Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearCrestview, FL
343 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 87,368
- Stock #:
- 20677389A
- VIN:
- 3GCPYFED8KG239509
New arrival
Sponsored by Cannon Nissan Eastern Shore
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
87,368 mi
Daphne, AL
75 mi away
Fair Deal
$32,878
- 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:
- 12,248
- Stock #:
- SG224563
- VIN:
- 3GCUKFEDXSG224563
Sponsored Listing
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
12,248 mi
Mobile, AL
97 mi away
Fair Deal
$54,307
- 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:
- White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 130,411
- Stock #:
- TP4271
- VIN:
- 3GCUDFED4PG160537
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
130,411 mi
Troy, AL
80 mi away
Fair Deal
$35,306
- 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:
- White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 102,314
- Stock #:
- 10006
- VIN:
- 3GCUDFED6PG349173
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
102,314 mi
Home delivery from Monroe, LA
Price includes $341 shipping
Fair Deal
$36,731
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 49,498
- Stock #:
- 260668TA
- VIN:
- 3GCUDFED0RG261092
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
49,498 mi
Home delivery from Bessemer, AL
Price includes $267 shipping
Good Deal
$45,763
- 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 $266 shipping
Good Deal
$33,946
- 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:
- Cherry Red Tintcoat
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 79,950
- Stock #:
- G11708A
- VIN:
- 1GCPYFEL4MZ350469
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
79,950 mi
Home delivery from Hillsboro, OR
Price includes $2,748 shipping
Fair Deal
$38,192
- 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 Ice Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 47,668
- Stock #:
- 15330
- VIN:
- 3GCPYFED0MG442476
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
47,668 mi
Home delivery from National City, CA
Price includes $2,150 shipping
Fair Deal
$41,145
- 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 $920 shipping
Good Deal
$39,310
- 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 $337 shipping
Great Deal
$30,329
- 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:
- 78,140
- Stock #:
- NZ133369
- VIN:
- 1GCPYFED8NZ133369
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
78,140 mi
Home delivery from Ridgeland, MS
Free home delivery
Good Deal
$36,401
- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 79,475
- Stock #:
- C421025A
- VIN:
- 1GCPYFED9MZ292092
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
79,475 mi
Bay Minette, AL
70 mi away
Good Deal
$35,432
- 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 $296 shipping
Great Deal
$54,359
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,996
- Stock #:
- P2874
- VIN:
- 3GCUDFED5RG343982
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,996 mi
Home delivery from Tuscaloosa, AL
Price includes $602 shipping
Fair Deal
$46,601
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Mileage:
- 48,591
- Stock #:
- PC790
- VIN:
- 3GCUDFED3RG264228
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
48,591 mi
Enterprise, AL
57 mi away
Good Deal
$45,584
- 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:
- 40,648
- Stock #:
- 4UT11275
- VIN:
- 3GCUDFED7PG287590
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
40,648 mi
Home delivery from Hattiesburg, MS
Price includes $172 shipping
Great Deal
$43,555
- 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 $688 shipping
Great Deal
$40,482
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,743
- Stock #:
- 11U7012A
- VIN:
- 1GCPYFED0KZ167012
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
82,743 mi
Daphne, AL
79 mi away
Good Deal
$31,028
- 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:
- Cherry Red Tintcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 39,028
- Stock #:
- 442637A
- VIN:
- 1GCPYFED9MZ442637
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
39,028 mi
Home delivery from Sykesville, MD
Price includes $900 shipping
Good Deal
$39,294
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 139,900
- Stock #:
- TR26335A
- VIN:
- 1GCPYFED6MZ212036
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
139,900 mi
Home delivery from Bourbonnais, IL
Price includes $1,086 shipping
Good Deal
$28,252
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 43,218
- Stock #:
- UV21113
- VIN:
- 1GCPYFED1MZ374835
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
43,218 mi
Home delivery from Tupelo, MS
Price includes $542 shipping
Good Deal
$38,114
- 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 $1,122 shipping
Good Deal
$56,143
- 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:
- 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:
- Red Hot
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 81,706
- Stock #:
- 18P49602
- VIN:
- 3GCPYFED5LG449602
Sponsored Listing
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
81,706 mi
Mobile, AL
91 mi away
Fair Deal
$34,577
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 $22,403.75 to $74,746.50 with an average price of $29,214.87. 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 Crestview, FL?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,593.15. The average price has decreased by -1.6% since last year. The 321 for sale near Crestview, FL on CarGurus, range from $22,404 to $74,746 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Crestview, FL have no reported accidents or damage?
311 out of 321 for sale near Crestview, 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.
Relevant articles
CarGurus Editorial Team
Best Cars for New Parents
Discover the best family cars for first-time parents in 2025, accounting for door access, car seat compatibility, and other real-world considerations new parents will want to keep in mind.
CarGurus Editorial Team
Best Truck Lease Deals in August 2026
Leasing a truck can be a great way to get into one of the latest models, with the best technology, at a more affordable monthly price. Here are the best deals we've found this month.
CarGurus Editorial Team
Car Deals with 0% APR in August 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
Chevrolet Silverado 1500 LT in Crestview FLChevrolet Silverado 1500 RST in Crestview FLChevrolet Silverado 1500 LTZ in Crestview FLChevrolet Silverado 1500 LT Trail Boss in Crestview FLChevrolet Silverado 1500 LT1 in Crestview FLChevrolet Silverado 1500 Custom in Crestview FLChevrolet Silverado 1500 High Country in Crestview FLChevrolet Silverado 1500 Custom Trail Boss in Crestview FLChevrolet Silverado 1500 Work Truck in Crestview FL
Chevrolet Silverado 1500 in Fort Walton Beach FLChevrolet Silverado 1500 in Pensacola FLChevrolet Silverado 1500 in Atmore ALChevrolet Silverado 1500 in Panama City FLChevrolet Silverado 1500 in Monroeville ALChevrolet Silverado 1500 in Dothan ALChevrolet Silverado 1500 in Marianna FLChevrolet Silverado 1500 in Mobile ALChevrolet Silverado 1500 in Montgomery AL
Chevrolet Silverado 1500 in Crestview FLOld Chevy Trucks for Sale in Crestview FLClassic Muscle Cars for Sale in Crestview FLChevrolet Trucks For Sale in Crestview FLCheap Muscle Cars for Sale in Crestview FLWork Trucks for Sale in Crestview FLReliable Cars For Sale in Crestview FLAmerican Made Trucks For Sale in Crestview FLBest Pickup Trucks For Sale in Crestview FLBest Cars Under $5,000 For Sale in Crestview FL
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in CrestviewUsed SUVs / Crossovers for Sale with Low Mileage in CrestviewUsed Hatchbacks for Sale with Low Mileage in CrestviewUsed Convertibles for Sale with Low Mileage in CrestviewUsed Vans for Sale with Low Mileage in CrestviewUsed Minivans for Sale with Low Mileage in CrestviewUsed Pickup Trucks for Sale with Low Mileage in CrestviewUsed Coupes for Sale with Low Mileage in CrestviewUsed Wagons for Sale with Low Mileage in Crestview
