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 Rubicon, WI

150 results
Rubicon, WI
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Lake Chevrolet

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,189 miles

$31,965

Good Deal
Certified Pre-Owned
Milwaukee, WI
35 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:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
67,189
Stock number:
C19637N
VIN:
1GCPYCEF4MZ406287

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,064 miles

$43,617

Great Deal
West Bend, WI
15 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Summit White
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
4,064
Stock number:
T68060A
VIN:
3GCUDCE82RG103161

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,310 miles

$34,979

Fair Deal
Milton, WI
44 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
48,310
Stock number:
1975
VIN:
1GCPYCEF9LZ316924

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,189 miles

$31,965

Good Deal
Certified Pre-Owned
Milwaukee, WI
35 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:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
67,189
Stock number:
C19637N
VIN:
1GCPYCEF4MZ406287

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,599 miles

$32,700

Great Deal
Certified Pre-Owned
Madison, WI
43 mi away
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:
Black
Transmission:
Automatic
Mileage:
54,599
Stock number:
MZ339996
VIN:
1GCPYCEL7MZ339996

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,310 miles

$34,979

Fair Deal
Milton, WI
44 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
48,310
Stock number:
1975
VIN:
1GCPYCEF9LZ316924

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,881 miles

$30,500

Good Deal
Sheboygan, WI
44 mi away
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:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
65,881
Stock number:
D414867T
VIN:
1GCPYCEH5MZ383894

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,843 miles

$37,999

Fair Deal
Fond Du Lac, WI
31 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior color:
Sand Dune Metallic
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
40,843
Stock number:
16157ZA
VIN:
3GCUDCET3NG501798

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,172 miles

$40,999

Good Deal
Plymouth, WI
40 mi away
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 (gba)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black (h0u)
Transmission:
Automatic
Mileage:
18,172
Stock number:
9753
VIN:
3GCUDCED9RG306982

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

121,739 miles

$24,837

Good Deal
Sun Prairie, WI
40 mi away
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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
121,739
Stock number:
71590
VIN:
1GCPYCEH5MZ318592

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

97,438 miles

$27,491

Good Deal
Fond du Lac, WI
31 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
97,438
Stock number:
DB34500
VIN:
1GCPYCEF8LZ119582

Sponsored

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

  • Chevrolet Silverado 1500 RST in Rubicon WI

  • Chevrolet Silverado 1500 LTZ in Rubicon WI

  • Chevrolet Silverado 1500 LT Trail Boss in Rubicon WI

  • Chevrolet Silverado 1500 LT1 in Rubicon WI

  • Chevrolet Silverado 1500 High Country in Rubicon WI

  • Chevrolet Silverado 1500 Custom in Rubicon WI

  • Chevrolet Silverado 1500 Custom Trail Boss in Rubicon WI

  • Chevrolet Silverado 1500 Work Truck in Rubicon WI

  • Chevrolet Silverado 1500 in Fond du Lac WI

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Appleton WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Green Bay WI

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Rubicon WI

  • Old Chevy Trucks for Sale in Rubicon WI

  • Classic Muscle Cars for Sale in Rubicon WI

  • Chevrolet Trucks For Sale in Rubicon WI

  • Cheap Muscle Cars for Sale in Rubicon WI

  • Work Trucks for Sale in Rubicon WI

  • Reliable Cars For Sale in Rubicon WI

  • American Made Trucks For Sale in Rubicon WI

  • Best Pickup Trucks For Sale in Rubicon WI

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Rubicon 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

  • Lake Chevrolet

  • Sheboygan Chevrolet GMC

  • Kunes Hope Chevrolet

  • Eric von Schledorn Saukville

  • Boucher Volkswagen Marketplace

  • Newman Chevrolet of Cedarburg

  • Heiser Chevrolet of West Bend

  • Lynch Chevrolet Mukwonago

  • Napleton Chevrolet Columbus

  • Homan Chevrolet GMC of Ripon

  • Homan Chevrolet Buick

  • Roger Palmen Chevrolet

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

© 2026 CarGurus, Inc., All Rights Reserved.