Used Chevrolet Silverado 1500 LT Trail Boss for Sale nearWindsor, ME
220 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Oxford Brown Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 72,157
- Stock #:
- 503
- VIN:
- 1GCPYFED6MZ298741
Sponsored by APlus Auto Group
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
72,157 mi
Windham, ME
54 mi away
Fair Deal
$37,299
- 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
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
57,792 mi
Gorham, NH
80 mi away
Fair Deal
$38,418
- 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
- Transmission:
- Automatic
- Mileage:
- 53,997
- Stock #:
- T709A
- VIN:
- 3GCPYFED5LG292668
Sponsored Listing
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
53,997 mi
Yarmouth, ME
45 mi away
Fair Deal
$36,484
- 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:
- 94,669
- Stock #:
- 214243T
- VIN:
- 1GCPYFEDXMZ214243
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
94,669 mi
Gorham, NH
80 mi away
Good Deal
$29,789
- 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:
- Blue
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,127
- Stock #:
- WYC-327096
- VIN:
- 3GCPYFED7MG327096
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
98,127 mi
Home delivery from Waukegan, IL
Price includes $927 shipping
Fair Deal
$34,103
- 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
- Transmission:
- Automatic
- Mileage:
- 53,997
- Stock #:
- T709A
- VIN:
- 3GCPYFED5LG292668
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
53,997 mi
Yarmouth, ME
45 mi away
Fair Deal
$36,484
- 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 $3,209 shipping
Fair Deal
$38,654
- 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:
- 8-Speed Automatic
- Mileage:
- 117,219
- Stock #:
- 1902
- VIN:
- 1GCPYFED2KZ362061
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
117,219 mi
Home delivery from West Bridgewater, MA
Price includes $175 shipping
Great Deal
$26,761
- 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 $615 shipping
Good Deal
$35,114
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 104,142
- Stock #:
- 70003191
- VIN:
- 3GCUDFEDXNG552080
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
104,142 mi
Store transfer to South Portland, ME
Price includes $1,599 shipping
Fair Deal
$35,597
- 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:
- 69,167
- Stock #:
- Z304754T
- VIN:
- 1GCPYFED7KZ304754
Price drop
-$1,575
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
69,167 mi
Home delivery from Defiance, OH
Price includes $1,554 shipping
Good Deal
$34,008
$32,433
- 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
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 127,360
- Stock #:
- 1lz144176
- VIN:
- 1GCPYFED1LZ144176
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
127,360 mi
Gardiner, ME
12 mi away
Good Deal
$25,901
- 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:
- 27,693
- Stock #:
- N26477A
- VIN:
- 3GCUDFED4RG128819
New arrival
2024 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
27,693 mi
Saco, ME
68 mi away
Fair Deal
$49,594
- 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:
- Red
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 141,310
- Stock #:
- 173849
- VIN:
- 1GCPYFED6LZ173849
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
141,310 mi
Home delivery from Ridgewood, NY
Price includes $416 shipping
Great Deal
$21,586
- 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:
- White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 91,729
- Stock #:
- T307B
- VIN:
- 1GCPYFED9MZ164368
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
91,729 mi
Yarmouth, ME
45 mi away
Good Deal
$30,984
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 1,780
- Stock #:
- 329247
- VIN:
- 3GCPKFEK3TG329247
New arrival
2026 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
1,780 mi
Home delivery from Cadiz, KY
Price includes $1,629 shipping
Fair Deal
$56,228
- 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
Gorham, NH
80 mi away
Fair Deal
$38,418
- 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:
- Blue
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 108,983
- Stock #:
- T626A
- VIN:
- 3GCPDFEK7NG557295
Price drop
-$1,499
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
108,983 mi
Yarmouth, ME
45 mi away
Good Deal
$31,484
$30,484
- 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 $992 shipping
Good Deal
$39,382
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 114,952
- Stock #:
- SF183875
- VIN:
- 1GCPYFED2LZ183875
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
114,952 mi
Home delivery from Hollywood, FL
Price includes $1,385 shipping
Great Deal
$29,199
- 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:
- 67,816
- Stock #:
- U0900322
- VIN:
- 1GCPYFEL8MZ221327
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,816 mi
Home delivery from Tilton, NH
Price includes $234 shipping
Good Deal
$38,156
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 26,838
- Stock #:
- T238A
- VIN:
- 3GCPDFEK6PG297524
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
26,838 mi
Wiscassett, ME
22 mi away
Great Deal
$40,949
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 68,884
- Stock #:
- KZ293208
- VIN:
- 1GCPYFED0KZ293208
New arrival
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
68,884 mi
Saco, ME
69 mi away
Fair Deal
$33,036
- 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:
- White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 91,729
- Stock #:
- T307B
- VIN:
- 1GCPYFED9MZ164368
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
91,729 mi
Yarmouth, ME
45 mi away
Good Deal
$30,984
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 $19,995.00 to $75,870.80 with an average price of $29,117.52. 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, ME?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,524.49. The average price has decreased by -1.9% since last year. The 213 for sale near Windsor, ME on CarGurus, range from $19,995 to $75,871 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in Windsor, ME have no reported accidents or damage?
182 out of 213 for sale near Windsor, ME 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 16 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 Truck Lease Deals in September 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
Best Car Deals in September 2026
In the market for a new or used car this year? Whether you’re looking to buy or lease, we’ve collated a list of the best car deals available this month.
CarGurus Editorial Team
Car Deals with 0% APR in September 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 Windsor MEChevrolet Silverado 1500 RST in Windsor MEChevrolet Silverado 1500 LTZ in Windsor MEChevrolet Silverado 1500 LT Trail Boss in Windsor MEChevrolet Silverado 1500 LT1 in Windsor MEChevrolet Silverado 1500 Custom in Windsor MEChevrolet Silverado 1500 High Country in Windsor MEChevrolet Silverado 1500 Custom Trail Boss in Windsor MEChevrolet Silverado 1500 Work Truck in Windsor ME
Chevrolet Silverado 1500 in Augusta MEChevrolet Silverado 1500 in Auburn MEChevrolet Silverado 1500 in Portland MEChevrolet Silverado 1500 in Portsmouth NHChevrolet Silverado 1500 in Manchester NHChevrolet Silverado 1500 in Montpelier VTChevrolet Silverado 1500 in Boston MAChevrolet Silverado 1500 in Groton MAChevrolet Silverado 1500 in Plymouth MA
Chevrolet Silverado 1500 in Windsor MEOld Chevy Trucks for Sale in Windsor MEClassic Muscle Cars for Sale in Windsor MEChevrolet Trucks For Sale in Windsor MECheap Muscle Cars for Sale in Windsor MEWork Trucks for Sale in Windsor MEReliable Cars For Sale in Windsor MEAmerican Made Trucks For Sale in Windsor MEBest Pickup Trucks For Sale in Windsor MEBest Cars Under $5,000 For Sale in Windsor ME
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 WindsorUsed SUVs / Crossovers for Sale with Low Mileage in WindsorUsed Hatchbacks for Sale with Low Mileage in WindsorUsed Convertibles for Sale with Low Mileage in WindsorUsed Vans for Sale with Low Mileage in WindsorUsed Minivans for Sale with Low Mileage in WindsorUsed Pickup Trucks for Sale with Low Mileage in WindsorUsed Coupes for Sale with Low Mileage in WindsorUsed Wagons for Sale with Low Mileage in Windsor
