Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearWinterset, IA
314 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:
- Black
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 75,291
- Stock #:
- 52193A
- VIN:
- 3GCPYFEL7NG173501
Sponsored by Shottenkirk Chevrolet Waukee
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
75,291 mi
Waukee, IA
21 mi away
Fair Deal
$35,466
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 65,540
- Stock #:
- A26287
- VIN:
- 3GCUDFED6RG263736
Sponsored Listing
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
65,540 mi
Iowa Falls, IA
90 mi away
Fair Deal
$43,700
- Year:
- 2025
- 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:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 21,293
- Stock #:
- 32791A
- VIN:
- 3GCUKFEL0SG273715
New arrival
Sponsored Listing
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
21,293 mi
Lake City, IA
74 mi away
Fair Deal
$55,680
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 67,685
- Stock #:
- 70177068
- VIN:
- 3GCUDFED9RG261494
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,685 mi
Store transfer to Urbandale, IA
Price includes $199 shipping
Good Deal
$40,197
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Northsky Blue Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,530
- Stock #:
- L248530
- VIN:
- 3GCUDFE8XPG248530
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
33,530 mi
Home delivery from Louisville, NE
Price includes $166 shipping
Good Deal
$43,760
- 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:
- 25,611
- Stock #:
- RG398281
- VIN:
- 3GCUDFED8RG398281
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
25,611 mi
Bellevue, NE
98 mi away
Great Deal
$45,939
- 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 $1,192 shipping
Great Deal
$30,684
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 109,414
- Stock #:
- 378696T
- VIN:
- 3GCPYFEL1MG378696
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
109,414 mi
Shenandoah, IA
81 mi away
Good Deal
$29,995
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 65,431
- Stock #:
- RG146763
- VIN:
- 3GCUDFEL6RG146763
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
65,431 mi
Bellevue, NE
98 mi away
Great Deal
$42,609
- Year:
- 2020
- 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:
- 127,448
- Stock #:
- CF26240A
- VIN:
- 1GCPYFEL7LZ319974
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
127,448 mi
Home delivery from Sullivan, MO
Price includes $536 shipping
Good Deal
$27,911
- 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:
- 106,679
- Stock #:
- AV4924
- VIN:
- 3GCPYFED8LG223912
New arrival
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
106,679 mi
Home delivery from Kirtland, OH
Price includes $656 shipping
Great Deal
$26,549
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 155,859
- Stock #:
- CS106437
- VIN:
- 1GCPYFED2KZ106437
New arrival
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
155,859 mi
Home delivery from Richardson, TX
Price includes $745 shipping
Fair Deal
$22,469
- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 86,250
- Stock #:
- 10991A
- VIN:
- 3GCPYFEL9MG466136
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
86,250 mi
Glidden, IA
61 mi away
Good Deal
$34,175
- Year:
- 2020
- 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:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 117,819
- Stock #:
- D8940B
- VIN:
- 3GCPYFEL4LG354634
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
117,819 mi
Waukee, IA
22 mi away
Great Deal
$27,077
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,846
- Stock #:
- 156238B
- VIN:
- 1GCPYFED4KZ156238
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
78,846 mi
Home delivery from Dallas, TX
Price includes $610 shipping
Good Deal
$31,335
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 88,940
- Stock #:
- 26190A
- VIN:
- 1GCPYFED5MZ291716
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
88,940 mi
Creston, IA
26 mi away
Good Deal
$32,575
- 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 $605 shipping
Good Deal
$38,230
- Year:
- 2022
- 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:
- 118,457
- Stock #:
- 196478
- VIN:
- 1GCPYFELXNZ196478
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
118,457 mi
Ottumwa, IA
86 mi away
Good Deal
$28,879
- 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:
- 8,097
- Stock #:
- P7331
- VIN:
- 3GCUDFELXRG354838
Price drop
-$2,385
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
8,097 mi
Home delivery from Saint Peters, MO
Price includes $316 shipping
Good Deal
$53,617
$51,232
- 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:
- White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,128
- Stock #:
- 28981596
- VIN:
- 3GCUKFED7SG285725
New arrival
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
53,128 mi
Store transfer to Urbandale, IA
Price includes $449 shipping
Good Deal
$43,447
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 80,751
- Stock #:
- 56312A
- VIN:
- 3GCPYFEL6MG258571
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
80,751 mi
Home delivery from Faribault, MN
Price includes $209 shipping
Great Deal
$33,156
- 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 $780 shipping
Good Deal
$51,265
- 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, Leather-Appointed Front Seat Trim
- Transmission:
- Automatic
- Mileage:
- 75,901
- Stock #:
- G261261A
- VIN:
- 1GCPYFEL4MZ374741
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
75,901 mi
Home delivery from Sullivan, MO
Price includes $536 shipping
Fair Deal
$36,531
- 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:
- 29,253
- Stock #:
- C2094A
- VIN:
- 3GCPYFED1LG313371
Sponsored Listing
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
29,253 mi
Knoxville, IA
49 mi away
Fair Deal
$40,208
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 $22,469.00 to $71,058.30 with an average price of $28,981.01. 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 Winterset, IA?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,270.08. The average price has decreased by -3.6% since last year. The 298 for sale near Winterset, IA on CarGurus, range from $22,469 to $71,058 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Winterset, IA have no reported accidents or damage?
277 out of 298 for sale near Winterset, IA 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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