Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearNaples, FL
275 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Automatic
- Mileage:
- 320
- Stock #:
- TG129771
- VIN:
- 3GCUKFED0TG129771
Sponsored by Group 1 Chevrolet Estero Bay
2026 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
320 mi
Estero, FL
20 mi away
Good Deal
$56,840
- 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:
- 50,353
- Stock #:
- NMG281772
- VIN:
- 3GCPYFED9MG281772
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,353 mi
Palmetto Bay, FL
97 mi away
Good Deal
$33,899
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 131,025
- Stock #:
- Z356332A
- VIN:
- 1GCPYFED4MZ273031
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
131,025 mi
Miami, FL
98 mi away
Good Deal
$23,990
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 68,325
- Stock #:
- PG331309
- VIN:
- 3GCUDFEL4PG331309
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
68,325 mi
Estero, FL
20 mi away
Fair Deal
$40,550
- 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:
- 51,238
- Stock #:
- 161583
- VIN:
- 3GCUDFED1PG291568
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
51,238 mi
Margate, FL
99 mi away
Fair Deal
$39,299
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 116,788
- Stock #:
- LZ205401
- VIN:
- 1GCPYFEL4LZ205401
Price drop
-$1,180
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
116,788 mi
Fort Myers, FL
28 mi away
Great Deal
$27,089
$25,909
- 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 $1,336 shipping
Fair Deal
$37,981
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Mileage:
- 50,948
- Stock #:
- 184401
- VIN:
- 1GCPYFEL3NZ184401
New arrival
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,948 mi
Home delivery from Orlando, FL
Price includes $177 shipping
Fair Deal
$39,164
- 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 Naples, FL
Price includes $999 shipping
Fair Deal
$40,997
- 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:
- 49,833
- Stock #:
- Z601536B
- VIN:
- 3GCPYFEL5MG148224
Price drop
-$3,498
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
49,833 mi
Homestead, FL
95 mi away
Great Deal
$35,991
$33,991
- 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 White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 57,426
- Stock #:
- 5307A
- VIN:
- 3GCUDFET7NG622691
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,426 mi
Home delivery from Seffner, FL
Price includes $147 shipping
Great Deal
$36,126
- 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
Price drop
-$6,191
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
26,139 mi
Home delivery from Brunswick, GA
Price includes $300 shipping
Good Deal
$51,792
$45,601
- 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
$17,817
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 28,198
- Stock #:
- NG682676
- VIN:
- 3GCUDFED2NG682676
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
28,198 mi
Estero, FL
20 mi away
Good Deal
$40,940
- 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:
- 92,485
- Stock #:
- T6605A
- VIN:
- 1GCPYFED6MZ453563
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
92,485 mi
Home delivery from Tampa, FL
Price includes $206 shipping
Good Deal
$29,186
- 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:
- White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 79,354
- Stock #:
- 3302504A
- VIN:
- 3GCPYFED5LG302504
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
79,354 mi
Labelle, FL
47 mi away
Good Deal
$31,052
- Year:
- 2026
- 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:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 8,188
- Stock #:
- E36854A
- VIN:
- 3GCUKFE86TG116879
2026 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
8,188 mi
Home delivery from Orlando, FL
Price includes $531 shipping
Good Deal
$51,825
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,785
- Stock #:
- 4158566B
- VIN:
- 1GCPYFED1MZ252363
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
54,785 mi
Miami, FL
95 mi away
Great Deal
$31,990
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 74,812
- Stock #:
- 1200040A
- VIN:
- 1GCPYFEDXKZ427514
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
74,812 mi
Miami, FL
98 mi away
Great Deal
$24,990
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,804
- Stock #:
- 1230519A
- VIN:
- 3GCPYFED7MG137055
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,804 mi
Miami, FL
95 mi away
Great Deal
$31,990
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 114,561
- Stock #:
- 196611
- VIN:
- 1GCPYFED9MZ196611
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
114,561 mi
Home delivery from Buford, GA
Price includes $576 shipping
Fair Deal
$29,524
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 75,630
- Stock #:
- TZ378219A
- VIN:
- 3GCPDFEK4PG190701
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
75,630 mi
Home delivery from Delray Beach, FL
Price includes $327 shipping
Good Deal
$34,146
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,282
- Stock #:
- G313726A
- VIN:
- 3GCUDFED0PG244497
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
59,282 mi
Miami, FL
98 mi away
Great Deal
$35,990
- 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:
- 50,587
- Stock #:
- G409254A
- VIN:
- 3GCUDFE86PG214701
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,587 mi
Miami, FL
98 mi away
Fair Deal
$40,990
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 $21,148.50 to $77,471.70 with an average price of $28,521.94. 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 $25,962.55. The average price has decreased by -5.2% since last year. The 251 for sale near Naples, FL on CarGurus, range from $21,148 to $77,472 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Naples, FL have no reported accidents or damage?
238 out of 251 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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