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 Rockland, MA

130 results
Rockland, MA
2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Auto Factory

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

130,739 miles

$21,800

Fair Deal
Peabody, MA
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:
White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
130,739
Stock number:
404764
VIN:
1GCRYCEF5KZ404764

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,700 miles

$35,924

Fair Deal
Raynham, MA
16 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:
Dark Ash Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
37,700
Stock number:
B8019
VIN:
3GCPDCEK8NG576517

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

78,844 miles

$27,700

Great Deal
Westborough, MA
39 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
78,844
Stock number:
T78329B
VIN:
3GCPYCEF8LG442157

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

78,844 miles

$27,700

Great Deal
Westborough, MA
39 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
78,844
Stock number:
T78329B
VIN:
3GCPYCEF8LG442157

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,195 miles

$31,990

Great Deal
Malden, MA
23 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
44,195
Stock number:
C14811
VIN:
3GCPYCEK3NG116041

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,144 miles

$40,300

Fair Deal
Norwood, MA
15 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
38,144
Stock number:
U2400050
VIN:
3GCUDCED3RG248660

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,842 miles

$33,768

Great Deal
Certified Pre-Owned
East Greenwich, RI
46 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
45,842
Stock number:
Y751A
VIN:
1GCPYCEF6MZ261981

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

96,582 miles

$29,200

Fair Deal
Johnston, RI
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:
Silver Ice Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
96,582
Stock number:
H66001B
VIN:
1GCPYCEF0MZ266979

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,635 miles

$46,924

Fair Deal
Raynham, MA
16 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Cypress Gray
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
1,635
Stock number:
M0131A
VIN:
3GCUKCED8SG339385

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,331 miles

$29,758

Fair Deal
Lynn, MA
22 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,331
Stock number:
PC2507
VIN:
1GCPYCEH3LZ189704

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,822 miles

$34,500

Good Deal
Raynham, MA
15 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:
Silver Ice Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
41,822
Stock number:
N50367B
VIN:
1GCPYCEF0MZ420087

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

102,103 miles

$24,500

Good Deal
Framingham, MA
30 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
102,103
Stock number:
C34140A
VIN:
1GCRYCEF1KZ246584

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Massachusetts
  6. / Rockland
  • Chevrolet Silverado 1500 LT in Rockland MA

  • Chevrolet Silverado 1500 RST in Rockland MA

  • Chevrolet Silverado 1500 LTZ in Rockland MA

  • Chevrolet Silverado 1500 LT Trail Boss in Rockland MA

  • Chevrolet Silverado 1500 LT1 in Rockland MA

  • Chevrolet Silverado 1500 Custom in Rockland MA

  • Chevrolet Silverado 1500 High Country in Rockland MA

  • Chevrolet Silverado 1500 Custom Trail Boss in Rockland MA

  • Chevrolet Silverado 1500 Work Truck in Rockland MA

  • Chevrolet Silverado 1500 in Plymouth MA

  • Chevrolet Silverado 1500 in Boston MA

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in New Bedford MA

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Groton MA

  • Chevrolet Silverado 1500 in Portsmouth NH

  • Chevrolet Silverado 1500 in Manchester NH

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Rockland MA

  • Old Chevy Trucks for Sale in Rockland MA

  • Classic Muscle Cars for Sale in Rockland MA

  • Chevrolet Trucks For Sale in Rockland MA

  • Cheap Muscle Cars for Sale in Rockland MA

  • Work Trucks for Sale in Rockland MA

  • Reliable Cars For Sale in Rockland MA

  • American Made Trucks For Sale in Rockland MA

  • Best Pickup Trucks For Sale in Rockland MA

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Rockland 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

  • Herb Connolly Chevrolet

  • Hurd Auto Mall

  • Nucar Chevrolet of Woburn

  • Bill Deluca Chevrolet Cadillac

  • Herb Chambers Chevrolet of Danvers

  • Copeland Chevrolet

  • Commonwealth Motors

  • Copeland Chevrolet Hudson

  • Pride Chevrolet

  • Colonial Chevrolet

  • Copeland Chevrolet Hyannis

  • Diamond Auto Group

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.