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 Longmeadow, MA

255 results
Longmeadow, MA
2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Lux Auto Plus

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

69,814 miles

$33,977

Good Deal
Auburn, MA
37 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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
69,814
Stock number:
LAW5855
VIN:
3GCPYFED6LG270887

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

74,933 miles

$34,777

Fair Deal
Auburn, MA
37 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:
74,933
Stock number:
LAW5831
VIN:
1GCPYFED7MZ373690

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

72,445 miles

$32,994

Great Deal
Waterbury, CT
42 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:
Mosaic Black Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
72,445
Stock number:
U9678
VIN:
1GCPYFEL3MZ350026

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

76,717 miles

$31,900

Good Deal
Avon, CT
21 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

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

68,685 miles

$34,400

Fair Deal
Shrewsbury, MA
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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
68,685
Stock number:
AU3290
VIN:
3GCPYFED9LG288705

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
19 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

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

148,636 miles

$21,895

Good Deal
Manchester, CT
20 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

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

65,376 miles

$39,745

Fair Deal
Certified Pre-Owned
Cheshire, MA
46 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:
Brown (Tan)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
White
Transmission:
Automatic
Mileage:
65,376
Stock number:
CT-6181A
VIN:
3GCUDFED3NG594543

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

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

26,538 miles

$44,924

Good Deal
North Haven, CT
46 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:
Sterling Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
26,538
Stock number:
18604MA2
VIN:
3GCUDFE86PG144052

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

72,445 miles

$32,994

Great Deal
Waterbury, CT
42 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:
Mosaic Black Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
72,445
Stock number:
U9678
VIN:
1GCPYFEL3MZ350026

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

89,975 miles

$32,994

Good Deal
Waterbury, CT
42 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:
89,975
Stock number:
U9812
VIN:
1GCPYFED4NZ108498

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

58,208 miles

$34,929

Good Deal
Waterbury, CT
42 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:
58,208
Stock number:
52033B
VIN:
1GCPYFED4MZ243057

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
20 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

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT Trail Boss
  5. / Massachusetts
  6. / Longmeadow

  • Chevrolet Silverado 1500 LT in Longmeadow MA

  • Chevrolet Silverado 1500 RST in Longmeadow MA

  • Chevrolet Silverado 1500 LTZ in Longmeadow MA

  • Chevrolet Silverado 1500 LT Trail Boss in Longmeadow MA

  • Chevrolet Silverado 1500 LT1 in Longmeadow MA

  • Chevrolet Silverado 1500 Custom in Longmeadow MA

  • Chevrolet Silverado 1500 High Country in Longmeadow MA

  • Chevrolet Silverado 1500 Custom Trail Boss in Longmeadow MA

  • Chevrolet Silverado 1500 Work Truck in Longmeadow MA

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Pittsfield MA

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in Brattleboro VT

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in Groton MA

  • Chevrolet Silverado 1500 in Albany NY

  • Chevrolet Silverado 1500 in Longmeadow MA

  • Old Chevy Trucks for Sale in Longmeadow MA

  • Classic Muscle Cars for Sale in Longmeadow MA

  • Chevrolet Trucks For Sale in Longmeadow MA

  • Cheap Muscle Cars for Sale in Longmeadow MA

  • Work Trucks for Sale in Longmeadow MA

  • Reliable Cars For Sale in Longmeadow MA

  • American Made Trucks For Sale in Longmeadow MA

  • Best Pickup Trucks For Sale in Longmeadow MA

  • Best Cars Under $5,000 For Sale in Longmeadow MA

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Longmeadow MA

  • 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

  • Richard Chevrolet

  • Sullivan's Northwest Hills Chevy Cadillac Buick GMC

  • Central Chevrolet Inc

  • Key Chevrolet

  • Balise Chevrolet GMC

  • Scranton Chevrolet of Norwich

  • Bedard Bros Auto Sales

  • Diamond Auto Group

  • O'Neills Chevrolet

  • Vachon Chevrolet

  • East Hartford Chevrolet

  • Loehmann Blasius 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.