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 Willoughby, OH

158 results
Willoughby, OH
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Tim Lally Chevrolet

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,934 miles

$29,800

Fair Deal
Warrensville HTS, OH
16 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,934
Stock number:
T260050A
VIN:
1GCPYCEH6MZ198866

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,772 miles

$26,505

Good Deal
Westlake, OH
28 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:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
80,772
Stock number:
14945T
VIN:
1GCPYCEF4KZ349523

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,390 miles

$27,595

Fair Deal
Beachwood, OH
13 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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
92,390
Stock number:
T114539A
VIN:
3GCPYCEF6LG185421

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

91,322 miles

$26,500

Great Deal
Randolph, OH
43 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:
91,322
Stock number:
31592A
VIN:
1GCPYCEF7MZ450123

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

82,958 miles

$26,985

Good Deal
Medina, OH
41 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
82,958
Stock number:
G260187A
VIN:
1GCPYCEH3MZ372411

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,312 miles

$29,995

Good Deal
Newton Falls, OH
38 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:
Black
Transmission:
Automatic
Mileage:
79,312
Stock number:
25239A
VIN:
1GCPYCEL3NZ106392

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,668 miles

$36,500

Fair Deal
Randolph, OH
43 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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
45,668
Stock number:
32307A
VIN:
3GCPDCEK5PG298498

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,500 miles

$31,998

Great Deal
Stow, OH
33 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:
Black
Transmission:
8-Speed Automatic
Mileage:
32,500
Stock number:
NLDC6278A
VIN:
3GCPYCEK1NG183026

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,453 miles

$28,980

Great Deal
North Royalton, OH
29 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:
Blue
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
48,453
Stock number:
A332
VIN:
1GCPYCEH3LZ272226

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,059 miles

$31,900

Good Deal
Mentor, OH
4 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:
Silver Ice Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gideon/Very Dark Atmosphere
Transmission:
6-Speed Automatic Overdrive
Mileage:
41,059
Stock number:
18754T
VIN:
3GCPYCEF6KG132586

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,934 miles

$29,800

Fair Deal
Warrensville HTS, OH
16 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,934
Stock number:
T260050A
VIN:
1GCPYCEH6MZ198866

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

83,447 miles

$25,700

Fair Deal
North Olmsted, OH
31 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
83,447
Stock number:
TZ267481
VIN:
1GCRYCEF8KZ267481

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

97,076 miles

$23,979

Fair Deal
Westlake, OH
28 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
97,076
Stock number:
14728T
VIN:
1GCRYCEF9KZ323492

Sponsored

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

  • Chevrolet Silverado 1500 LT in Willoughby OH

  • Chevrolet Silverado 1500 RST in Willoughby OH

  • Chevrolet Silverado 1500 LTZ in Willoughby OH

  • Chevrolet Silverado 1500 LT Trail Boss in Willoughby OH

  • Chevrolet Silverado 1500 LT1 in Willoughby OH

  • Chevrolet Silverado 1500 Custom in Willoughby OH

  • Chevrolet Silverado 1500 High Country in Willoughby OH

  • Chevrolet Silverado 1500 Custom Trail Boss in Willoughby OH

  • Chevrolet Silverado 1500 Work Truck in Willoughby OH

  • Chevrolet Silverado 1500 in Cleveland OH

  • Chevrolet Silverado 1500 in Akron OH

  • Chevrolet Silverado 1500 in Youngstown OH

  • Chevrolet Silverado 1500 in Erie PA

  • Chevrolet Silverado 1500 in Mansfield OH

  • Chevrolet Silverado 1500 in Boyers PA

  • Chevrolet Silverado 1500 in Detroit MI

  • Chevrolet Silverado 1500 in Pittsburgh PA

  • Chevrolet Silverado 1500 in Toledo OH

  • Chevrolet Silverado 1500 in Willoughby OH

  • Old Chevy Trucks for Sale in Willoughby OH

  • Classic Muscle Cars for Sale in Willoughby OH

  • Chevrolet Trucks For Sale in Willoughby OH

  • Cheap Muscle Cars for Sale in Willoughby OH

  • Work Trucks for Sale in Willoughby OH

  • Reliable Cars For Sale in Willoughby OH

  • American Made Trucks For Sale in Willoughby OH

  • Best Pickup Trucks For Sale in Willoughby OH

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Willoughby 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

  • Sarchione Chevrolet Randolph

  • Schoner Chevrolet Inc

  • Classic Chevrolet

  • Preston Chevrolet

  • Ganley Chevrolet of Aurora

  • Tim Lally Chevrolet

  • Spitzer Chevrolet Northfield

  • Spitzer Chevrolet Amherst

  • Sarchione Chevrolet Garrettsville

  • Classic Chrysler Dodge Jeep Ram

  • Classic Chevrolet GMC of Madison

  • Spitzer Auto World Lordstown

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.