Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWinston, MT
68 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:
- 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:
- 29,589
- Stock #:
- 230
- VIN:
- 3GCUDCED4RG383761
New arrival
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,589 mi
Livingston, MT
76 mi away
Good Deal
$42,389
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Lakeshore Blue Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,315
- Stock #:
- 10735A
- VIN:
- 3GCPDCEK2RG256809
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,315 mi
Great Falls, MT
74 mi away
Good Deal
$36,954
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Red Hot
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $1,725 shipping
Good Deal
$33,960
- 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:
- 29,589
- Stock #:
- 230
- VIN:
- 3GCUDCED4RG383761
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,589 mi
Livingston, MT
76 mi away
Good Deal
$42,389
- 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:
- White
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 91,364
- Stock #:
- 3386
- VIN:
- 1GCPYCEL8NZ233672
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,364 mi
Home delivery from Yakima, WA
Price includes $416 shipping
Fair Deal
$31,311
- 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:
- GRY
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 62,918
- Stock #:
- 11258
- VIN:
- 3GCPDCED1NG673222
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,918 mi
Home delivery from Blackwood, NJ
Price includes $1,884 shipping
Fair Deal
$37,732
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 64,762
- Stock #:
- 676711TK
- VIN:
- 3GCPDCED9NG676711
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
64,762 mi
Home delivery from Billings, MT
Price includes $224 shipping
Good Deal
$36,144
- 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:
- Summit White
- Fuel type:
- Gasoline
- Mileage:
- 67,454
- Stock #:
- N849
- VIN:
- 1GCPYCEF3LZ260110
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
67,454 mi
Home delivery from Mount Vernon, WA
Price includes $777 shipping
Great Deal
$29,462
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,308
- Stock #:
- FBC0125A
- VIN:
- 3GCPKCEKXSG347497
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,308 mi
Home delivery from Ft Benton, MT
Price includes $135 shipping
Good Deal
$42,633
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 59,609
- Stock #:
- W167457
- VIN:
- 1GCPYCEF3LZ167457
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,609 mi
Home delivery from West Valley City, UT
Price includes $400 shipping
Good Deal
$32,027
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3,560
- Stock #:
- P25761
- VIN:
- 3GCPKCEK0TG160125
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
3,560 mi
Home delivery from Scottsdale, AZ
Price includes $1,260 shipping
Good Deal
$44,859
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 25,093
- Stock #:
- 46366A
- VIN:
- 3GCUDCEDXPG319723
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,093 mi
Home delivery from Jackson, WY
Price includes $275 shipping
Fair Deal
$42,103
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 119,092
- Stock #:
- F073
- VIN:
- 1GCPYCEF0MZ173587
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
119,092 mi
Home delivery from Painesville, OH
Price includes $3,072 shipping
Great Deal
$24,947
- 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
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 60,897
- Stock #:
- 102757
- VIN:
- 3GCUDCED0PG323361
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,897 mi
Home delivery from Albuquerque, NM
Price includes $1,650 shipping
Fair Deal
$39,398
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 4.3L V6 Flex Fuel Vehicle
- Exterior color:
- Red
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 51,860
- Stock #:
- G478752
- VIN:
- 3GCPYCEH0MG478752
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,860 mi
Home delivery from Houston, TX
Price includes $2,174 shipping
Good Deal
$33,896
- 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:
- 51,605
- Stock #:
- NG671158TC
- VIN:
- 3GCPDCED8NG671158
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,605 mi
Helena, MT
17 mi away
Fair Deal
$37,953
- 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:
- SAND DUNE METALLIC
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $1,307 shipping
Fair Deal
$32,912
- 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:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 68,105
- Stock #:
- 323339
- VIN:
- 1GCPDBEKXPZ323339
Price drop
-$2,500
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,105 mi
Home delivery from Orlando, FL
Price includes $2,054 shipping
Great Deal
$34,542
$32,042
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 83,704
- Stock #:
- 153965B
- VIN:
- 1GCPYCEF5MZ153965
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,704 mi
Home delivery from Dallas, TX
Price includes $1,228 shipping
Fair Deal
$31,953
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 70,388
- Stock #:
- 313046
- VIN:
- 3GCUDCED8PG313046
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,388 mi
Home delivery from Euless, TX
Price includes $2,192 shipping
Fair Deal
$37,864
- 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
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 61,142
- Stock #:
- 6-1339
- VIN:
- 3GCUDCED2RG163437
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
61,142 mi
Home delivery from Apache Junction, AZ
Price includes $904 shipping
Fair Deal
$40,503
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 144,887
- Stock #:
- 15203
- VIN:
- 1GCPYCEF3LZ260446
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
144,887 mi
Home delivery from Spokane, WA
Price includes $422 shipping
Fair Deal
$24,610
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 171,237
- Stock #:
- L2686A
- VIN:
- 1GCPYCEF7LZ269179
Price drop
-$1,600
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
171,237 mi
Home delivery from Post Falls, ID
Price includes $528 shipping
Good Deal
$22,123
$20,523
- 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:
- White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 99,983
- Stock #:
- 112803
- VIN:
- 1GCPYCEF5KZ296850
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
99,983 mi
Home delivery from Redford, MI
Price includes $1,418 shipping
Fair Deal
$28,717
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Winston, MT?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,072.10. The average price has decreased by -0.8% since last year. The 66 for sale near Winston, MT on CarGurus, range from $20,523 to $64,455 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Winston, MT have no reported accidents or damage?
57 out of 66 for sale near Winston, MT have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
Relevant articles
CarGurus Editorial Team
Car Deals with 0% APR in July 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.
CarGurus Editorial Team
Best Truck Lease Deals in July 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 July 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.
Chevrolet Silverado 1500 LT in Winston MTChevrolet Silverado 1500 RST in Winston MTChevrolet Silverado 1500 LTZ in Winston MTChevrolet Silverado 1500 LT Trail Boss in Winston MTChevrolet Silverado 1500 LT1 in Winston MTChevrolet Silverado 1500 Custom in Winston MTChevrolet Silverado 1500 High Country in Winston MTChevrolet Silverado 1500 Custom Trail Boss in Winston MTChevrolet Silverado 1500 Work Truck in Winston MT
Chevrolet Silverado 1500 in Helena MTChevrolet Silverado 1500 in Butte MTChevrolet Silverado 1500 in Bozeman MTChevrolet Silverado 1500 in Great Falls MTChevrolet Silverado 1500 in Missoula MTChevrolet Silverado 1500 in Billings MTChevrolet Silverado 1500 in Kalispell MTChevrolet Silverado 1500 in Rexburg IDChevrolet Silverado 1500 in Idaho Falls ID
Chevrolet Silverado 1500 in Winston MTOld Chevy Trucks for Sale in Winston MTClassic Muscle Cars for Sale in Winston MTChevrolet Trucks For Sale in Winston MTCheap Muscle Cars for Sale in Winston MTWork Trucks for Sale in Winston MTReliable Cars For Sale in Winston MTAmerican Made Trucks For Sale in Winston MTBest Pickup Trucks For Sale in Winston MTBest Cars Under $5,000 For Sale in Winston MT
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 WinstonUsed SUVs / Crossovers for Sale with Low Mileage in WinstonUsed Hatchbacks for Sale with Low Mileage in WinstonUsed Convertibles for Sale with Low Mileage in WinstonUsed Vans for Sale with Low Mileage in WinstonUsed Minivans for Sale with Low Mileage in WinstonUsed Pickup Trucks for Sale with Low Mileage in WinstonUsed Coupes for Sale with Low Mileage in WinstonUsed Wagons for Sale with Low Mileage in Winston
