Used Chevrolet Silverado 1500 LT Trail Boss for Sale near Webster, FL
289 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 58,352
- Stock #:
- 26558A
- VIN:
- 1GCPYFED4MZ396330
New arrival
Sponsored by Register Chevrolet
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
58,352 mi
Brooksville, FL
30 mi away
Fair Deal
$38,090
- 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:
- 66,431
- Stock #:
- 269842
- VIN:
- 1GCPYFEDXMZ269842
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
66,431 mi
Orlando, FL
39 mi away
Good Deal
$35,488
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 230,887
- Stock #:
- 26132
- VIN:
- 1GCPYFEL0LZ370300
Price drop
-$500
Sponsored Listing
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
230,887 mi
Ocala, FL
38 mi away
Great Deal
$19,399
$18,899
- 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
Seffner, FL
47 mi away
Great Deal
$30,492
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Slate Gray Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 39,923
- Stock #:
- CP1528
- VIN:
- 3GCUDFE89RG381928
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
39,923 mi
Dade City, FL
25 mi away
Fair Deal
$49,440
- 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:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 66,595
- Stock #:
- U23849
- VIN:
- 3GCUDFET8NG544955
Price drop
-$1,000
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
66,595 mi
Home delivery from Fort Myers, FL
Price includes $298 shipping
Good Deal
$36,798
$35,798
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 80,288
- Stock #:
- 324281
- VIN:
- 3GCPYFEL1LG324281
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
80,288 mi
Orlando, FL
37 mi away
Fair Deal
$37,388
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 26,597
- Stock #:
- I603170
- VIN:
- 3GCPDFEKXNG603170
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
26,597 mi
Ocala, FL
38 mi away
Good Deal
$39,598
- Year:
- 2023
- 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:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,702
- Stock #:
- 26X555A
- VIN:
- 3GCUDFE88PG262796
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
51,702 mi
Home delivery from Hickory, NC
Price includes $732 shipping
Great Deal
$40,626
- 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:
- 6,490
- Stock #:
- FV117643
- VIN:
- 1GCPYFEDXNZ117643
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
6,490 mi
Home delivery from Pompano Beach, FL
Free home delivery
Great Deal
$39,403
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Summit White
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 132,224
- Stock #:
- T171347
- VIN:
- 3GCUDFE82RG171347
Price drop
-$6,456
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
132,224 mi
Home delivery from West Palm Beach, FL
Free home delivery
Great Deal
$37,945
$31,489
- Year:
- 2023
- 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:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 33,371
- Stock #:
- PG296805
- VIN:
- 3GCPDFEK9PG296805
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
33,371 mi
Home delivery from Hillsboro, TX
Price includes $1,396 shipping
Fair Deal
$42,322
- 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:
- 85,114
- Stock #:
- 160889
- VIN:
- 1GCPYFED6MZ160889
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
85,114 mi
Orlando, FL
39 mi away
Good Deal
$32,988
- 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:
- 81,818
- Stock #:
- P
- VIN:
- 1GCPYFELXMZ192056
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
81,818 mi
Home delivery from Port Charlotte, FL
Price includes $117 shipping
Good Deal
$35,377
- 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:
- 30,158
- Stock #:
- 3024867
- VIN:
- 3GCUDFE81RG214253
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
30,158 mi
Home delivery from Raleigh, NC
Price includes $1,322 shipping
Fair Deal
$49,022
- 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:
- 107,155
- Stock #:
- 109315
- VIN:
- 3GCPYFED1LG109315
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
107,155 mi
Home delivery from Dawsonville, GA
Price includes $521 shipping
Fair Deal
$30,002
- 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:
- 100,891
- Stock #:
- 354690
- VIN:
- 1GCPYFEL3LZ354690
New arrival
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
100,891 mi
Home delivery from Crestwood, IL
Price includes $1,902 shipping
Fair Deal
$30,274
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 40,486
- Stock #:
- 23936
- VIN:
- 1GCPYFED9KZ268727
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
40,486 mi
Home delivery from Detroit, MI
Price includes $952 shipping
Good Deal
$33,261
- 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:
- 46,039
- Stock #:
- 45295836
- VIN:
- 3GCUDFED5RG295836
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
46,039 mi
Home delivery from Elba, AL
Free home delivery
Good Deal
$44,386
- 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:
- 58,352
- Stock #:
- 26558A
- VIN:
- 1GCPYFED4MZ396330
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
58,352 mi
Brooksville, FL
30 mi away
Fair Deal
$38,090
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,212
- Stock #:
- 161583
- VIN:
- 3GCUDFED1PG291568
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
51,212 mi
Home delivery from Margate, FL
Price includes $201 shipping
Fair Deal
$40,900
- 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:
- 74,820
- Stock #:
- T168300A
- VIN:
- 3GCPYFED4NG168300
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
74,820 mi
Home delivery from West Palm Beach, FL
Free home delivery
Good Deal
$35,094
- 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:
- 66,431
- Stock #:
- 269842
- VIN:
- 1GCPYFEDXMZ269842
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
66,431 mi
Orlando, FL
39 mi away
Good Deal
$35,488
- 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:
- 85,114
- Stock #:
- 160889
- VIN:
- 1GCPYFED6MZ160889
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
85,114 mi
Orlando, FL
39 mi away
Good Deal
$32,988
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 $18,899.00 to $82,630.00 with an average price of $29,524.23. 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 Webster, FL?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,643.47. The average price has decreased by -1.3% since last year. The 295 for sale near Webster, FL on CarGurus, range from $18,899 to $82,630 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Webster, FL have no reported accidents or damage?
287 out of 295 for sale near Webster, FL 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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