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 LT Trail Boss for Sale near New Berlin, WI

298 results
New Berlin, WI
2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Jon Green Family Auto

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

78,092 miles

$34,779

Fair Deal
Milton, WI
44 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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
78,092
Stock number:
1610A
VIN:
1GCPYFED3MZ124903

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

70,868 miles

$34,795

Fair Deal
Mount Pleasant, WI
19 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
70,868
Stock number:
P12893A
VIN:
1GCPYFED4MZ170692

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

68,199 miles

$33,789

Great Deal
Gurnee, IL
41 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
White
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
68,199
Stock number:
GM30035
VIN:
1GCPYFED1NZ172840

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,361 miles

$37,977

Fair Deal
Certified Pre-Owned
Milwaukee, WI
8 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,361
Stock number:
C19605NC
VIN:
1GCPYFED0LZ297695

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

54,130 miles

$44,197

Good Deal
Store transfer to Waukesha, WI
431 mi away • Price includes $199 shipping Price includes $199 shipping
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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
54,130
Stock number:
27860462
VIN:
3GCUDFED5RG281189

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

10,115 miles

$46,918

Good Deal
Certified Pre-Owned
Cedarburg, WI
24 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10,115
Stock number:
26131A
VIN:
3GCUDFEL4NG505103

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

43,657 miles

$39,992

Fair Deal
Kenosha, WI
28 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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
43,657
Stock number:
P13827
VIN:
1GCPYFED4MZ111142

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

84,985 miles

$32,840

Good Deal
Janesville, WI
48 mi away
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:
Black
Transmission:
Automatic
Mileage:
84,985
Stock number:
KL294
VIN:
1GCPYFEL5LZ350835

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

51,848 miles

$39,989

Great Deal
Johnson Creek, WI
36 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:
Red Hot
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
51,848
Stock number:
9350
VIN:
3GCUDFET3NG544958

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,918 miles

$36,197

Fair Deal
Store transfer to Waukesha, WI
993 mi away • Price includes $1,199 shipping Price includes $1,199 shipping
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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
59,918
Stock number:
26369538
VIN:
1GCPYFED8LZ322438

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

70,944 miles

$34,700

Fair Deal
Mchenry, IL
46 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:
Gray (Steel Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
70,944
Stock number:
UT20754
VIN:
1GCPYFED1LZ280064

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

84,985 miles

$32,840

Good Deal
Janesville, WI
48 mi away
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:
Black
Transmission:
Automatic
Mileage:
84,985
Stock number:
KL294
VIN:
1GCPYFEL5LZ350835

Sponsored

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

  • Chevrolet Silverado 1500 RST in New Berlin WI

  • Chevrolet Silverado 1500 LTZ in New Berlin WI

  • Chevrolet Silverado 1500 LT Trail Boss in New Berlin WI

  • Chevrolet Silverado 1500 LT1 in New Berlin WI

  • Chevrolet Silverado 1500 Custom in New Berlin WI

  • Chevrolet Silverado 1500 High Country in New Berlin WI

  • Chevrolet Silverado 1500 Custom Trail Boss in New Berlin WI

  • Chevrolet Silverado 1500 Work Truck in New Berlin WI

  • Chevrolet Silverado 1500 in Milwaukee WI

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Janesville WI

  • Chevrolet Silverado 1500 in Fond du Lac WI

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Madison WI

  • Chevrolet Silverado 1500 in Rockford IL

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in New Berlin WI

  • Old Chevy Trucks for Sale in New Berlin WI

  • Classic Muscle Cars for Sale in New Berlin WI

  • Chevrolet Trucks For Sale in New Berlin WI

  • Cheap Muscle Cars for Sale in New Berlin WI

  • Work Trucks for Sale in New Berlin WI

  • Reliable Cars For Sale in New Berlin WI

  • American Made Trucks For Sale in New Berlin WI

  • Best Pickup Trucks For Sale in New Berlin WI

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in New Berlin 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

  • Ray Chevrolet

  • Kayser Chevrolet Buick GMC

  • Lake Chevrolet

  • Kunes Hope Chevrolet

  • Eric von Schledorn Saukville

  • Boucher Volkswagen Marketplace

  • Heiser Chevrolet of West Bend

  • Lynch Chevrolet of Kenosha

  • Libertyville Chevrolet

  • Heiser Chevrolet, Inc.

  • Woodstock Chevrolet

  • Newman Chevrolet of Cedarburg

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.