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 2019 Chevrolet Silverado 1500 Custom Trail Boss for Sale near Middletown, VA

32 results
Middletown, VA
2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

40,976 miles

$32,450

Fair Deal
Sykesville, MD
75 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:
6-Speed Automatic Overdrive
Mileage:
40,976
Stock number:
P3530
VIN:
1GCRYCEF7KZ246699

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,558 miles

$30,995

Good Deal
Mc Connellsburg, PA
65 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:
Havana Brown Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
64,558
Stock number:
UQ242543
VIN:
1GCPYCEF1KZ242543

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

121,915 miles

$22,166

Great Deal
Woodbridge, VA
60 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
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
121,915
Stock number:
152181
VIN:
3GCPYCEF3KG152181

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,558 miles

$30,995

Good Deal
Mc Connellsburg, PA
65 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:
Havana Brown Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
64,558
Stock number:
UQ242543
VIN:
1GCPYCEF1KZ242543

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

40,976 miles

$32,450

Fair Deal
Sykesville, MD
75 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:
6-Speed Automatic Overdrive
Mileage:
40,976
Stock number:
P3530
VIN:
1GCRYCEF7KZ246699

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,613 miles

$27,995

Fair Deal
Stuarts Draft, VA
79 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:
100,613
Stock number:
5327
VIN:
3GCPYCEF4KG221833

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

86,399 miles

$25,931

Fair Deal
Glen Burnie, MD
89 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:
Red
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
86,399
Stock number:
255632A
VIN:
1GCRYCEH8KZ405733

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

94,905 miles

$25,995

Good Deal
Spotsylvania, VA
67 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
Interior color:
Black
Transmission:
Automatic
Mileage:
94,905
Stock number:
A5339
VIN:
1GCRYCEF8KZ201870

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,593 miles

$32,897

Fair Deal
Store transfer to Winchester, VA
894 mi away • Price includes $899 shipping Price includes $899 shipping
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
Interior color:
Gray
Transmission:
Automatic
Mileage:
63,593
Stock number:
27934260
VIN:
1GCPYCEF9KZ343846

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

108,561 miles

$24,995

Fair Deal
Sterling, VA
42 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
108,561
Stock number:
LB293628
VIN:
1GCRYCEFXKZ293628

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

121,915 miles

$22,166

Great Deal
Woodbridge, VA
60 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
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
121,915
Stock number:
152181
VIN:
3GCPYCEF3KG152181

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

108,561 miles

$24,995

Fair Deal
Sterling, VA
42 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
108,561
Stock number:
LB293628
VIN:
1GCRYCEFXKZ293628

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Virginia
  6. / Middletown
FAQs

Chevrolet Silverado 1500 Custom Trail Boss FAQs

How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Middletown, VA?

The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,965.64. The average price has decreased by -5% since last year. The 155 for sale near Middletown, VA on CarGurus, range from $22,222 to $56,731 in price.

How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Middletown, VA have no reported accidents or damage?

142 out of 155 for sale near Middletown, VA have no reported accidents or damage.

What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?

Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG (or MPGe).

What fuel types are available?

Diesel, Flex Fuel Vehicle, Gasoline engines are available.

  • 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

  • Country Chevrolet, Inc.

  • Lindsay Chevrolet of Front Royal

  • Michelle Radley Chevrolet

  • CMA's Chevrolet of Martinsburg and CMA's Toyota of Martinsburg

  • Battlefield 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

© 2025 CarGurus, Inc., All Rights Reserved.