CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Woodruff, WI

102 results
Woodruff, WI
2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Dahl Chrysler Dodge Jeep Ram Stevens Point

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,424 miles

$32,495

Good Deal
Stevens Point, WI
99 mi away
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:
Silver Ice Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
55,424
Stock number:
EB0096
VIN:
1GCPYCEF2LZ142341

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,942 miles

$36,574

Good Deal
Minocqua, WI
7 mi away
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:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
19,942
Stock number:
260092A
VIN:
1GCPYCEF6MZ315585

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,370 miles

$28,890

Good Deal
Eagle River, WI
22 mi away
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:
92,370
Stock number:
F2903A
VIN:
1GCPYCEF1LZ358696

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,793 miles

$33,270

Good Deal
Wausau, WI
72 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Cherry Red
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
45,793
Stock number:
E10623
VIN:
1GCPYCEK9NZ138657

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,942 miles

$36,574

Good Deal
Minocqua, WI
7 mi away
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:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
19,942
Stock number:
260092A
VIN:
1GCPYCEF6MZ315585

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,370 miles

$28,890

Good Deal
Eagle River, WI
22 mi away
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:
92,370
Stock number:
F2903A
VIN:
1GCPYCEF1LZ358696

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,558 miles

$39,995

Fair Deal
Certified Pre-Owned
Antigo, WI
61 mi away
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:
Harvest Bronze Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
41,558
Stock number:
S334A
VIN:
3GCUDCED5PG360051

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,424 miles

$32,495

Good Deal
Stevens Point, WI
99 mi away
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:
Silver Ice Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
55,424
Stock number:
EB0096
VIN:
1GCPYCEF2LZ142341

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Wisconsin
  6. / Woodruff
  • Chevrolet Silverado 1500 LT in Woodruff WI

  • Chevrolet Silverado 1500 RST in Woodruff WI

  • Chevrolet Silverado 1500 LTZ in Woodruff WI

  • Chevrolet Silverado 1500 LT Trail Boss in Woodruff WI

  • Chevrolet Silverado 1500 LT1 in Woodruff WI

  • Chevrolet Silverado 1500 Custom in Woodruff WI

  • Chevrolet Silverado 1500 High Country in Woodruff WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Woodruff WI

  • Chevrolet Silverado 1500 Work Truck in Woodruff WI

  • Chevrolet Silverado 1500 in Marshfield WI

  • Chevrolet Silverado 1500 in Eau Claire WI

  • Chevrolet Silverado 1500 in Green Bay WI

  • Chevrolet Silverado 1500 in Appleton WI

  • Chevrolet Silverado 1500 in Duluth MN

  • Chevrolet Silverado 1500 in Fond du Lac WI

  • Chevrolet Silverado 1500 in La Crosse WI

  • Chevrolet Silverado 1500 in Minneapolis MN

  • Chevrolet Silverado 1500 in Rochester MN

  • Chevrolet Silverado 1500 in Woodruff WI

  • Old Chevy Trucks for Sale in Woodruff WI

  • Classic Muscle Cars for Sale in Woodruff WI

  • Chevrolet Trucks For Sale in Woodruff WI

  • Cheap Muscle Cars for Sale in Woodruff WI

  • Work Trucks for Sale in Woodruff WI

  • Reliable Cars For Sale in Woodruff WI

  • American Made Trucks For Sale in Woodruff WI

  • Best Pickup Trucks For Sale in Woodruff WI

  • Best Cars Under $5,000 For Sale in Woodruff WI

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Woodruff WI

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Minocqua Chevrolet

  • Rhinelander GM Auto Group

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2025 CarGurus, Inc., All Rights Reserved.