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 Rileyville, VA

181 results
Rileyville, VA
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Grace Auto Sales And Service

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,798 miles

$34,698

Good Deal
Richmond, VA
90 mi away
Year:
2022
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 Ice Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
65,798
Stock number:
P26067
VIN:
1GCPYCEL2NZ193007

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,679 miles

$29,500

Good Deal
Waynesboro, PA
81 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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,679
Stock number:
B34452
VIN:
1GCPYCEK9NZ119607

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,681 miles

$39,587

Fair Deal
Thurmont, MD
78 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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
27,681
Stock number:
Q260235A
VIN:
3GCPDCEK4RG194992

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,312 miles

$26,588

Good Deal
Somerset, PA
97 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:
Red Hot
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
92,312
Stock number:
S5043A
VIN:
3GCPYCEF3KG182670

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,314 miles

$25,999

Good Deal
Waynesboro, PA
81 mi away
Year:
2021
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:
Gray (Satin Steel Metallic)
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
99,314
Stock number:
U17153
VIN:
1GCPYCEH7MZ337631

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,743 miles

$32,995

Great Deal
Bedford, PA
89 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:
Blue
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
37,743
Stock number:
4512609
VIN:
3GCPDCEK4NG635708

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,453 miles

$27,300

Great Deal
Waynesboro, PA
81 mi away
Year:
2021
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
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
83,453
Stock number:
U17211
VIN:
3GCPYCEH8MG351778

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

76,679 miles

$29,500

Good Deal
Waynesboro, PA
81 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:
Shadow Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,679
Stock number:
B34452
VIN:
1GCPYCEK9NZ119607

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,320 miles

$27,500

Good Deal
Chambersburg, PA
88 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:
Summit White
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
101,320
Stock number:
26030
VIN:
1GCPYCEF4MZ323233

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,107 miles

$25,888

Great Deal
Grafton, WV
98 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:
80,107
Stock number:
A12564
VIN:
1GCPYCEF1KZ379837

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,912 miles

$29,495

Fair Deal
Frederick, MD
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:
41w
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
"black"
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,912
Stock number:
LE48390A
VIN:
1GCPYCEF1KZ242543

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,417 miles

$32,547

Great Deal
Store transfer to Winchester, VA
333 mi away • Price includes $549 shipping Price includes $549 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
50,417
Stock number:
27851520
VIN:
3GCPYCEK9NG185283

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

78,577 miles

$29,788

Good Deal
Chambersburg, PA
90 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Red Hot
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
78,577
Stock number:
WR60589A
VIN:
1GCPYCEK1NZ157574

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,470 miles

$22,995

Good Deal
Stafford, VA
56 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:
Blue
Fuel type:
Gasoline
Interior color:
Gray
Mileage:
133,470
Stock number:
DMV1729
VIN:
3GCPYCEF1MG260401

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,304 miles

$37,900

Fair Deal
Woodbridge, VA
59 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,304
Stock number:
HP9569
VIN:
3GCPDCEK3PG311751

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,746 miles

$29,981

Great Deal
Fredericksburg, VA
58 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:
83,746
Stock number:
O188447A
VIN:
3GCPYCEL6MG481465

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,050 miles

$46,488

Fair Deal
Hagerstown, MD
69 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Cypress Gray
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
8,050
Stock number:
D525085A
VIN:
3GCUKCEDXSG278833

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,107 miles

$25,888

Great Deal
Grafton, WV
98 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:
80,107
Stock number:
A12564
VIN:
1GCPYCEF1KZ379837

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Virginia
  6. / Rileyville
  • Chevrolet Silverado 1500 LT in Rileyville VA

  • Chevrolet Silverado 1500 RST in Rileyville VA

  • Chevrolet Silverado 1500 LTZ in Rileyville VA

  • Chevrolet Silverado 1500 LT Trail Boss in Rileyville VA

  • Chevrolet Silverado 1500 LT1 in Rileyville VA

  • Chevrolet Silverado 1500 Custom in Rileyville VA

  • Chevrolet Silverado 1500 High Country in Rileyville VA

  • Chevrolet Silverado 1500 Custom Trail Boss in Rileyville VA

  • Chevrolet Silverado 1500 Work Truck in Rileyville VA

  • Chevrolet Silverado 1500 in Winchester VA

  • Chevrolet Silverado 1500 in Harrisonburg VA

  • Chevrolet Silverado 1500 in Manassas VA

  • Chevrolet Silverado 1500 in Charlottesville VA

  • Chevrolet Silverado 1500 in Fredericksburg VA

  • Chevrolet Silverado 1500 in Cumberland MD

  • Chevrolet Silverado 1500 in Hagerstown MD

  • Chevrolet Silverado 1500 in Washington DC

  • Chevrolet Silverado 1500 in Richmond VA

  • Chevrolet Silverado 1500 in Rileyville VA

  • Old Chevy Trucks for Sale in Rileyville VA

  • Classic Muscle Cars for Sale in Rileyville VA

  • Chevrolet Trucks For Sale in Rileyville VA

  • Cheap Muscle Cars for Sale in Rileyville VA

  • Work Trucks for Sale in Rileyville VA

  • Reliable Cars For Sale in Rileyville VA

  • American Made Trucks For Sale in Rileyville VA

  • Best Pickup Trucks For Sale in Rileyville VA

  • Best Cars Under $5,000 For Sale in Rileyville VA

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Rileyville VA

  • 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

  • Joe Bowman Auto Plaza

  • Malloy Chevrolet Charlottesville

  • 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

© 2026 CarGurus, Inc., All Rights Reserved.