Used Chevrolet Silverado 1500 LT Trail Boss for Sale near Upperville, VA
328 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 93,312
- Stock #:
- WP0333
- VIN:
- 1GCPYFED8LZ147477
Sponsored by HoneyCar
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,312 mi
Winchester, VA
22 mi away
Great Deal
$29,198
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 67,245
- Stock #:
- 26C1710A
- VIN:
- 3GCUDFEL7NG542484
Sponsored Listing
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,245 mi
Martinsburg, WV
37 mi away
Fair Deal
$41,475
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 23,387
- Stock #:
- C414500A
- VIN:
- 3GCUDFED9PG313851
New arrival
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
23,387 mi
Rockville, MD
40 mi away
Fair Deal
$46,800
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Northsky Blue Metallic
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 47,877
- Stock #:
- 53757
- VIN:
- 1GCPYFED6NZ106347
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
47,877 mi
Home delivery from Cambridge, OH
Price includes $161 shipping
Great Deal
$36,138
- 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:
- Radiant Red Tintcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 20,698
- Stock #:
- HP9810
- VIN:
- 3GCPKFEK5SG182864
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
20,698 mi
Woodbridge, VA
38 mi away
Good Deal
$46,195
- 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:
- Brown
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 43,769
- Stock #:
- 85214A
- VIN:
- 3GCUDFED6PG140001
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
43,769 mi
Home delivery from Mentor, OH
Price includes $402 shipping
Fair Deal
$44,345
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 23,387
- Stock #:
- C414500A
- VIN:
- 3GCUDFED9PG313851
New arrival
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
23,387 mi
Rockville, MD
40 mi away
Fair Deal
$46,800
- 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:
- 43,569
- Stock #:
- W1251A
- VIN:
- 3GCUDFED9RG341412
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
43,569 mi
Home delivery from Washington, PA
Price includes $546 shipping
Fair Deal
$46,986
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 101,768
- Stock #:
- LZ352522
- VIN:
- 1GCPYFED4LZ352522
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
101,768 mi
Winchester, VA
22 mi away
Good Deal
$29,132
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 23,786
- Stock #:
- C13391B
- VIN:
- 3GCUDFED2RG434787
Price drop
-$1,506
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
23,786 mi
Culpeper, VA
34 mi away
Great Deal
$47,499
$45,993
- 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:
- 54,595
- Stock #:
- 14608P
- VIN:
- 1GCPYFEDXMZ307263
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
54,595 mi
Fredericksburg, VA
47 mi away
Fair Deal
$38,599
- 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:
- 93,312
- Stock #:
- WP0333
- VIN:
- 1GCPYFED8LZ147477
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,312 mi
Winchester, VA
22 mi away
Great Deal
$29,198
- 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:
- Automatic
- Mileage:
- 117,682
- Stock #:
- KTTTKG296789
- VIN:
- 3GCPYFED6KG296789
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
117,682 mi
Vienna, VA
34 mi away
Good Deal
$26,995
- 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:
- Silver
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 79,704
- Stock #:
- 420298
- VIN:
- 1GCPYFED2MZ420298
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
79,704 mi
Home delivery from Pelham, AL
Price includes $933 shipping
Fair Deal
$34,613
- 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:
- 14,304
- Stock #:
- P1004
- VIN:
- 3GCUDFED8RG445261
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
14,304 mi
Warrenton, VA
14 mi away
Fair Deal
$51,488
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 28,090
- Stock #:
- B13726A
- VIN:
- 3GCUDFED0PG189131
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
28,090 mi
Home delivery from Willoughby, OH
Price includes $1,068 shipping
Good Deal
$44,066
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 108,604
- Stock #:
- 3024368
- VIN:
- 3GCUDFEDXPG200510
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
108,604 mi
Home delivery from Raleigh, NC
Price includes $528 shipping
Fair Deal
$33,928
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,500
- Stock #:
- 193772
- VIN:
- 3GCPYFED0KG193772
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
49,500 mi
Woodbridge, VA
38 mi away
Great Deal
$32,390
- 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:
- 33,836
- Stock #:
- S9360
- VIN:
- 3GCPKFEK2SG208899
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
33,836 mi
Home delivery from Salisbury, NC
Price includes $260 shipping
Good Deal
$44,147
- 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:
- 69,678
- Stock #:
- 63636XP
- VIN:
- 3GCUDFED7PG197811
Price drop
-$1,500
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
69,678 mi
Home delivery from Wake Forest, NC
Price includes $297 shipping
Good Deal
$40,895
$39,395
- 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:
- 56,701
- Stock #:
- G6386A
- VIN:
- 3GCPYFED8KG147896
New arrival
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
56,701 mi
Home delivery from Titusville, PA
Price includes $324 shipping
Fair Deal
$34,714
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 68,827
- Stock #:
- 436128
- VIN:
- 1GCPYFEL3MZ436128
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
68,827 mi
Home delivery from Buford, GA
Price includes $469 shipping
Fair Deal
$36,768
- 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:
- 63,075
- Stock #:
- T266459LB
- VIN:
- 3GCPYFED9MG321932
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
63,075 mi
Home delivery from Rochester, NY
Price includes $456 shipping
Good Deal
$34,955
- 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:
- 41,768
- Stock #:
- 2X50261A
- VIN:
- 1GCPYFED0MZ446835
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
41,768 mi
Chantilly, VA
22 mi away
Fair Deal
$40,448
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 $21,482.50 to $75,045.70 with an average price of $29,059.98. 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 Upperville, VA?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,507.36. The average price has decreased by -2% since last year. The 328 for sale near Upperville, VA on CarGurus, range from $21,482 to $75,046 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Upperville, VA have no reported accidents or damage?
316 out of 328 for sale near Upperville, VA 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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