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, CT

104 results
Chester, CT
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Blasius Mitsubishi

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,749 miles

$37,581

Great Deal
Brookfield, CT
48 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
39,749
Stock number:
Z4282
VIN:
3GCUDCED1RG105755

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,227 miles

$38,000

Good Deal
Danbury, CT
49 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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
19,227
Stock number:
A207551
VIN:
3GCPDCEK8RG207551

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,403 miles

$34,198

Fair Deal
Certified Pre-Owned
New London, CT
19 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:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
56,403
Stock number:
AR83798
VIN:
1GCPYCEF4MZ283798

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

113,737 miles

$24,995

Good Deal
Windsor Locks, CT
36 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
113,737
Stock number:
275538
VIN:
3GCPYCEF6LG275538

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,757 miles

$25,999

Great Deal
Middletown, CT
14 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:
70,757
Stock number:
BM4183
VIN:
1GCPYCEF7KZ275417

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,403 miles

$34,198

Fair Deal
Certified Pre-Owned
New London, CT
19 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:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
56,403
Stock number:
AR83798
VIN:
1GCPYCEF4MZ283798

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

108,003 miles

$21,985

Good Deal
East Windsor, CT
34 mi away
Year:
2019
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:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
108,003
Stock number:
M-252424
VIN:
1GCRYCEH7KZ252424

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,286 miles

$27,995

Great Deal
Milford, CT
34 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:
95,286
Stock number:
107702
VIN:
3GCPYCELXMG107702

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,749 miles

$37,581

Great Deal
Brookfield, CT
48 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
39,749
Stock number:
Z4282
VIN:
3GCUDCED1RG105755

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

102,900 miles

$25,654

Fair Deal
Meriden, CT
18 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:
Automatic
Mileage:
102,900
Stock number:
261911
VIN:
1GCRYCEFXKZ261911

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,751 miles

$31,995

Good Deal
Selden, NY
47 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:
Automatic
Mileage:
31,751
Stock number:
10007F
VIN:
1GCPYCEF6KZ379574

Sponsored

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

  • Chevrolet Silverado 1500 RST in Chester CT

  • Chevrolet Silverado 1500 LTZ in Chester CT

  • Chevrolet Silverado 1500 LT Trail Boss in Chester CT

  • Chevrolet Silverado 1500 LT1 in Chester CT

  • Chevrolet Silverado 1500 High Country in Chester CT

  • Chevrolet Silverado 1500 Custom in Chester CT

  • Chevrolet Silverado 1500 Custom Trail Boss in Chester CT

  • Chevrolet Silverado 1500 Work Truck in Chester CT

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Holtsville NY

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in Stamford CT

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in New Bedford MA

  • Chevrolet Silverado 1500 in Newburgh NY

  • Chevrolet Silverado 1500 in Chester CT

  • Old Chevy Trucks for Sale in Chester CT

  • Classic Muscle Cars for Sale in Chester CT

  • Chevrolet Trucks For Sale in Chester CT

  • Cheap Muscle Cars for Sale in Chester CT

  • Work Trucks for Sale in Chester CT

  • Reliable Cars For Sale in Chester CT

  • American Made Trucks For Sale in Chester CT

  • Best Pickup Trucks For Sale in Chester CT

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Chester CT

  • 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 in Chester

  • Used SUVs / Crossovers for Sale with Low Mileage in Chester

  • Used Hatchbacks for Sale with Low Mileage in Chester

  • Used Convertibles for Sale with Low Mileage in Chester

  • Used Vans for Sale with Low Mileage in Chester

  • Used Minivans for Sale with Low Mileage in Chester

  • Used Pickup Trucks for Sale with Low Mileage in Chester

  • Used Coupes for Sale with Low Mileage in Chester

  • Used Wagons for Sale with Low Mileage in Chester

  • Richard Chevrolet

  • Terryville Chevrolet

  • Balise Chevrolet GMC

  • Central Chevrolet Inc

  • Sullivan's Northwest Hills Chevy Cadillac Buick GMC

  • Key Chevrolet

  • Grossman Chevrolet

  • Cargill Chevrolet

  • O'Neills Chevrolet

  • Maritime Chevrolet

  • Paul Masse Chevrolet South, Inc.

  • Vachon 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.