Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWinnetka, CA
79 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Silver
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 57,462
- Stock #:
- 159645
- VIN:
- 3GCPYCEK8NG159645
New arrival
Sponsored by Regency USA Inc
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,462 mi
Wilmington, CA
35 mi away
Good Deal
$32,885
- 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:
- 110,574
- Stock #:
- 286931
- VIN:
- 3GCPYCEF3MG286031
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,574 mi
Canoga Park, CA
1 mi away
Good Deal
$27,335
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 90,811
- Stock #:
- TV27438
- VIN:
- 1GCPYCEF6MZ246669
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
90,811 mi
Van Nuys, CA
7 mi away
Good Deal
$29,622
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 101,648
- Stock #:
- 2735PB
- VIN:
- 1GCPYCEF6LZ163144
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
101,648 mi
Simi Valley, CA
13 mi away
Fair Deal
$28,722
- 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:
- 5,141
- Stock #:
- 261407A
- VIN:
- 3GCPKCEK9TG202842
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
5,141 mi
Northridge, CA
4 mi away
Great Deal
$43,039
- 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:
- 58,240
- Stock #:
- CAP0177
- VIN:
- 3GCUDCED3PG324634
Price drop
-$1,000
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,240 mi
Long Beach, CA
35 mi away
Great Deal
$36,117
$35,117
- 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:
- 8-Speed Automatic
- Mileage:
- 101,123
- Stock #:
- 178541
- VIN:
- 3GCPYCEK3NG178541
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
101,123 mi
Canoga Park, CA
1 mi away
Good Deal
$27,085
- 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:
- 110,574
- Stock #:
- 286931
- VIN:
- 3GCPYCEF3MG286031
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,574 mi
Canoga Park, CA
1 mi away
Good Deal
$27,335
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 111,354
- VIN:
- 3GCPYCEF9KG199151
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
111,354 mi
Fullerton, CA
43 mi away
Good Deal
$24,233
- 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 (Steel Metallic)
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 117,302
- Stock #:
- 260818A
- VIN:
- 3GCPYCEF9MG146503
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
117,302 mi
Simi Valley, CA
13 mi away
Fair Deal
$28,600
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 54,368
- Stock #:
- EDM003C
- VIN:
- 1GCPYCEF7MZ440854
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,368 mi
Pacoima, CA
10 mi away
Fair Deal
$35,495
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 18,321
- Stock #:
- P10475
- VIN:
- 3GCUKCED8SG184059
Price drop
-$1,040
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
18,321 mi
Home delivery from Riverside, CA
Price includes $110 shipping
Good Deal
$44,091
$43,050
- 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:
- Silver
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 57,462
- Stock #:
- 159645
- VIN:
- 3GCPYCEK8NG159645
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,462 mi
Wilmington, CA
35 mi away
Good Deal
$32,885
- 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:
- 22,337
- Stock #:
- 59730
- VIN:
- 3GCPDCEK2PG304581
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,337 mi
Home delivery from Fontana, CA
Price includes $128 shipping
Good Deal
$37,208
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 90,811
- Stock #:
- TV27438
- VIN:
- 1GCPYCEF6MZ246669
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
90,811 mi
Van Nuys, CA
7 mi away
Good Deal
$29,622
- 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 $871 shipping
Fair Deal
$31,766
- 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:
- Sterling Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 28,519
- Stock #:
- 62057
- VIN:
- 3GCPDCEK9RG151586
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,519 mi
Home delivery from Costa Mesa, CA
Price includes $104 shipping
Great Deal
$37,184
- Year:
- 2026
- 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:
- 14,620
- Stock #:
- TTG196475
- VIN:
- 3GCUKCED3TG196475
New arrival
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
14,620 mi
Pasadena, CA
29 mi away
Good Deal
$45,084
- 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 $577 shipping
Good Deal
$32,204
- 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 $539 shipping
Good Deal
$44,138
- 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 $4,166 shipping
Good Deal
$26,041
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2,597
- Stock #:
- FP46197
- VIN:
- 3GCPDCEK9RG346197
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,597 mi
Los Angeles, CA
21 mi away
Fair Deal
$43,235
- 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 $1,366 shipping
Fair Deal
$39,114
- 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:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 54,368
- Stock #:
- EDM003C
- VIN:
- 1GCPYCEF7MZ440854
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,368 mi
Pacoima, CA
10 mi away
Fair Deal
$35,495
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Winnetka, CA?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,073.80. The average price has decreased by -0.7% since last year. The 79 for sale near Winnetka, CA on CarGurus, range from $21,871 to $64,540 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Winnetka, CA have no reported accidents or damage?
79 out of 79 for sale near Winnetka, CA 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 Winnetka CAChevrolet Silverado 1500 RST in Winnetka CAChevrolet Silverado 1500 LTZ in Winnetka CAChevrolet Silverado 1500 LT Trail Boss in Winnetka CAChevrolet Silverado 1500 LT1 in Winnetka CAChevrolet Silverado 1500 Custom in Winnetka CAChevrolet Silverado 1500 High Country in Winnetka CAChevrolet Silverado 1500 Custom Trail Boss in Winnetka CAChevrolet Silverado 1500 Work Truck in Winnetka CA
Chevrolet Silverado 1500 in Santa Clarita CAChevrolet Silverado 1500 in Malibu CAChevrolet Silverado 1500 in Los Angeles CAChevrolet Silverado 1500 in Ventura CAChevrolet Silverado 1500 in Lancaster CAChevrolet Silverado 1500 in Pomona CAChevrolet Silverado 1500 in Irvine CAChevrolet Silverado 1500 in Santa Barbara CAChevrolet Silverado 1500 in San Bernardino CA
Chevrolet Silverado 1500 in Winnetka CAOld Chevy Trucks for Sale in Winnetka CAClassic Muscle Cars for Sale in Winnetka CAChevrolet Trucks For Sale in Winnetka CACheap Muscle Cars for Sale in Winnetka CAWork Trucks for Sale in Winnetka CAReliable Cars For Sale in Winnetka CAAmerican Made Trucks For Sale in Winnetka CABest Pickup Trucks For Sale in Winnetka CABest Cars Under $5,000 For Sale in Winnetka CA
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 WinnetkaUsed SUVs / Crossovers for Sale with Low Mileage in WinnetkaUsed Hatchbacks for Sale with Low Mileage in WinnetkaUsed Convertibles for Sale with Low Mileage in WinnetkaUsed Vans for Sale with Low Mileage in WinnetkaUsed Minivans for Sale with Low Mileage in WinnetkaUsed Pickup Trucks for Sale with Low Mileage in WinnetkaUsed Coupes for Sale with Low Mileage in WinnetkaUsed Wagons for Sale with Low Mileage in Winnetka
