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 Middlefield, CT

149 results
Middlefield, CT
2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD AutoLand USA

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

111,126 miles

$19,995

Great Deal
Selden, NY
48 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:
Jet Black
Transmission:
Automatic
Mileage:
111,126
Stock number:
9718F
VIN:
1GCRYCEF4KZ298680

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,832 miles

$30,990

Good Deal
Riverhead, NY
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:
Black
Transmission:
Automatic
Mileage:
53,832
Stock number:
U22935
VIN:
1GCPYCEF7MZ418546

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,702 miles

$34,945

Fair Deal
Danbury, CT
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:
Dark Ash Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
35,702
Stock number:
A686790
VIN:
3GCPDCEK6NG686790

Sponsored

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

81,328 miles

$26,278

Fair Deal
Willimantic, CT
28 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,832 miles

$30,990

Good Deal
Riverhead, NY
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:
Black
Transmission:
Automatic
Mileage:
53,832
Stock number:
U22935
VIN:
1GCPYCEF7MZ418546

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
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:
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 Crew Cab 4WD

83,810 miles

$26,602

Good Deal
Stratford, CT
31 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:
83,810
Stock number:
109712
VIN:
3GCPYCEF8KG175553

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,149 miles

$34,997

Fair Deal
Store transfer to Waterbury, CT
2,592 mi away • Price includes $1,999 shipping Price includes $1,999 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Blue
Interior color:
Black
Transmission:
Automatic
Mileage:
50,149
Stock number:
28196708
VIN:
3GCPYCEK9NG178463

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

95,094 miles

$22,902

Great Deal
Watertown, CT
20 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:
95,094
Stock number:
T3813A
VIN:
1GCRYCEF6KZ340315

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,251 miles

$35,195

Good Deal
Pawling, NY
45 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:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,251
Stock number:
A605415
VIN:
3GCPDCEK4NG605415

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,267 miles

$24,853

Great Deal
Naugatuck, CT
16 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

81,932 miles

$26,999

Good Deal
Certified Pre-Owned
Hamden, CT
14 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
81,932
Stock number:
C25355A
VIN:
3GCPYCEH9LG226500

Sponsored

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

  • Chevrolet Silverado 1500 RST in Middlefield CT

  • Chevrolet Silverado 1500 LTZ in Middlefield CT

  • Chevrolet Silverado 1500 LT Trail Boss in Middlefield CT

  • Chevrolet Silverado 1500 LT1 in Middlefield CT

  • Chevrolet Silverado 1500 High Country in Middlefield CT

  • Chevrolet Silverado 1500 Custom in Middlefield CT

  • Chevrolet Silverado 1500 Custom Trail Boss in Middlefield CT

  • Chevrolet Silverado 1500 Work Truck in Middlefield CT

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Holtsville NY

  • Chevrolet Silverado 1500 in Stamford CT

  • Chevrolet Silverado 1500 in Newburgh NY

  • Chevrolet Silverado 1500 in Providence RI

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Pittsfield MA

  • Chevrolet Silverado 1500 in Middlefield CT

  • Old Chevy Trucks for Sale in Middlefield CT

  • Classic Muscle Cars for Sale in Middlefield CT

  • Chevrolet Trucks For Sale in Middlefield CT

  • Cheap Muscle Cars for Sale in Middlefield CT

  • Work Trucks for Sale in Middlefield CT

  • Reliable Cars For Sale in Middlefield CT

  • American Made Trucks For Sale in Middlefield CT

  • Best Pickup Trucks For Sale in Middlefield CT

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Middlefield 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

  • Ingersoll Auto of Pawling

  • Balise Chevrolet GMC

  • Central Chevrolet Inc

  • Grossman Chevrolet

  • Key Chevrolet

  • Sullivan's Northwest Hills Chevy Cadillac Buick GMC

  • Karl Chevrolet

  • Maritime Chevrolet

  • O'Neills Chevrolet

  • Eagle Chevrolet of Riverhead

  • 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.