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 Chester, NH

128 results
Chester, NH
2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Merchants Automotive Group

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,741 miles

$23,964

Good Deal
Hooksett, NH
11 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,741
Stock number:
87763
VIN:
1GCPYCEF7KZ314037

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

96,040 miles

$26,487

Fair Deal
Concord, NH
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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
96,040
Stock number:
T39309A
VIN:
1GCRYCEF8LZ239309

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

88,915 miles

$29,726

Fair Deal
Acton, MA
35 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:
8-Speed Automatic
Mileage:
88,915
Stock number:
A25720A
VIN:
3GCPDCEK7NG684420

Sponsored

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,272 miles

$33,990

Fair Deal
Malden, MA
38 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:
Northsky Blue Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
46,272
Stock number:
C15222
VIN:
1GCPYCEF5LZ352058

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,957 miles

$35,500

Fair Deal
Malden, MA
38 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:
Red Hot
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
41,957
Stock number:
C15255
VIN:
1GCPYCEF5MZ265942

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,342 miles

$29,726

Good Deal
Acton, MA
35 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
58,342
Stock number:
U3394A
VIN:
1GCPYCEF0KZ398458

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

96,040 miles

$26,487

Fair Deal
Concord, NH
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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
96,040
Stock number:
T39309A
VIN:
1GCRYCEF8LZ239309

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,704 miles

$35,429

Good Deal
Certified Pre-Owned
Dover, NH
24 mi away
Year:
2024
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
53,704
Stock number:
C54889A
VIN:
3GCPDCEK8RG103156

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

130,739 miles

$19,600

Great Deal
Peabody, MA
32 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

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,741 miles

$23,964

Good Deal
Hooksett, NH
11 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,741
Stock number:
87763
VIN:
1GCPYCEF7KZ314037

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,150 miles

$39,997

Fair Deal
Tilton, NH
37 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:
38,150
Stock number:
IC27994
VIN:
3GCUDCED3RG248660

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,495 miles

$27,377

Good Deal
Somersworth, NH
26 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:
89,495
Stock number:
20893A
VIN:
3GCPYCEF5KG229410

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,952 miles

$33,775

Good Deal
Laconia, NH
41 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:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
47,952
Stock number:
CMPT082
VIN:
1GCPYCEF1MZ278610

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,195 miles

$32,500

Great Deal
Malden, MA
38 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,342 miles

$29,726

Good Deal
Acton, MA
35 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
58,342
Stock number:
U3394A
VIN:
1GCPYCEF0KZ398458

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / New Hampshire
  6. / Chester
  • Chevrolet Silverado 1500 LT in Chester NH

  • Chevrolet Silverado 1500 RST in Chester NH

  • Chevrolet Silverado 1500 LTZ in Chester NH

  • Chevrolet Silverado 1500 LT Trail Boss in Chester NH

  • Chevrolet Silverado 1500 LT1 in Chester NH

  • Chevrolet Silverado 1500 High Country in Chester NH

  • Chevrolet Silverado 1500 Custom in Chester NH

  • Chevrolet Silverado 1500 Custom Trail Boss in Chester NH

  • Chevrolet Silverado 1500 Work Truck in Chester NH

  • Chevrolet Silverado 1500 in Manchester NH

  • Chevrolet Silverado 1500 in Portsmouth NH

  • Chevrolet Silverado 1500 in Groton MA

  • Chevrolet Silverado 1500 in Boston MA

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Brattleboro VT

  • Chevrolet Silverado 1500 in Portland ME

  • Chevrolet Silverado 1500 in Plymouth MA

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in Chester NH

  • Old Chevy Trucks for Sale in Chester NH

  • Classic Muscle Cars for Sale in Chester NH

  • Chevrolet Trucks For Sale in Chester NH

  • Cheap Muscle Cars for Sale in Chester NH

  • Work Trucks for Sale in Chester NH

  • Reliable Cars For Sale in Chester NH

  • American Made Trucks For Sale in Chester NH

  • Best Pickup Trucks For Sale in Chester NH

  • Best Cars Under $5,000 For Sale in Chester NH

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Chester NH

  • 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

  • Banks Chevrolet Buick GMC

  • Herb Connolly Chevrolet

  • Herb Chambers Chevrolet of Danvers

  • Bill Deluca Chevrolet Cadillac

  • Nucar Chevrolet of Woburn

  • Colonial West Chevrolet

  • Commonwealth Motors

  • Pride Chevrolet

  • Dover Chevrolet

  • Copeland Chevrolet Hudson

  • Colonial Chevrolet

  • McGovern Chevrolet of Arlington

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.