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 Windham, OH

317 results
Windham, OH
2025 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Victory Toyota of Ashtabula County

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

14,057 miles

$55,414

Fair Deal
Austinburg, OH
40 mi away
Year:
2025
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
14,057
Stock number:
81E11001
VIN:
3GCUKFELXSG123515

Sponsored

2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

24,366 miles

$45,800

Fair Deal
Certified Pre-Owned
Hermitage, PA
32 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Glacier Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
24,366
Stock number:
HP1170
VIN:
3GCUDFEDXPG128921

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

53,646 miles

$43,000

Fair Deal
Aurora, OH
15 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:
Sand Dune Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
53,646
Stock number:
P14962
VIN:
3GCUDFED6NG641676

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

72,653 miles

$34,988

Great Deal
Sharon, PA
31 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
72,653
Stock number:
26SF2733C
VIN:
1GCPYFEL2MZ177423

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

123,815 miles

$27,500

Great Deal
Canfield, OH
22 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:
123,815
Stock number:
250905B
VIN:
1GCPYFEL8LZ278755

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

39,419 miles

$38,801

Great Deal
North Jackson, OH
15 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:
Silver Ice Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
39,419
Stock number:
19122LT
VIN:
1GCPYFEL8MZ189558

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

50,695 miles

$37,311

Good Deal
Cleveland, OH
39 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:
Cherry Red Tintcoat
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
50,695
Stock number:
38012CY
VIN:
3GCPYFEL1MG368945

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

86,762 miles

$31,995

Good Deal
Hubbard, OH
27 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:
Black
Transmission:
Automatic
Mileage:
86,762
Stock number:
T26270A
VIN:
1GCPYFED5MZ394103

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

73,707 miles

$31,000

Great Deal
Ellwood City, PA
48 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:
Black
Transmission:
Automatic
Mileage:
73,707
Stock number:
LZ369408A
VIN:
1GCPYFED3LZ369408

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

79,379 miles

$35,000

Great Deal
Randolph, OH
16 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:
Glacier Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
79,379
Stock number:
32390A
VIN:
3GCUDFED1NG622839

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

49,500 miles

$36,900

Good Deal
Dalton, OH
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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
49,500
Stock number:
W834
VIN:
1GCPYFED6MZ224347

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

22,726 miles

$41,900

Fair Deal
Mercer, PA
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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
22,726
Stock number:
T5225M
VIN:
3GCPYFED2MG417417

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

23,426 miles

$45,490

Good Deal
Stow, OH
19 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Dark Ash Metallic
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
23,426
Stock number:
NDIC2600A
VIN:
3GCUDFE89PG262600

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

91,362 miles

$29,900

Great Deal
Alliance, OH
23 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:
91,362
Stock number:
7968A
VIN:
3GCPYFED3MG411237

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

25,552 miles

$45,950

Great Deal
Hartville, OH
23 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
25,552
Stock number:
T25246A
VIN:
3GCUDFEL4RG115589

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

84,169 miles

$32,295

Fair Deal
Burton, OH
17 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
84,169
Stock number:
260097S
VIN:
1GCPYFED2LZ202859

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT Trail Boss
  5. / Ohio
  6. / Windham
  • Chevrolet Silverado 1500 LT in Windham OH

  • Chevrolet Silverado 1500 RST in Windham OH

  • Chevrolet Silverado 1500 LTZ in Windham OH

  • Chevrolet Silverado 1500 LT Trail Boss in Windham OH

  • Chevrolet Silverado 1500 LT1 in Windham OH

  • Chevrolet Silverado 1500 Custom in Windham OH

  • Chevrolet Silverado 1500 High Country in Windham OH

  • Chevrolet Silverado 1500 Custom Trail Boss in Windham OH

  • Chevrolet Silverado 1500 Work Truck in Windham OH

  • Chevrolet Silverado 1500 in Youngstown OH

  • Chevrolet Silverado 1500 in Akron OH

  • Chevrolet Silverado 1500 in Cleveland OH

  • Chevrolet Silverado 1500 in Boyers PA

  • Chevrolet Silverado 1500 in Pittsburgh PA

  • Chevrolet Silverado 1500 in Erie PA

  • Chevrolet Silverado 1500 in Mansfield OH

  • Chevrolet Silverado 1500 in Greensburg PA

  • Chevrolet Silverado 1500 in Warren PA

  • Chevrolet Silverado 1500 in Windham OH

  • Old Chevy Trucks for Sale in Windham OH

  • Classic Muscle Cars for Sale in Windham OH

  • Chevrolet Trucks For Sale in Windham OH

  • Cheap Muscle Cars for Sale in Windham OH

  • Work Trucks for Sale in Windham OH

  • Reliable Cars For Sale in Windham OH

  • American Made Trucks For Sale in Windham OH

  • Best Pickup Trucks For Sale in Windham OH

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Windham 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

  • Huebner Chevrolet

  • Fairway Chevrolet GMC

  • Sarchione Chevrolet Randolph

  • #1 Cochran Chevrolet Buick GMC

  • Schoner Chevrolet Inc

  • McElwain Chevrolet

  • Classic Chevrolet

  • Preston Chevrolet

  • Ganley Chevrolet of Aurora

  • Tim Lally Chevrolet

  • Spitzer Chevrolet Northfield

  • Sarchione Chevrolet Garrettsville

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.