
- Stock #:
- P3532
- VIN:
- 3GCUDFED6NG581849
Sponsored Listing
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
52,428 mi
Woodstock, IL
72 mi away
Good Deal
$40,877
- 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:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 99,364
- Stock #:
- H826026
- VIN:
- 1GCPYFED8KZ307095
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
99,364 mi
Home delivery from Green Bay, WI
Price includes $123 shipping
Fair Deal
$30,093
- 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:
- 95,906
- Stock #:
- P17617A
- VIN:
- 1GCPYFED3KZ381671
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
95,906 mi
Mukwonago, WI
57 mi away
Fair Deal
$30,222
- 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
- Transmission:
- Automatic
- Mileage:
- 46,367
- Stock #:
- 19509A
- VIN:
- 3GCUDFED3RG333838
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
46,367 mi
Lancaster, WI
68 mi away
Good Deal
$45,172
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 113,010
- Stock #:
- KB3333A
- VIN:
- 3GCUYFET7NG206578
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
113,010 mi
Kenosha, WI
81 mi away
Fair Deal
$33,249
- 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:
- 65,777
- Stock #:
- P1847
- VIN:
- 3GCUDFED5RG159187
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
65,777 mi
Schaumburg, IL
98 mi away
Good Deal
$42,313
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 31,517
- Stock #:
- 24805A
- VIN:
- 3GCPYFED5MG422773
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
31,517 mi
Saukville, WI
77 mi away
Good Deal
$38,398
- 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:
- 85,446
- Stock #:
- E50320
- VIN:
- 1GCPYFED3NZ156820
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
85,446 mi
Coloma, WI
68 mi away
Fair Deal
$34,308
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 28,477
- Stock #:
- 22X769
- VIN:
- 3GCPDFEK9RG286181
Price drop
-$1,819
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
28,477 mi
Platteville, WI
57 mi away
Great Deal
$42,812
$40,993
- 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:
- 37,270
- Stock #:
- 42478A
- VIN:
- 1GCPYFED5MZ342390
Price drop
-$1,212
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
37,270 mi
Baraboo, WI
36 mi away
Good Deal
$39,615
$38,802
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 93,719
- Stock #:
- PCF1358
- VIN:
- 3GCPYFED4LG308875
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,719 mi
Elgin, IL
93 mi away
Fair Deal
$30,083
- 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:
- 131,425
- Stock #:
- R5526A
- VIN:
- 3GCPYFED8KG189114
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
131,425 mi
Rochelle, IL
81 mi away
Good Deal
$25,172
- 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:
- Ash
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 28,579
- Stock #:
- K8763
- VIN:
- 3GCUDFEDXRG145527
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
28,579 mi
East Dundee, IL
89 mi away
Fair Deal
$48,263
- 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:
- Riptide Blue Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 7,799
- Stock #:
- 12F2191A
- VIN:
- 3GCUKFED8SG264561
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
7,799 mi
Hortonville, WI
96 mi away
Good Deal
$51,399
- 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:
- 47,877
- Stock #:
- 53757
- VIN:
- 1GCPYFED6NZ106347
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
47,877 mi
Home delivery from Cambridge, OH
Price includes $340 shipping
Great Deal
$36,918
- 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:
- 100,770
- Stock #:
- C20632PC
- VIN:
- 1GCPYFED0MZ197596
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
100,770 mi
Milwaukee, WI
74 mi away
Good Deal
$30,986
- 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:
- 39,609
- Stock #:
- MK260615A
- VIN:
- 3GCPYFED6MG479144
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
39,609 mi
McHenry, IL
77 mi away
Fair Deal
$38,410
- 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:
- Lakeshore Blue Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 28,073
- Stock #:
- 51367
- VIN:
- 3GCPDFEK1RG205836
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
28,073 mi
Middleton, WI
7 mi away
Good Deal
$43,889
- 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:
- 109,126
- Stock #:
- N260273A
- VIN:
- 1GCPYFED9NZ156241
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
109,126 mi
Home delivery from Downers Grove, IL
Price includes $224 shipping
Great Deal
$26,400
- 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:
- Red
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 92,102
- Stock #:
- K8819
- VIN:
- 1GCPYFED9KZ101154
New arrival
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
92,102 mi
East Dundee, IL
89 mi away
Fair Deal
$30,263
- 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:
- Silver
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 79,704
- Stock #:
- 420298
- VIN:
- 1GCPYFED2MZ420298
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
79,704 mi
Home delivery from Pelham, AL
Price includes $1,034 shipping
Fair Deal
$35,312
- 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:
- 39,609
- Stock #:
- MK260615A
- VIN:
- 3GCPYFED6MG479144
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
39,609 mi
McHenry, IL
77 mi away
Fair Deal
$38,410
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 $21,467.00 to $74,550.40 with an average price of $29,541.81. 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 Madison, WI?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,618.01. The average price has decreased by -1.5% since last year. The 309 for sale near Madison, WI on CarGurus, range from $21,467 to $74,550 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Madison, WI have no reported accidents or damage?
297 out of 309 for sale near Madison, 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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