Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearNaples, FL
301 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,138
- Stock #:
- G257521A
- VIN:
- 3GCUKFED0SG119921
Sponsored by Bomnin Chevrolet West Kendall
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
14,138 mi
Miami, FL
95 mi away
Fair Deal
$50,489
- 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:
- 36,281
- Stock #:
- G414665A
- VIN:
- 3GCUDFED1RG290651
Sponsored Listing
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
36,281 mi
Miami, FL
98 mi away
Good Deal
$43,989
- 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:
- 89,585
- Stock #:
- T260831423T1
- VIN:
- 1GCPYFED4KZ405749
New arrival
Sponsored Listing
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
89,585 mi
Davie, FL
96 mi away
Good Deal
$26,937
- 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:
- 16,365
- Stock #:
- 277974T
- VIN:
- 3GCPKFEK5SG277974
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
16,365 mi
Home delivery from Orlando, FL
Price includes $500 shipping
Great Deal
$45,303
- Year:
- 2026
- 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:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 650
- Stock #:
- G288232A
- VIN:
- 3GCUKFE80TG250271
2026 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
650 mi
Home delivery from Jacksonville, FL
Price includes $294 shipping
Great Deal
$54,357
- 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 $147 shipping
Great Deal
$30,139
- 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
-$1,095
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
$31,489
$30,394
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 81,059
- Stock #:
- 5118748
- VIN:
- 1GCPYFED2KZ118748
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
81,059 mi
Belle Glade, FL
80 mi away
Good Deal
$29,052
- Year:
- 2026
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 531
- Stock #:
- R87995
- VIN:
- 3GCUKFED4TG108731
2026 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
531 mi
Home delivery from Herculaneum, MO
Price includes $1,966 shipping
Fair Deal
$56,987
- 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
Port Charlotte, FL
64 mi away
Fair Deal
$35,260
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 156,989
- Stock #:
- 104856
- VIN:
- 1GCPYFED1KZ104856
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
156,989 mi
Hollywood, FL
99 mi away
Great Deal
$18,817
- 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:
- 83,889
- Stock #:
- T381751A
- VIN:
- 3GCUDFED7PG197131
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
83,889 mi
Punta Gorda, FL
56 mi away
Fair Deal
$37,829
- 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
Margate, FL
99 mi away
Fair Deal
$40,699
- 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:
- 111,384
- Stock #:
- TLB21786B
- VIN:
- 1GCPYFED4MZ250994
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
111,384 mi
Homestead, FL
95 mi away
Fair Deal
$27,985
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 114,952
- Stock #:
- SF183875
- VIN:
- 1GCPYFED2LZ183875
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
114,952 mi
Hollywood, FL
99 mi away
Fair Deal
$29,005
- 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:
- Lakeshore Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 28,692
- Stock #:
- T26384A
- VIN:
- 3GCUDFED2RG192440
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
28,692 mi
Home delivery from Hicksville, OH
Price includes $1,336 shipping
Good Deal
$45,726
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 41,084
- Stock #:
- TG381321A
- VIN:
- 3GCUDFED0RG209249
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
41,084 mi
Fort Lauderdale, FL
90 mi away
Good Deal
$43,785
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 26,139
- Stock #:
- RG341947
- VIN:
- 3GCUDFED4RG341947
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
26,139 mi
Home delivery from Brunswick, GA
Price includes $300 shipping
Fair Deal
$49,750
- 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 $1,750 shipping
Fair Deal
$49,450
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,709
- Stock #:
- RG147096
- VIN:
- 3GCUDFEL9RG147096
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
53,709 mi
Estero, FL
20 mi away
Good Deal
$45,550
- 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 $2,260 shipping
Fair Deal
$30,632
- 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:
- 87,776
- Stock #:
- 161562
- VIN:
- 1GCPYFED6LZ353199
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
87,776 mi
Miami, FL
99 mi away
Fair Deal
$30,999
- 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:
- 73,195
- Stock #:
- RG108360
- VIN:
- 3GCUDFED2RG108360
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
73,195 mi
Fort Myers, FL
27 mi away
Good Deal
$41,449
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 103,911
- Stock #:
- G418842A
- VIN:
- 3GCUDFEDXNG674860
Sponsored Listing
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
103,911 mi
Miami, FL
98 mi away
Fair Deal
$32,989
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 $20,352.50 to $75,455.05 with an average price of $29,258.59. 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 Naples, FL?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,594.65. The average price has decreased by -1.6% since last year. The 282 for sale near Naples, FL on CarGurus, range from $20,352 to $75,455 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Naples, FL have no reported accidents or damage?
272 out of 282 for sale near Naples, 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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