Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearWilton, CT
305 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,073
- Stock #:
- N5673K
- VIN:
- 3GCUDFELXRG262998
Sponsored by Blasius North
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
24,073 mi
Torrington, CT
46 mi away
Good Deal
$49,747
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 16,005
- Stock #:
- X382514
- VIN:
- 3GCUKFED8SG382514
Sponsored Listing
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
16,005 mi
Pawling, NY
23 mi away
Good Deal
$50,000
- 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:
- 67,817
- Stock #:
- PU6673V
- VIN:
- 1GCPYFED5MZ255590
Price drop
-$1,495
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,817 mi
Wappingers Falls, NY
35 mi away
Great Deal
$33,170
$31,675
- 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:
- 93,410
- Stock #:
- ELA49867A
- VIN:
- 1GCPYFED7MZ191021
Price drop
-$2,450
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,410 mi
Watertown, CT
31 mi away
Great Deal
$31,049
$28,599
- 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:
- 69,513
- Stock #:
- 110852
- VIN:
- 1GCPYFED4LZ148125
Price drop
-$1,000
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
69,513 mi
Home delivery from Nashua, NH
Price includes $441 shipping
Good Deal
$33,436
$32,436
- 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:
- 79,882
- Stock #:
- MZ216664
- VIN:
- 1GCPYFEL1MZ216664
Price drop
-$1,501
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
79,882 mi
Commack, NY
27 mi away
Great Deal
$31,625
$30,124
- 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:
- Automatic
- Mileage:
- 96,914
- Stock #:
- 29310
- VIN:
- 1GCPYFED5KZ129310
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
96,914 mi
West Islip, NY
34 mi away
Great Deal
$24,777
- 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:
- 52,986
- Stock #:
- N4600056AA
- VIN:
- 3GCPYFED0MG371604
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
52,986 mi
Home delivery from Tilton, NH
Price includes $362 shipping
Great Deal
$33,458
- 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:
- 43,301
- Stock #:
- C13464
- VIN:
- 3GCUDFED7RG271702
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
43,301 mi
Freeport, NY
39 mi away
Good Deal
$43,174
- 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:
- 67,817
- Stock #:
- PU6673V
- VIN:
- 1GCPYFED5MZ255590
Price drop
-$1,495
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,817 mi
Wappingers Falls, NY
35 mi away
Great Deal
$33,170
$31,675
- 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 $1,093 shipping
Great Deal
$30,085
- 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:
- Cajun Red Tintcoat
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 89,790
- Stock #:
- 1919105
- VIN:
- 3GCPYFED9KG119105
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
89,790 mi
Naugatuck, CT
28 mi away
Good Deal
$28,793
- 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:
- 47,362
- Stock #:
- 9T3218
- VIN:
- 1GCPYFED8MZ119969
Price drop
-$818
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
47,362 mi
Home delivery from Albany, NY
Price includes $180 shipping
Good Deal
$37,123
$36,305
- 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:
- 81,687
- Stock #:
- 169326-C
- VIN:
- 3GCPYFEL6NG169326
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
81,687 mi
Home delivery from Richardson, TX
Price includes $1,749 shipping
Fair Deal
$32,639
- 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:
- 51,526
- Stock #:
- U20698T
- VIN:
- 3GCUDFED4RG120428
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
51,526 mi
St James, NY
29 mi away
Fair Deal
$44,996
- 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
- Transmission:
- Automatic
- Mileage:
- 113,666
- Stock #:
- 38302
- VIN:
- 1GCPYFED0MZ434958
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
113,666 mi
Patchogue, NY
37 mi away
Good Deal
$26,170
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 35,347
- Stock #:
- TCT577A
- VIN:
- 3GCUDFEL5RG408742
Price drop
-$899
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
35,347 mi
Home delivery from Laconia, NH
Price includes $384 shipping
Great Deal
$45,183
$44,284
- 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 $400 shipping
Good Deal
$37,194
- 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:
- 84,826
- Stock #:
- TR12484A
- VIN:
- 3GCPYFEL9MG260704
Price drop
-$1,750
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
84,826 mi
Waterbury, CT
33 mi away
Great Deal
$32,746
$30,996
- 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 $732 shipping
Fair Deal
$38,122
- 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:
- 32,276
- Stock #:
- 7P1493
- VIN:
- 3GCUDFEDXPG150532
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
32,276 mi
Home delivery from Albany, NY
Price includes $180 shipping
Good Deal
$42,305
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 105,491
- Stock #:
- P17844
- VIN:
- 1GCPYFED9LZ176888
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
105,491 mi
Home delivery from Palmer, MA
Free home delivery
Fair Deal
$28,771
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 106,679
- Stock #:
- AV4924
- VIN:
- 3GCPYFED8LG223912
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
106,679 mi
Home delivery from Kirtland, OH
Price includes $412 shipping
Good Deal
$26,305
- 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:
- 51,526
- Stock #:
- U20698T
- VIN:
- 3GCUDFED4RG120428
Sponsored Listing
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
51,526 mi
St James, NY
29 mi away
Fair Deal
$44,996
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 $21,308.75 to $72,489.70 with an average price of $28,755.94. 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 Wilton, CT?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,192.85. The average price has decreased by -4% since last year. The 305 for sale near Wilton, CT on CarGurus, range from $21,309 to $72,490 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Wilton, CT have no reported accidents or damage?
281 out of 305 for sale near Wilton, CT 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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