Used Chevrolet Silverado 1500 LT Trail Boss for Sale near East Hampton, NY
324 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 117,219
- Stock #:
- 1902
- VIN:
- 1GCPYFED2KZ362061
Sponsored by S & D Auto Sales - West Bridgewater
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
117,219 mi
West Bridgewater, MA
98 mi away
Good Deal
$26,586
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 66,358
- Stock #:
- S26321A
- VIN:
- 1GCPYFED7MZ129280
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
66,358 mi
North Dartmouth, MA
81 mi away
Good Deal
$35,097
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Glacier Blue Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 36,200
- Stock #:
- TT0537A
- VIN:
- 3GCUDFE87PG248498
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
36,200 mi
New London, CT
30 mi away
Fair Deal
$44,540
- 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:
- Cypress Gray
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 13,611
- Stock #:
- 9418HU
- VIN:
- 3GCUKFED3SG185136
2025 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
13,611 mi
Southampton, NY
8 mi away
Fair Deal
$52,392
- 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
62 mi away
Great Deal
$31,049
$28,599
- 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:
- 49,933
- Stock #:
- P19332A
- VIN:
- 3GCPDFEK8NG510132
New arrival
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
49,933 mi
Mendon, MA
88 mi away
Good Deal
$35,467
- 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
Price drop
-$5,000
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
104,003 mi
Auburn, MA
88 mi away
Great Deal
$30,294
$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:
- 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 $1,113 shipping
Great Deal
$30,105
- 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
55 mi away
Fair Deal
$28,793
- 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
57 mi away
Great Deal
$24,688
- 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 $252 shipping
Good Deal
$37,195
$36,377
- 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
-$2,505
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
67,817 mi
Wappingers Falls, NY
98 mi away
Great Deal
$31,675
$29,170
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 128,344
- Stock #:
- C4123
- VIN:
- 1GCPYFED5KZ235501
2019 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
128,344 mi
North Attleboro, MA
86 mi away
Great Deal
$24,693
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Gray (Satin Steel Metallic)
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 64,153
- Stock #:
- GM3870
- VIN:
- 1GCPYFED9NZ207009
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
64,153 mi
Westborough, MA
99 mi away
Good Deal
$34,590
- 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
53 mi away
Great Deal
$31,625
$30,124
- 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:
- Cherry Red Tintcoat
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 90,645
- Stock #:
- SG6377A
- VIN:
- 3GCUDFED0NG583015
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
90,645 mi
Raynham, MA
93 mi away
Good Deal
$33,682
- 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:
- Gideon/Very Dark Atm
- Transmission:
- Automatic
- Mileage:
- 129,834
- Stock #:
- M-393655
- VIN:
- 3GCPYFED6MG393655
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
129,834 mi
East Windsor, CT
68 mi away
Good Deal
$25,850
- 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 $399 shipping
Good Deal
$33,394
$32,394
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 98,622
- Stock #:
- CC60506A
- VIN:
- 3GCUDFED6NG671289
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
98,622 mi
Home delivery from Hyannis, MA
Free home delivery
Good Deal
$33,426
- 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
Price drop
-$1,000
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
105,491 mi
Palmer, MA
85 mi away
Good Deal
$28,771
$27,771
- 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
47 mi away
Fair Deal
$44,996
- 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:
- 124,861
- Stock #:
- P4454A
- VIN:
- 1GCPYFED9LZ205404
2020 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
124,861 mi
Cranston, RI
69 mi away
Fair Deal
$28,299
- 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
57 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:
- 355 hp 5.3L V8
- Exterior color:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 71,217
- Stock #:
- 26-720A
- VIN:
- 3GCUDFED8NG571971
Sponsored Listing
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
71,217 mi
Torrington, CT
76 mi away
Good Deal
$36,876
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 $21,362.50 to $72,604.40 with an average price of $28,743.06. 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 East Hampton, NY?
The average Chevrolet Silverado 1500 LT Trail Boss costs about $26,175.04. The average price has decreased by -4.1% since last year. The 256 for sale near East Hampton, NY on CarGurus, range from $21,362 to $72,604 in price.
How many Chevrolet Silverado 1500 LT Trail Boss vehicles in East Hampton, NY have no reported accidents or damage?
242 out of 256 for sale near East Hampton, NY 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
Drew Johnson
The Cheapest New Trucks on Sale in 2026
Is there such a thing as a cheap new truck any more? Absolutely! Here's our expert guide to the top 10 cheapest new trucks on sale.
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
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Chevrolet Silverado 1500 LT in East Hampton NYChevrolet Silverado 1500 RST in East Hampton NYChevrolet Silverado 1500 LTZ in East Hampton NYChevrolet Silverado 1500 LT Trail Boss in East Hampton NYChevrolet Silverado 1500 LT1 in East Hampton NYChevrolet Silverado 1500 Custom in East Hampton NYChevrolet Silverado 1500 High Country in East Hampton NYChevrolet Silverado 1500 Custom Trail Boss in East Hampton NYChevrolet Silverado 1500 Work Truck in East Hampton NY
Chevrolet Silverado 1500 in New Haven CTChevrolet Silverado 1500 in Holtsville NYChevrolet Silverado 1500 in Hartford CTChevrolet Silverado 1500 in Stamford CTChevrolet Silverado 1500 in Providence RIChevrolet Silverado 1500 in New Bedford MAChevrolet Silverado 1500 in Chicopee MAChevrolet Silverado 1500 in Worcester MAChevrolet Silverado 1500 in New York NY
Chevrolet Silverado 1500 in East Hampton NYOld Chevy Trucks for Sale in East Hampton NYClassic Muscle Cars for Sale in East Hampton NYChevrolet Trucks For Sale in East Hampton NYCheap Muscle Cars for Sale in East Hampton NYWork Trucks for Sale in East Hampton NYReliable Cars For Sale in East Hampton NYAmerican Made Trucks For Sale in East Hampton NYBest Pickup Trucks For Sale in East Hampton NYBest Cars Under $5,000 For Sale in East Hampton NY
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 East HamptonUsed SUVs / Crossovers for Sale with Low Mileage in East HamptonUsed Hatchbacks for Sale with Low Mileage in East HamptonUsed Convertibles for Sale with Low Mileage in East HamptonUsed Vans for Sale with Low Mileage in East HamptonUsed Minivans for Sale with Low Mileage in East HamptonUsed Pickup Trucks for Sale with Low Mileage in East HamptonUsed Coupes for Sale with Low Mileage in East HamptonUsed Wagons for Sale with Low Mileage in East Hampton
