Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWoodruff, WI
88 vehicles found
- 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:
- Red
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 74,770
- Stock #:
- PT0150
- VIN:
- 1GCRYCEF5KZ198247
Price drop
-$950
Sponsored by Car Smart
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
74,770 mi
Wausau, WI
71 mi away
Great Deal
$27,149
$26,199
- 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
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 50,224
- Stock #:
- H1977A
- VIN:
- 3GCPYCEL6NG197402
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,224 mi
Wausau, WI
72 mi away
Great Deal
$31,295
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 76,938
- Stock #:
- 38210A
- VIN:
- 1GCPYCEF5KZ177776
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,938 mi
Merrill, WI
54 mi away
Fair Deal
$30,990
- 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:
- Mosaic Black Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,771
- Stock #:
- 5048
- VIN:
- 1GCPYCEL5NZ100710
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,771 mi
Home delivery from Seffner, FL
Price includes $1,369 shipping
Great Deal
$33,363
- 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:
- Red
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 74,770
- Stock #:
- PT0150
- VIN:
- 1GCRYCEF5KZ198247
Price drop
-$950
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
74,770 mi
Wausau, WI
71 mi away
Great Deal
$27,149
$26,199
- 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
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 33,262
- Stock #:
- MX4598
- VIN:
- 1GCPYCEF4MZ232253
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,262 mi
Home delivery from Michigan Center, MI
Price includes $664 shipping
Fair Deal
$37,297
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 62,775
- Stock #:
- 5019
- VIN:
- 1GCPYCEF0LZ168095
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $360 shipping
Great Deal
$29,760
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 48,294
- Stock #:
- 260584A
- VIN:
- 1GCPYCEF0LZ196270
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
48,294 mi
Houghton, MI
95 mi away
Good Deal
$32,999
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,768
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,768 mi
Home delivery from Pleasantville, NJ
Price includes $1,626 shipping
Good Deal
$36,366
- 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:
- Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 26,322
- Stock #:
- 48208
- VIN:
- 3GCUDCED4PG360459
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
26,322 mi
Home delivery from Arlington, TX
Price includes $1,497 shipping
Great Deal
$38,717
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 104,499
- Stock #:
- 14237
- VIN:
- 1GCPYCEF8MZ381894
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,499 mi
Home delivery from Rogers, MN
Price includes $394 shipping
Fair Deal
$29,443
- 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
Price drop
-$1,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
3,560 mi
Home delivery from Scottsdale, AZ
Price includes $2,040 shipping
Good Deal
$46,639
$45,639
- Year:
- 2020
- 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:
- 58,244
- Stock #:
- J1686B
- VIN:
- 1GCPYCEL4LZ356446
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,244 mi
Rhinelander, WI
26 mi away
Good Deal
$34,449
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 46,774
- Stock #:
- S19825A
- VIN:
- 3GCUDCED7RG267941
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,774 mi
Home delivery from Newton, NC
Price includes $1,256 shipping
Fair Deal
$42,254
- 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 $1,782 shipping
Fair Deal
$37,454
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,520
- Stock #:
- 260563A
- VIN:
- 3GCPDCEK6RG211470
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,520 mi
Houghton, MI
95 mi away
Fair Deal
$41,983
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Red
- Fuel type:
- Diesel
- Interior color:
- Black
- Mileage:
- 110,590
- Stock #:
- 301317
- VIN:
- 3GCUDCE84PG301317
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,590 mi
Home delivery from Euless, TX
Price includes $1,485 shipping
Good Deal
$30,480
- 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 $1,752 shipping
Good Deal
$33,475
- Year:
- 2020
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 82,600
- Stock #:
- T0131A
- VIN:
- 1GCPYCEH9LZ164032
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,600 mi
Home delivery from Canal Fulton, OH
Price includes $802 shipping
Good Deal
$27,048
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 95,901
- Stock #:
- 110261TK
- VIN:
- 1GCPYCEF9LZ110261
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
95,901 mi
Home delivery from Noblesville, IN
Price includes $674 shipping
Fair Deal
$28,838
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 16,913
- Stock #:
- R87954
- VIN:
- 3GCUKCED9SG358155
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
16,913 mi
Home delivery from Herculaneum, MO
Price includes $1,066 shipping
Fair Deal
$47,247
- 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
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,704 mi
Home delivery from Dallas, TX
Price includes $986 shipping
Fair Deal
$31,711
- 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
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,609 mi
Home delivery from West Valley City, UT
Price includes $1,173 shipping
Fair Deal
$32,800
- 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 $1,445 shipping
Fair Deal
$41,044
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Woodruff, WI?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,150.94. The average price has decreased by -1.4% since last year. The 85 for sale near Woodruff, WI on CarGurus, range from $21,054 to $59,747 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Woodruff, WI have no reported accidents or damage?
75 out of 85 for sale near Woodruff, WI 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
The Best Pickup Trucks of 2026, Ranked
Pickup truck competition is fierce and change is in the air. Electric trucks and compact pickups are hitting the market, providing new choices for both small businesses and weekend adventurers. But which truck suits your needs best?
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.
Craig Fitzgerald
The Best Trucks Under $25,000 in 2026
New trucks cost more than ever, but the prices of used ones finally seem to be cooling. You still can't find the latest and fanciest full-sizes for budget prices, but fortunately, there are plenty of good trucks under $25,000 these days. Here, we've assembled a list of the best.
Chevrolet Silverado 1500 LT in Woodruff WIChevrolet Silverado 1500 RST in Woodruff WIChevrolet Silverado 1500 LTZ in Woodruff WIChevrolet Silverado 1500 LT Trail Boss in Woodruff WIChevrolet Silverado 1500 LT1 in Woodruff WIChevrolet Silverado 1500 Custom in Woodruff WIChevrolet Silverado 1500 High Country in Woodruff WIChevrolet Silverado 1500 Custom Trail Boss in Woodruff WIChevrolet Silverado 1500 Work Truck in Woodruff WI
Chevrolet Silverado 1500 in Marshfield WIChevrolet Silverado 1500 in Eau Claire WIChevrolet Silverado 1500 in Green Bay WIChevrolet Silverado 1500 in Appleton WIChevrolet Silverado 1500 in Duluth MNChevrolet Silverado 1500 in Fond du Lac WIChevrolet Silverado 1500 in La Crosse WIChevrolet Silverado 1500 in Minneapolis MNChevrolet Silverado 1500 in Rochester MN
Chevrolet Silverado 1500 in Woodruff WIOld Chevy Trucks for Sale in Woodruff WIClassic Muscle Cars for Sale in Woodruff WIChevrolet Trucks For Sale in Woodruff WICheap Muscle Cars for Sale in Woodruff WIWork Trucks for Sale in Woodruff WIReliable Cars For Sale in Woodruff WIAmerican Made Trucks For Sale in Woodruff WIBest Pickup Trucks For Sale in Woodruff WIBest Cars Under $5,000 For Sale in Woodruff WI
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 WoodruffUsed SUVs / Crossovers for Sale with Low Mileage in WoodruffUsed Hatchbacks for Sale with Low Mileage in WoodruffUsed Convertibles for Sale with Low Mileage in WoodruffUsed Vans for Sale with Low Mileage in WoodruffUsed Minivans for Sale with Low Mileage in WoodruffUsed Pickup Trucks for Sale with Low Mileage in WoodruffUsed Coupes for Sale with Low Mileage in WoodruffUsed Wagons for Sale with Low Mileage in Woodruff
