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 Portland, OH

193 results
Portland, OH
2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Toothman Ford

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,107 miles

$26,359

Great Deal
Grafton, WV
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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
80,107
Stock number:
A12564
VIN:
1GCPYCEF1KZ379837

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,659 miles

$35,913

Good Deal
Certified Pre-Owned
Johnstown, OH
93 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:
Automatic
Mileage:
35,659
Stock number:
M0615
VIN:
1GCPYCEF7MZ262668

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,228 miles

$36,851

Fair Deal
Sutton, WV
65 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:
49,228
Stock number:
14039704
VIN:
1GCPYCEL9MZ251757

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,945 miles

$36,712

Good Deal
Glen Dale, WV
86 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Dark Ash Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
25,945
Stock number:
Y924369B
VIN:
3GCPDCEK0RG112353

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

94,286 miles

$27,097

Good Deal
Canal Winchester, OH
81 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:
Blue
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
94,286
Stock number:
5649502A
VIN:
3GCPDCEK9NG573822

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,056 miles

$31,555

Great Deal
Cambridge, OH
70 mi away
Year:
2022
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
Interior color:
Gideon/Very Dark Atmosphere
Transmission:
Automatic
Mileage:
67,056
Stock number:
52133
VIN:
3GCPDCED1NG513051

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,000 miles

$28,969

Great Deal
Cambridge, OH
72 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
65,000
Stock number:
27855
VIN:
1GCPYCEK1NZ238199

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,120 miles

$30,787

Good Deal
Zanesville, OH
70 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:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,120
Stock number:
T26361A
VIN:
1GCPYCEF3MZ170814

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,647 miles

$39,088

Good Deal
Sutton, WV
65 mi away
Year:
2022
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:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
19,647
Stock number:
14039561
VIN:
3GCPDCED8NG570766

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,107 miles

$26,359

Great Deal
Grafton, WV
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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
80,107
Stock number:
A12564
VIN:
1GCPYCEF1KZ379837

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,585 miles

$32,954

Good Deal
Cambridge, OH
70 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:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
55,585
Stock number:
53105
VIN:
1GCPYCEF5MZ292851

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,647 miles

$39,088

Good Deal
Sutton, WV
65 mi away
Year:
2022
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:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
19,647
Stock number:
14039561
VIN:
3GCPDCED8NG570766

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Ohio
  6. / Portland

  • Chevrolet Silverado 1500 LT in Portland OH

  • Chevrolet Silverado 1500 RST in Portland OH

  • Chevrolet Silverado 1500 LTZ in Portland OH

  • Chevrolet Silverado 1500 LT Trail Boss in Portland OH

  • Chevrolet Silverado 1500 LT1 in Portland OH

  • Chevrolet Silverado 1500 High Country in Portland OH

  • Chevrolet Silverado 1500 Custom in Portland OH

  • Chevrolet Silverado 1500 Custom Trail Boss in Portland OH

  • Chevrolet Silverado 1500 Work Truck in Portland OH

  • Chevrolet Silverado 1500 in Parkersburg WV

  • Chevrolet Silverado 1500 in Charleston WV

  • Chevrolet Silverado 1500 in Huntington WV

  • Chevrolet Silverado 1500 in Clarksburg WV

  • Chevrolet Silverado 1500 in Newark OH

  • Chevrolet Silverado 1500 in Columbus OH

  • Chevrolet Silverado 1500 in Morgantown WV

  • Chevrolet Silverado 1500 in Mansfield OH

  • Chevrolet Silverado 1500 in Marion OH

  • Chevrolet Silverado 1500 in Portland OH

  • Old Chevy Trucks for Sale in Portland OH

  • Classic Muscle Cars for Sale in Portland OH

  • Chevrolet Trucks For Sale in Portland OH

  • Cheap Muscle Cars for Sale in Portland OH

  • Work Trucks for Sale in Portland OH

  • Reliable Cars For Sale in Portland OH

  • American Made Trucks For Sale in Portland OH

  • Best Pickup Trucks For Sale in Portland OH

  • Best Cars Under $5,000 For Sale in Portland OH

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Portland OH

  • 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

  • Mark Porter Chevrolet GMC

  • Joe Holland Chevrolet & Imports

  • Walker Chevrolet

  • Smith Chevrolet

  • Pioneer Chevrolet

  • McClinton Chevrolet & Mitsubishi

  • Joe Holland 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.