Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearMadison, WI
414 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:
- 75,405
- Stock #:
- 266851
- VIN:
- 3GCUDFETXNG574460
Sponsored by Symdon Chevrolet
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
75,405 mi
Evansville, WI
21 mi away
Fair Deal
$36,891
- Year:
- 2023
- 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:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 42,438
- Stock #:
- 03P903
- VIN:
- 3GCUDFEL8PG357864
New arrival
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
42,438 mi
Mount Carroll, IL
74 mi away
Fair Deal
$45,683
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 6.2L V8
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 57,388
- Stock #:
- P30657
- VIN:
- 3GCPYFEL8MG248009
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,388 mi
Janesville, WI
31 mi away
Good Deal
$36,014
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,306
- Stock #:
- S1497A
- VIN:
- 1GCPYFEL9MZ362925
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
54,306 mi
Rochelle, IL
79 mi away
Good Deal
$36,093
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 79,504
- Stock #:
- 96000
- VIN:
- 3GCPYFED8KG263535
Price drop
-$1,198
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
79,504 mi
Brodhead, WI
31 mi away
Good Deal
$31,193
$29,995
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 145,299
- Stock #:
- 16848ZA
- VIN:
- 1GCPYFED2KZ335023
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
145,299 mi
Fond Du Lac, WI
67 mi away
Fair Deal
$23,486
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,493
- Stock #:
- 08P925
- VIN:
- 3GCPDFEK5RG329169
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
27,493 mi
Morrison, IL
90 mi away
Good Deal
$41,658
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 76,912
- Stock #:
- I6155
- VIN:
- 3GCUDFED8PG270507
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
76,912 mi
Appleton, WI
96 mi away
Fair Deal
$37,494
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 88,267
- Stock #:
- 72060
- VIN:
- 1GCPYFEL8MZ407112
Price drop
-$804
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
88,267 mi
Sun Prairie, WI
11 mi away
Good Deal
$32,517
$31,713
- 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:
- Sterling Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 19,353
- Stock #:
- 37847A
- VIN:
- 3GCUKFED3SG354927
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
19,353 mi
Orfordville, WI
30 mi away
Fair Deal
$51,285
- 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
43 mi away
Great Deal
$40,298
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 25,119
- Stock #:
- 96018
- VIN:
- 3GCUDFED9RG126466
Price drop
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
25,119 mi
Brodhead, WI
31 mi away
Good Deal
$49,175
$45,996
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 90,088
- Stock #:
- TE144341B
- VIN:
- 3GCPYFEL6MG475053
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
90,088 mi
Bristol, WI
81 mi away
Great Deal
$29,620
- 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:
- 83,890
- Stock #:
- R2014A
- VIN:
- 1GCPYFEL2NZ199682
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
83,890 mi
Portage, WI
35 mi away
Good Deal
$32,432
- 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
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 11,643
- Stock #:
- P10031
- VIN:
- 3GCUDFED5RG396245
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
11,643 mi
Fox Lake, IL
77 mi away
Good Deal
$46,786
- 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:
- White (Iridescent Pearl Tricoat)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 33,336
- Stock #:
- A115208BB
- VIN:
- 3GCUDFEL0NG596502
Price drop
-$1,432
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
33,336 mi
Plymouth, WI
87 mi away
Good Deal
$44,039
$43,106
- 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:
- 101,522
- Stock #:
- 50109A
- VIN:
- 1GCPYFED4MZ128443
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
101,522 mi
Fox Lake, IL
77 mi away
Fair Deal
$29,367
- 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
- Transmission:
- Automatic
- Mileage:
- 37,248
- Stock #:
- R7496
- VIN:
- 3GCUDFEL3RG140239
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
37,248 mi
Crystal Lake, IL
80 mi away
Fair Deal
$46,701
- Year:
- 2024
- 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:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 35,038
- Stock #:
- P14695
- VIN:
- 3GCUDFE80RG170682
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
35,038 mi
Fox Lake, IL
77 mi away
Fair Deal
$46,167
- 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 (Steel Metallic)
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 67,822
- Stock #:
- 48155A
- VIN:
- 3GCPYFED7LG311849
Price drop
-$714
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,822 mi
Antioch, IL
78 mi away
Good Deal
$32,073
$31,359
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 93,040
- Stock #:
- PS3913
- VIN:
- 3GCPYFEL1MG458578
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,040 mi
St. Charles, IL
98 mi away
Good Deal
$29,913
- 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:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,103
- Stock #:
- Y1104
- VIN:
- 3GCPDFEK9RG359226
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
33,103 mi
Sheboygan, WI
95 mi away
Fair Deal
$42,225
- 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
- Transmission:
- Automatic
- Mileage:
- 37,099
- Stock #:
- 26C983A
- VIN:
- 3GCUDFEL1RG350841
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
37,099 mi
Oconomowoc, WI
46 mi away
Good Deal
$46,840
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 106,953
- Stock #:
- W15283B
- VIN:
- 1GCPYFED3LZ249642
Sponsored Listing
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
106,953 mi
West Bend, WI
64 mi away
Fair Deal
$29,138
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 $16,695.00 to $75,348.55 with an average price of $28,067.92. 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 $25,665.67. The average price has decreased by -5.6% since last year. The 324 for sale near Madison, WI on CarGurus, range from $16,695 to $75,349 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Madison, WI have no reported accidents or damage?
296 out of 324 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.
Relevant articles
CarGurus Editorial Team
Best Truck Lease Deals in November 2026
Leasing a truck can be a great way to get into one of the latest models, with the best technology, at a more affordable monthly price. Here are the best deals we've found this month.
CarGurus Editorial Team
Best Car Deals in November 2026
In the market for a new or used car this year? Whether you’re looking to buy or lease, we’ve collated a list of the best car deals available this month.
CarGurus Editorial Team
Car Deals with 0% APR in November 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
Chevrolet Silverado 1500 LT in Madison WIChevrolet Silverado 1500 RST in Madison WIChevrolet Silverado 1500 LTZ in Madison WIChevrolet Silverado 1500 LT Trail Boss in Madison WIChevrolet Silverado 1500 LT1 in Madison WIChevrolet Silverado 1500 Custom in Madison WIChevrolet Silverado 1500 High Country in Madison WIChevrolet Silverado 1500 Custom Trail Boss in Madison WIChevrolet Silverado 1500 Work Truck in Madison WI
Chevrolet Silverado 1500 in Janesville WIChevrolet Silverado 1500 in Rockford ILChevrolet Silverado 1500 in Fond du Lac WIChevrolet Silverado 1500 in Dubuque IAChevrolet Silverado 1500 in Milwaukee WIChevrolet Silverado 1500 in Kenosha WIChevrolet Silverado 1500 in Clinton IAChevrolet Silverado 1500 in Palatine ILChevrolet Silverado 1500 in Appleton WI
Chevrolet Silverado 1500 in Madison WIOld Chevy Trucks for Sale in Madison WIClassic Muscle Cars for Sale in Madison WIChevrolet Trucks For Sale in Madison WICheap Muscle Cars for Sale in Madison WIWork Trucks for Sale in Madison WIReliable Cars For Sale in Madison WIAmerican Made Trucks For Sale in Madison WIBest Pickup Trucks For Sale in Madison WIBest Cars Under $5,000 For Sale in Madison WI
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in MadisonUsed SUVs / Crossovers for Sale with Low Mileage in MadisonUsed Hatchbacks for Sale with Low Mileage in MadisonUsed Convertibles for Sale with Low Mileage in MadisonUsed Vans for Sale with Low Mileage in MadisonUsed Minivans for Sale with Low Mileage in MadisonUsed Pickup Trucks for Sale with Low Mileage in MadisonUsed Coupes for Sale with Low Mileage in MadisonUsed Wagons for Sale with Low Mileage in Madison
