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 Ontario

52 results
Toronto, ON
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Welland Honda

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,463 kilometres

$37,444

Fair Deal
Welland, ON
75 km 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 colour:
Black
Combined gas mileage:
16 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
101,463
Stock number:
WN25542A
VIN:
1GCPYCEF1MZ319415

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,952 kilometres

$49,995

Fair Deal
Certified Pre-Owned
Brampton, ON
28 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:
White
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
30,952
Stock number:
124795A
VIN:
3GCPDCEK9RG373500

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,000 kilometres

$50,788

Fair Deal
Guelph, ON
73 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
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
23,000
Stock number:
RG440171
VIN:
3GCUDCED6RG440171

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

43,547 kilometres

$44,443

Great Deal
Bolton, ON
35 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

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

92,109 kilometres

$29,880

Great Deal
Woodbridge, ON
23 km away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
92,109
Stock number:
290265
VIN:
1GCRYCEF7KZ290265

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,609 kilometres

$39,998

Good Deal
St Catharines, ON
57 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:
77,609
Stock number:
E2129
VIN:
3GCPDCED5NG520097

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

28,538 kilometres

$46,997

Good Deal
Bolton, ON
35 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:
Black
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
28,538
Stock number:
U7469
VIN:
3GCPDCEK8RG168881

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
30 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

26,767 kilometres

$46,798

Good Deal
Certified Pre-Owned
Thornhill, ON
17 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
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
26,767
Stock number:
TA182319
VIN:
3GCPDCEK9RG182319

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,000 kilometres

$50,788

Fair Deal
Guelph, ON
73 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
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
23,000
Stock number:
RG440171
VIN:
3GCUDCED6RG440171

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,050 kilometres

$38,888

Fair Deal
Guelph, ON
73 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:
95,050
Stock number:
NG521623
VIN:
3GCPDCEK7NG521623

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

138,616 kilometres

$36,995

Fair Deal
Cayuga, ON
89 km 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 colour:
Black
Combined gas mileage:
16 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
138,616
Stock number:
451627
VIN:
1GCPYCEF3MZ254664

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,750 kilometres

$40,488

Fair Deal
Guelph, ON
73 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:
65,750
Stock number:
NG627763
VIN:
3GCPDCEK5NG627763

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,952 kilometres

$49,995

Fair Deal
Certified Pre-Owned
Brampton, ON
28 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:
White
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
8-Speed Automatic
Mileage:
30,952
Stock number:
124795A
VIN:
3GCPDCEK9RG373500

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

228,959 kilometres

$24,999

Fair Deal
Milton, ON
42 km away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Blue
Interior colour:
Black
Transmission:
Automatic
Mileage:
228,959
Stock number:
PR6257
VIN:
1GCPYCEFXKZ280420

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

92,109 kilometres

$29,880

Great Deal
Woodbridge, ON
23 km away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
92,109
Stock number:
290265
VIN:
1GCRYCEF7KZ290265

Sponsored

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

  • Chevrolet Silverado 1500 LT in Ontario

  • Chevrolet Silverado 1500 RST in Ontario

  • Chevrolet Silverado 1500 LT Trail Boss in Ontario

  • Chevrolet Silverado 1500 Custom in Ontario

  • Chevrolet Silverado 1500 High Country in Ontario

  • Chevrolet Silverado 1500 Custom Trail Boss in Ontario

  • Chevrolet Silverado 1500 LTZ in Ontario

  • Chevrolet Silverado 1500 Work Truck in Ontario

  • Chevrolet Silverado 1500 LS in Ontario

  • Chevrolet Silverado 1500 in Toronto ON

  • Chevrolet Silverado 1500 in North York ON

  • Chevrolet Silverado 1500 in Etobicoke ON

  • Chevrolet Silverado 1500 in Thornhill ON

  • Chevrolet Silverado 1500 in Scarborough ON

  • Chevrolet Silverado 1500 in Concord ON

  • Chevrolet Silverado 1500 in Mississauga ON

  • Chevrolet Silverado 1500 in Woodbridge ON

  • Chevrolet Silverado 1500 in Vaughan ON

  • Chevrolet Silverado 1500 in Ontario

  • Best Work Trucks for Sale in Ontario

  • Chevrolet Trucks For Sale in Ontario

  • Chevy Duramax Diesel Trucks for Sale in Ontario

  • Chevrolet SUVs & Crossovers for Sale in Ontario

  • Cheap Muscle Cars for Sale in Ontario

  • 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 Ontario

  • 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

  • Wallace Chevrolet Buick Cadillac

  • Roy Foss Motors Ltd.

  • Nurse Chevrolet

  • Boyer Chevrolet Buick GMC Ajax Ltd

  • Gateway Chevrolet Buick GMC

  • Wilson-Niblett

  • Leggat Chevrolet Cadillac Buick GMC

  • Welland Chevrolet Buick GMC Inc.

  • Budds' Chevrolet Cadillac Buick GMC

  • Falls Chevrolet Cadillac Buick GMC

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

© 2026 CarGurus, Inc., All Rights Reserved.