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 Windsor Locks, CT

143 results
Windsor Locks, CT
2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Lux Auto Plus

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

56,240 miles

$29,977

Fair Deal
Auburn, MA
44 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:
Silver
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
56,240
Stock number:
LAW5957
VIN:
1GCRYCEF4KZ252606

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,267 miles

$24,995

Great Deal
Naugatuck, CT
34 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
81,267
Stock number:
115249N
VIN:
3GCPYCEF2KG115249

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

83,639 miles

$27,440

Fair Deal
Litchfield, CT
32 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
83,639
Stock number:
U28091
VIN:
1GCRYCEF7LZ259731

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

126,232 miles

$21,995

Fair Deal
Rochdale, MA
43 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
Transmission:
6-Speed Automatic
Mileage:
126,232
Stock number:
4432
VIN:
1GCRYCEF8KZ344432

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

81,328 miles

$26,278

Fair Deal
Willimantic, CT
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:
81,328
Stock number:
S576674A
VIN:
1GCRYCEF9KZ338722

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

83,639 miles

$27,440

Fair Deal
Litchfield, CT
32 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
83,639
Stock number:
U28091
VIN:
1GCRYCEF7LZ259731

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,410 miles

$31,444

Fair Deal
Bristol, CT
20 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:
65,410
Stock number:
UA38236A
VIN:
3GCPDCEK4NG569791

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

82,617 miles

$24,991

Good Deal
Waterbury, CT
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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
82,617
Stock number:
51977K
VIN:
1GCRYCEF6KZ422223

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,267 miles

$24,995

Great Deal
Naugatuck, CT
34 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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
81,267
Stock number:
115249N
VIN:
3GCPYCEF2KG115249

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

119,644 miles

$24,995

Good Deal
Manchester, CT
12 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:
119,644
Stock number:
224999
VIN:
3GCPYCEF7LG224999

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Connecticut
  6. / Windsor Locks

  • Chevrolet Silverado 1500 LT in Windsor Locks CT

  • Chevrolet Silverado 1500 RST in Windsor Locks CT

  • Chevrolet Silverado 1500 LTZ in Windsor Locks CT

  • Chevrolet Silverado 1500 LT Trail Boss in Windsor Locks CT

  • Chevrolet Silverado 1500 LT1 in Windsor Locks CT

  • Chevrolet Silverado 1500 High Country in Windsor Locks CT

  • Chevrolet Silverado 1500 Custom in Windsor Locks CT

  • Chevrolet Silverado 1500 Custom Trail Boss in Windsor Locks CT

  • Chevrolet Silverado 1500 Work Truck in Windsor Locks CT

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in Pittsfield MA

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in Brattleboro VT

  • Chevrolet Silverado 1500 in Groton MA

  • Chevrolet Silverado 1500 in Albany NY

  • Chevrolet Silverado 1500 in Windsor Locks CT

  • Old Chevy Trucks for Sale in Windsor Locks CT

  • Classic Muscle Cars for Sale in Windsor Locks CT

  • Chevrolet Trucks For Sale in Windsor Locks CT

  • Cheap Muscle Cars for Sale in Windsor Locks CT

  • Work Trucks for Sale in Windsor Locks CT

  • Reliable Cars For Sale in Windsor Locks CT

  • American Made Trucks For Sale in Windsor Locks CT

  • Best Pickup Trucks For Sale in Windsor Locks CT

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Windsor Locks 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

  • 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

  • Diamond Auto Group

  • Central Chevrolet Inc

  • Balise Chevrolet GMC

  • Grossman Chevrolet

  • Key Chevrolet

  • Sullivan's Northwest Hills Chevy Cadillac Buick GMC

  • O'Neills Chevrolet

  • Loehmann Blasius Chevrolet

  • Vachon Chevrolet

  • East Hartford 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.