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 Middle Island, NY

284 results
Middle Island, NY
2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Hurd Auto Mall

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

74,157 miles

$31,349

Good Deal
Johnston, RI
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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
74,157
Stock number:
JC3697A
VIN:
3GCPYFED1KG246978

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

77,056 miles

$33,942

Fair Deal
Danbury, CT
44 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:
77,056
Stock number:
X217508
VIN:
1GCPYFED0NZ217508

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

121,557 miles

$29,935

Fair Deal
Sea Girt, NJ
78 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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
121,557
Stock number:
LZ341516
VIN:
1GCPYFELXLZ341516

Sponsored

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

37,243 miles

$46,800

Good Deal
Riverhead, NY
14 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
37,243
Stock number:
UB6344
VIN:
3GCUDFEL3RG282378

2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

68,383 miles

$29,894

Great Deal
Branford, CT
29 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:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
68,383
Stock number:
P00317
VIN:
1GCPYFED4KZ398379

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

27,970 miles

$39,740

Fair Deal
Forest Hills, NY
48 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:
27,970
Stock number:
648473B
VIN:
3GCPDFEK0NG648473

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

89,007 miles

$29,199

Good Deal
Manchester, CT
65 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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic Overdrive
Mileage:
89,007
Stock number:
CT11732
VIN:
1GCPYFED0KZ402363

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

92,471 miles

$33,617

Good Deal
Old Bridge, NJ
77 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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
92,471
Stock number:
C1533F
VIN:
3GCUDFED0NG545140

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

76,717 miles

$31,900

Good Deal
Avon, CT
65 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:
Black
Transmission:
Automatic
Mileage:
76,717
Stock number:
26059A
VIN:
1GCPYFEDXLZ203855

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

425 miles

$49,500

Good Deal
New Rochelle, NY
43 mi away
Year:
2025
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:
425
Stock number:
U14856
VIN:
3GCPKFEKXSG142893

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

148,636 miles

$21,895

Good Deal
Manchester, CT
65 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:
Gideon/Very Dark Atm
Transmission:
Automatic
Mileage:
148,636
Stock number:
352116
VIN:
1GCPYFED4LZ352116

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

95,338 miles

$27,995

Great Deal
Naugatuck, CT
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:
Gray (Satin Steel Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
95,338
Stock number:
370939N
VIN:
1GCPYFED4MZ370939

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

36,230 miles

$40,999

Fair Deal
Cedar Knolls, NJ
78 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:
Jet Black
Transmission:
Automatic
Mileage:
36,230
Stock number:
B2555
VIN:
1GCPYFEL9NZ192552

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

55,037 miles

$38,995

Good Deal
Certified Pre-Owned
Freeport, NY
36 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:
Jet Black
Transmission:
Automatic
Mileage:
55,037
Stock number:
C11695
VIN:
3GCUDFED6NG649907

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

34,998 miles

$48,854

Fair Deal
Certified Pre-Owned
Norwich, CT
62 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,998
Stock number:
L9134A
VIN:
3GCUDFED8RG202713

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

32,176 miles

$38,998

Great Deal
Warwick, RI
94 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, Cloth seat trim
Transmission:
Automatic
Mileage:
32,176
Stock number:
413011BB
VIN:
1GCPYFED8NZ154495

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

19,520 miles

$40,997

Good Deal
Store transfer to Smithtown, NY
2,477 mi away • Price includes $1,999 shipping Price includes $1,999 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Blue
Interior color:
Black
Transmission:
Automatic
Mileage:
19,520
Stock number:
26433898
VIN:
1GCPYFEL0NZ228094

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

425 miles

$49,500

Good Deal
New Rochelle, NY
43 mi away
Year:
2025
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:
425
Stock number:
U14856
VIN:
3GCPKFEKXSG142893

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT Trail Boss
  5. / New York
  6. / Middle Island
  • Chevrolet Silverado 1500 LT in Middle Island NY

  • Chevrolet Silverado 1500 RST in Middle Island NY

  • Chevrolet Silverado 1500 LTZ in Middle Island NY

  • Chevrolet Silverado 1500 LT Trail Boss in Middle Island NY

  • Chevrolet Silverado 1500 LT1 in Middle Island NY

  • Chevrolet Silverado 1500 Custom in Middle Island NY

  • Chevrolet Silverado 1500 High Country in Middle Island NY

  • Chevrolet Silverado 1500 Custom Trail Boss in Middle Island NY

  • Chevrolet Silverado 1500 Work Truck in Middle Island NY

  • Chevrolet Silverado 1500 in Holtsville NY

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in Stamford CT

  • Chevrolet Silverado 1500 in New York NY

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Newburgh NY

  • Chevrolet Silverado 1500 in New Brunswick NJ

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Toms River NJ

  • Chevrolet Silverado 1500 in Middle Island NY

  • Old Chevy Trucks for Sale in Middle Island NY

  • Classic Muscle Cars for Sale in Middle Island NY

  • Chevrolet Trucks For Sale in Middle Island NY

  • Cheap Muscle Cars for Sale in Middle Island NY

  • Work Trucks for Sale in Middle Island NY

  • Reliable Cars For Sale in Middle Island NY

  • American Made Trucks For Sale in Middle Island NY

  • Best Pickup Trucks For Sale in Middle Island NY

  • Best Cars Under $5,000 For Sale in Middle Island NY

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Middle Island NY

  • 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

  • Atlantic Chevrolet Cadillac

  • Richard Chevrolet

  • LaSorsa Chevrolet

  • New Rochelle Chevrolet

  • Chevrolet of Smithtown

  • Grossman Chevrolet

  • Key Chevrolet

  • East Hills Chevrolet of Roslyn

  • Maritime Chevrolet

  • Karl Chevrolet

  • H & L Chevrolet Inc

  • Devan Chevrolet of Wilton

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.