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 Winamac, IN

403 results
Winamac, IN
2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD S&H Auto Group - Elkhart

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

100,692 miles

$29,710

Fair Deal
Elkhart, IN
60 mi away
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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
100,692
Stock number:
E301904
VIN:
1GCPYFED7KZ301904

Sponsored

2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

43,841 miles

$36,995

Fair Deal
Middlebury, IN
64 mi away
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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
43,841
Stock number:
A235725
VIN:
1GCPYFED5KZ235725

Sponsored

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

13,463 miles

$51,820

Good Deal
Michigan City, IN
46 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Blue
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
13,463
Stock number:
P1256
VIN:
3GCUDFEL9RG223089

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

136,386 miles

$26,799

Good Deal
Columbia City, IN
63 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:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
136,386
Stock number:
GM6640A
VIN:
1GCPYFELXMZ288527

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

31,555 miles

$36,700

Great Deal
Lafayette, IN
45 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
31,555
Stock number:
4004LP
VIN:
1GCPYFED8MZ353237

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

15,366 miles

$40,700

Good Deal
Merrillville, IN
48 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
15,366
Stock number:
P1099
VIN:
3GCPYFEDXMG434773

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

107,480 miles

$28,200

Good Deal
Brownsburg, IN
69 mi away
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:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
107,480
Stock number:
BCJ250264B
VIN:
3GCPYFED9KG268825

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

43,841 miles

$36,995

Fair Deal
Middlebury, IN
64 mi away
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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
43,841
Stock number:
A235725
VIN:
1GCPYFED5KZ235725

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

63,332 miles

$36,805

Good Deal
Huntington, IN
60 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
63,332
Stock number:
440-B348
VIN:
1GCPYFEL0NZ136094

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

37,672 miles

$37,546

Fair Deal
Kalamazoo, MI
99 mi away
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:
Cajun Red Tintcoat
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
37,672
Stock number:
T1318
VIN:
1GCPYFED7KZ412968

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

97,497 miles

$29,734

Good Deal
Rochester, IN
23 mi away
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
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Mileage:
97,497
Stock number:
R20366D
VIN:
1GCPYFED6KZ347045

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

42,527 miles

$37,634

Great Deal
Lafayette, IN
45 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
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
42,527
Stock number:
C46
VIN:
1GCPYFED4MZ260800

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

62,357 miles

$35,972

Good Deal
Bolingbrook, IL
86 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:
62,357
Stock number:
49459B
VIN:
3GCPYFEL8MG454706

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

72,708 miles

$33,400

Good Deal
Westmont, IL
87 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:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
72,708
Stock number:
D3373B
VIN:
1GCPYFED9MZ169568

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

35,321 miles

$38,694

Good Deal
Bridgeview, IL
77 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Northsky Blue Metallic
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
35,321
Stock number:
JP2804
VIN:
1GCPYFEL1NZ156676

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

36,444 miles

$36,475

Great Deal
Hicksville, OH
99 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:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
36,444
Stock number:
ZC25544
VIN:
1GCPYFED6MZ436214

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

74,862 miles

$33,395

Fair Deal
Glen Ellyn, IL
93 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
74,862
Stock number:
C71075AA
VIN:
1GCPYFED5LZ292976

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

28,557 miles

$42,000

Fair Deal
Chicago, IL
74 mi away
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:
Sterling Gray Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
28,557
Stock number:
P25301
VIN:
3GCPDFEK7PG362199

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT Trail Boss
  5. / Indiana
  6. / Winamac
  • Chevrolet Silverado 1500 LT in Winamac IN

  • Chevrolet Silverado 1500 RST in Winamac IN

  • Chevrolet Silverado 1500 LTZ in Winamac IN

  • Chevrolet Silverado 1500 LT Trail Boss in Winamac IN

  • Chevrolet Silverado 1500 LT1 in Winamac IN

  • Chevrolet Silverado 1500 Custom in Winamac IN

  • Chevrolet Silverado 1500 High Country in Winamac IN

  • Chevrolet Silverado 1500 Custom Trail Boss in Winamac IN

  • Chevrolet Silverado 1500 Work Truck in Winamac IN

  • Chevrolet Silverado 1500 in Lafayette IN

  • Chevrolet Silverado 1500 in Kokomo IN

  • Chevrolet Silverado 1500 in South Bend IN

  • Chevrolet Silverado 1500 in Crawfordsville IN

  • Chevrolet Silverado 1500 in Fort Wayne IN

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in Anderson IN

  • Chevrolet Silverado 1500 in Indianapolis IN

  • Chevrolet Silverado 1500 in Kalamazoo MI

  • Chevrolet Silverado 1500 in Winamac IN

  • Old Chevy Trucks for Sale in Winamac IN

  • Classic Muscle Cars for Sale in Winamac IN

  • Chevrolet Trucks For Sale in Winamac IN

  • Cheap Muscle Cars for Sale in Winamac IN

  • Work Trucks for Sale in Winamac IN

  • Reliable Cars For Sale in Winamac IN

  • American Made Trucks For Sale in Winamac IN

  • Best Pickup Trucks For Sale in Winamac IN

  • Best Cars Under $5,000 For Sale in Winamac IN

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Winamac IN

  • 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

  • Chevrolet of Merrillville

  • DeFOUW Chevrolet

  • Team Chevrolet

  • Shepherd's Chevrolet

  • Shepherd's Chevrolet GMC of Wabash Inc

  • Wiers Chevrolet GMC

  • Hubbard GM Center

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.