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 Winamac, IN

196 results
Winamac, IN
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Advantage Chevrolet Bolingbrook

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,159 miles

$38,972

Fair Deal
Certified Pre-Owned
Bolingbrook, IL
86 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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,159
Stock number:
49138A
VIN:
3GCPDCEK1PG339273

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,672 miles

$38,996

Fair Deal
Certified Pre-Owned
Daleville, IN
86 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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,672
Stock number:
A8869
VIN:
3GCPDCEK3PG129581

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,704 miles

$31,997

Great Deal
Orland Park, IL
74 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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
50,704
Stock number:
B10901
VIN:
1GCPYCEF7MZ410785

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,839 miles

$33,972

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:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
42,839
Stock number:
VP1070A
VIN:
1GCPYCEF3MZ333171

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,200 miles

$35,000

Good Deal
Hicksville, OH
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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
26,200
Stock number:
ZC25727
VIN:
1GCPYCEF2LZ226126

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,975 miles

$32,049

Great Deal
Lafayette, IN
45 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
42,975
Stock number:
C129
VIN:
1GCPYCEF8LZ282796

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,741 miles

$35,540

Fair 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:
Red
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
41,741
Stock number:
Q499
VIN:
1GCPYCEFXMZ252555

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,420 miles

$26,232

Fair Deal
Certified Pre-Owned
Melrose Park, IL
87 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 (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
118,420
Stock number:
60890A
VIN:
1GCPYCEF4LZ171792

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,732 miles

$34,828

Good Deal
Villa Park, IL
90 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:
Jet Black
Transmission:
Automatic
Mileage:
31,732
Stock number:
B46674A
VIN:
1GCPYCEF7MZ292172

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,159 miles

$38,972

Fair Deal
Certified Pre-Owned
Bolingbrook, IL
86 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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,159
Stock number:
49138A
VIN:
3GCPDCEK1PG339273

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,168 miles

$35,977

Fair Deal
Elk Grove Village, IL
98 mi away
Year:
2022
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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,168
Stock number:
NC3632
VIN:
3GCPDCEK3NG583388

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,460 miles

$28,159

Good Deal
Noblesville, IN
80 mi away
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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
72,460
Stock number:
213089
VIN:
1GCPYCEHXLZ213089

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

90,888 miles

$26,736

Great Deal
Lafayette, IN
45 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 (Satin Steel Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
90,888
Stock number:
59207B
VIN:
1GCPYCEF1LZ376471

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

82,614 miles

$27,369

Great Deal
Fort Wayne, IN
75 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray (Satin Steel Metallic)
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
82,614
Stock number:
5026P
VIN:
1GCPYCEK8NZ125611

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,839 miles

$33,972

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:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
42,839
Stock number:
VP1070A
VIN:
1GCPYCEF3MZ333171

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom 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 High Country in Winamac IN

  • Chevrolet Silverado 1500 Custom 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 Custom 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

© 2026 CarGurus, Inc., All Rights Reserved.