Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearWindsor, MA
376 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:
- 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:
- 42,250
- Stock #:
- C91134L
- VIN:
- 3GCPKFEK0SG208271
New arrival
Sponsored by Merchants Automotive Group
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
42,250 mi
Hooksett, NH
90 mi away
Fair Deal
$43,772
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 56,823
- Stock #:
- M5065MV
- VIN:
- 3GCPDFEK0NG605137
Sponsored Listing
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
56,823 mi
Rhinebeck, NY
58 mi away
Fair Deal
$36,075
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 40,052
- Stock #:
- P17867A
- VIN:
- 3GCUDFEL8RG130662
Sponsored Listing
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
40,052 mi
Palmer, MA
44 mi away
Good Deal
$48,771
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 104,003
- Stock #:
- 114657
- VIN:
- 3GCPYFED6KG295660
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
104,003 mi
Auburn, MA
64 mi away
Great Deal
$25,294
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 60,261
- Stock #:
- 25T395A
- VIN:
- 1GCPYFED8MZ137470
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
60,261 mi
Townsend, MA
69 mi away
Good Deal
$34,144
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Ash
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 42,557
- Stock #:
- 8T2250
- VIN:
- 3GCPDFEK2NG534068
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
42,557 mi
Albany, NY
39 mi away
Good Deal
$34,950
- 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:
- 57,228
- Stock #:
- R2184A
- VIN:
- 3GCPYFED3MG353498
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,228 mi
Old Saybrook, CT
90 mi away
Good Deal
$35,591
- 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:
- Red
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 114,937
- Stock #:
- 16059
- VIN:
- 1GCPYFED9MZ387025
New arrival
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
114,937 mi
Home delivery from Smithfield, NC
Price includes $1,124 shipping
Fair Deal
$30,623
- 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
Price drop
-$648
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
52,986 mi
Tilton, NH
99 mi away
Great Deal
$33,062
$32,414
- 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:
- 111,897
- Stock #:
- 26523A
- VIN:
- 1GCPYFED4MZ259257
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
111,897 mi
Londonderry, NH
90 mi away
Good Deal
$27,594
- 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
-$1,200
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
69,513 mi
Nashua, NH
79 mi away
Great Deal
$31,995
$30,795
- 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 $1,185 shipping
Great Deal
$37,164
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- White (Iridescent Pearl Tricoat)
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 46,794
- Stock #:
- NZ166866
- VIN:
- 1GCPYFED0NZ166866
Price drop
-$2,008
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
46,794 mi
Manchester, NH
87 mi away
Great Deal
$36,590
$34,582
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 83,632
- Stock #:
- 49132A
- VIN:
- 3GCUDFEL1NG545204
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
83,632 mi
Mendon, MA
83 mi away
Fair Deal
$38,467
- 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:
- Automatic
- Mileage:
- 57,792
- Stock #:
- 195481T
- VIN:
- 1GCPYFED6MZ195481
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,792 mi
Home delivery from Gorham, NH
Price includes $310 shipping
Great Deal
$33,659
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 74,174
- Stock #:
- AC9469
- VIN:
- 3GCPYFEL3MG146472
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
74,174 mi
Old Saybrook, CT
90 mi away
Fair Deal
$35,373
- 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:
- 100,641
- Stock #:
- 9490B
- VIN:
- 1GCPYFED0MZ324203
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
100,641 mi
Ludlow, VT
63 mi away
Good Deal
$28,295
- 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
Albany, NY
39 mi away
Good Deal
$42,125
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,254
- Stock #:
- P19332A
- VIN:
- 3GCPDFEK8NG510132
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
50,254 mi
Mendon, MA
81 mi away
Good Deal
$35,467
- 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:
- Red
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 67,817
- Stock #:
- U0900322
- VIN:
- 1GCPYFEL8MZ221327
Price drop
-$1,457
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,817 mi
Tilton, NH
99 mi away
Good Deal
$35,442
$33,985
- 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:
- 61,183
- Stock #:
- 10T3308
- VIN:
- 3GCPYFED8MG360897
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
61,183 mi
Albany, NY
39 mi away
Good Deal
$34,625
- 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:
- 35,067
- Stock #:
- T20912
- VIN:
- 3GCPDFEK8PG120912
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
35,067 mi
Concord, NH
91 mi away
Good Deal
$40,683
- 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:
- 46,801
- Stock #:
- CTG414945A
- VIN:
- 3GCUDFED0NG690369
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
46,801 mi
Framingham, MA
85 mi away
Good Deal
$39,999
- 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:
- 61,183
- Stock #:
- 10T3308
- VIN:
- 3GCPYFED8MG360897
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
61,183 mi
Albany, NY
39 mi away
Good Deal
$34,625
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 $23,602.00 to $78,037.80 with an average price of $28,518.43. 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 Windsor, MA?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $25,993.05. The average price has decreased by -5.1% since last year. The 285 for sale near Windsor, MA on CarGurus, range from $23,602 to $78,038 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Windsor, MA have no reported accidents or damage?
275 out of 285 for sale near Windsor, MA 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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