CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
  • Sell
    • Sell my car
    • Car values
  • Research
    • Test drive reviews
    • Price trends
    • Compare cars
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Whitby, ON

50 results
Whitby, ON
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD AutoPark Barrie

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,072 kilometres

$47,987

Good Deal
Innisfil, ON
76 km 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 colour:
Gray (Sterling Grey Metallic)
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
42,072
Stock number:
24-37977JB
VIN:
3GCUDCED6RG337977

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,753 kilometres

$51,888

Fair Deal
Mississauga, ON
72 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior colour:
Black
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
47,753
Stock number:
UM15299
VIN:
3GCUDCE8XRG215299

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,248 kilometres

$41,998

Fair Deal
St Catharines, ON
84 km 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 colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
77,248
Stock number:
E2129
VIN:
3GCPDCED5NG520097

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,613 kilometres

$39,198

Good Deal
Grimsby, ON
90 km 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 colour:
Gray
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
72,613
Stock number:
P226855
VIN:
3GCPYCEK2NG116855

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,725 kilometres

$36,688

Good Deal
Certified Pre-Owned
Woodbridge, ON
50 km 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 colour:
White
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
104,725
Stock number:
P119164
VIN:
3GCPYCEK1NG119164

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

57,396 kilometres

$42,995

Good Deal
Cobourg, ON
62 km 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 colour:
White
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
57,396
Stock number:
CK10139
VIN:
3GCPDCED3NG659189

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,072 kilometres

$47,987

Good Deal
Innisfil, ON
76 km 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 colour:
Gray (Sterling Grey Metallic)
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
42,072
Stock number:
24-37977JB
VIN:
3GCUDCED6RG337977

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,130 kilometres

$37,700

Good Deal
Mississauga, ON
60 km 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 colour:
Black
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
80,130
Stock number:
250006
VIN:
3GCPYCEK5NG183885

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,594 kilometres

$46,490

Good Deal
Cobourg, ON
60 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Gray
Interior colour:
Black
Transmission:
Automatic
Mileage:
70,594
Stock number:
RG130718
VIN:
3GCUDCEDXRG130718

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,854 kilometres

$35,888

Good Deal
Mississauga, ON
72 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
118,854
Stock number:
um00412
VIN:
3GCPYCEK9NG100412

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,541 kilometres

$47,452

Good Deal
Bolton, ON
62 km 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 colour:
Gray
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
38,541
Stock number:
U7411
VIN:
3GCPDCEK1RG237040

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,426 kilometres

$44,443

Good Deal
Bolton, ON
62 km away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior colour:
Gray
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
51,426
Stock number:
U7390
VIN:
3GCUDCED4PG332404

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,463 kilometres

$40,490

Good Deal
Cobourg, ON
60 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Red
Interior colour:
Black
Transmission:
Automatic
Mileage:
69,463
Stock number:
NG616145
VIN:
3GCPDCEDXNG616145

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

43,547 kilometres

$44,997

Good Deal
Bolton, ON
62 km away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior colour:
Black
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
43,547
Stock number:
U7378
VIN:
3GCUDCED2PG334653

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

63,110 kilometres

$39,786

Good Deal
Oakville, ON
72 km 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 colour:
Black
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
63,110
Stock number:
307318
VIN:
3GCPDCEK2PG307318

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,854 kilometres

$35,888

Good Deal
Mississauga, ON
72 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Jet Black
Transmission:
Automatic
Mileage:
118,854
Stock number:
um00412
VIN:
3GCPYCEK9NG100412

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Ontario
  6. / Whitby

  • Chevrolet Silverado 1500 LT in Whitby ON

  • Chevrolet Silverado 1500 RST in Whitby ON

  • Chevrolet Silverado 1500 LT Trail Boss in Whitby ON

  • Chevrolet Silverado 1500 Custom in Whitby ON

  • Chevrolet Silverado 1500 High Country in Whitby ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Whitby ON

  • Chevrolet Silverado 1500 LTZ in Whitby ON

  • Chevrolet Silverado 1500 Work Truck in Whitby ON

  • Chevrolet Silverado 1500 LS in Whitby ON

  • Chevrolet Silverado 1500 in Oshawa ON

  • Chevrolet Silverado 1500 in Ajax ON

  • Chevrolet Silverado 1500 in Pickering ON

  • Chevrolet Silverado 1500 in Markham ON

  • Chevrolet Silverado 1500 in Stouffville ON

  • Chevrolet Silverado 1500 in Scarborough ON

  • Chevrolet Silverado 1500 in Unionville ON

  • Chevrolet Silverado 1500 in Thornhill ON

  • Chevrolet Silverado 1500 in Richmond Hill ON

  • Chevrolet Silverado 1500 in Whitby ON

  • Best Work Trucks for Sale in Whitby ON

  • Chevrolet Trucks For Sale in Whitby ON

  • Chevy Duramax Diesel Trucks for Sale in Whitby ON

  • Chevrolet SUVs & Crossovers for Sale in Whitby ON

  • Cheap Muscle Cars for Sale in Whitby ON

  • Chevrolet Silverado 1500 in Alberta

  • Chevrolet Silverado 1500 in British Columbia

  • Chevrolet Silverado 1500 in Manitoba

  • Chevrolet Silverado 1500 in New Brunswick

  • Chevrolet Silverado 1500 in Newfoundland and Labrador

  • Chevrolet Silverado 1500 in Northwest Territories

  • Chevrolet Silverado 1500 in Nova Scotia

  • Chevrolet Silverado 1500 in Nunavut

  • Chevrolet Silverado 1500 in Ontario

  • Chevrolet Silverado 1500 in Prince Edward Island

  • Chevrolet Silverado 1500 in Quebec

  • Chevrolet Silverado 1500 in Saskatchewan

  • Chevrolet Silverado 1500 in Yukon

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Whitby ON

  • All Used Cars

  • Cheap Cars

  • Manual Transmission Cars

  • Sports Cars

  • Hybrid Cars

  • Red Interior Cars

  • Electric Cars

  • Small Cars

  • AWD Cars

  • Cheap Automatic Transmission Cars

  • Classic Trucks

  • Conversion Vans

  • Three Quarter Ton Trucks

  • Diesel Trucks

  • Small Trucks

  • Chevrolet Diesel Trucks

  • Manual Diesel Trucks

  • One Ton Trucks

  • Cheap Trucks

  • Ford Trucks

  • Cheap SUVs

  • Mercedes-Benz Convertibles

  • Ford Diesel Trucks

  • Mercedes-Benz SUVs

  • BMW Convertibles

  • Chevrolet SUVs

  • Toyota SUVs

  • Nissan SUVs

  • Used Cars Under $10,000

  • Used Cars Under $5,000

  • 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

  • Georgian Chevrolet Buick GMC

  • Roy Foss Woodbridge Chevrolet Buick GMC Cadillac

  • Nurse Chevrolet

  • Budds' Chevrolet Cadillac Buick GMC

  • Roy Foss Motors Ltd.

  • NewRoads Chevrolet Cadillac Buick GMC

  • Gateway Chevrolet Buick GMC

  • Wilson-Niblett

  • Jack McGee Peterborough

  • Boyer Chevrolet Buick GMC Ajax Ltd

  • Williamson GM Uxbridge

  • Eastside Chevrolet Buick GMC Ltd

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
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2025 CarGurus, Inc., All Rights Reserved.