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 Ajax, ON

55 results
Ajax, ON

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,023 kilometres

$43,995

Good Deal
Mississauga, ON
55 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:
48,023
Stock number:
19613
VIN:
3GCPDCEK5RG232486

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,402 kilometres

$44,490

Fair Deal
Certified Pre-Owned
Cobourg, ON
67 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:
Blue
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
21,402
Stock number:
NG661601
VIN:
3GCPDCEK6NG661601

Sponsored

2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,027 kilometres

$73,961

Fair Deal
Certified Pre-Owned
Milton, ON
77 km away
Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
3,027
Stock number:
153795
VIN:
3GCUKCED4TG153795

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

129,528 kilometres

$34,995

Great Deal
Peterborough, ON
74 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
White
Transmission:
Automatic
Mileage:
129,528
Stock number:
UT47774
VIN:
3GCPYCEK3NG147774

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

148,767 kilometres

$29,400

Great Deal
Toronto, ON
43 km 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 colour:
White
Combined gas mileage:
15 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
148,767
Stock number:
STK298537
VIN:
1GCPYCEF0KZ298537

2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,389 kilometres

$61,998

Great Deal
Certified Pre-Owned
Thornhill, ON
32 km away
Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior colour:
Green
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
3,389
Stock number:
TP193862
VIN:
3GCUKCED6TG193862

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

22,147 kilometres

$49,995

Good Deal
Peterborough, ON
74 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Gray
Transmission:
Automatic
Mileage:
22,147
Stock number:
RG130650
VIN:
3GCUDCED2RG130650

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,023 kilometres

$43,995

Good Deal
Mississauga, ON
55 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:
48,023
Stock number:
19613
VIN:
3GCPDCEK5RG232486

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

146,616 kilometres

$34,980

Good Deal
Barrie, ON
77 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:
146,616
Stock number:
G277512A
VIN:
1GCPYCEF6MZ423611

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,535 kilometres

$42,982

Good Deal
Certified Pre-Owned
Alliston, ON
78 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:
Blue
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Interior colour:
Gray
Transmission:
8-Speed Automatic
Mileage:
45,535
Stock number:
P2888
VIN:
3GCPDCEK2PG341291

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

182,000 kilometres

$26,995

Good Deal
Scarborough , ON
22 km away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
182,000
Stock number:
275670
VIN:
1GCPYCEF6LZ275670

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,221 kilometres

$48,649

Good Deal
Oshawa, ON
15 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
Automatic
Mileage:
51,221
Stock number:
U0274
VIN:
3GCUDCE82RG336036

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

227,680 kilometres

$23,999

Good Deal
Toronto, ON
46 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
Automatic
Mileage:
227,680
Stock number:
43998A
VIN:
3GCPYCEF6MG354113

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,402 kilometres

$44,490

Fair Deal
Certified Pre-Owned
Cobourg, ON
67 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:
Blue
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
21,402
Stock number:
NG661601
VIN:
3GCPDCEK6NG661601

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

57,093 kilometres

$51,664

Fair Deal
Certified Pre-Owned
Lindsay, ON
61 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
57,093
Stock number:
11-260156A
VIN:
3GCUDCED0RG411765

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,497 kilometres

$49,344

Fair Deal
Thornhill, ON
32 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:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
44,497
Stock number:
C5649
VIN:
3GCUDCED6RG135897

Preparing for a close up...

Photos coming soon

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,027 kilometres

$73,961

Fair Deal
Certified Pre-Owned
Milton, ON
77 km away
Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
3,027
Stock number:
153795
VIN:
3GCUKCED4TG153795

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,414 kilometres

$49,898

Fair Deal
Thornhill, ON
32 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:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
39,414
Stock number:
TA196323
VIN:
3GCUDCED9RG196323

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

148,767 kilometres

$29,400

Great Deal
Toronto, ON
43 km 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 colour:
White
Combined gas mileage:
15 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
148,767
Stock number:
STK298537
VIN:
1GCPYCEF0KZ298537

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Ontario
  6. / Ajax
  • Chevrolet Silverado 1500 LT in Ajax ON

  • Chevrolet Silverado 1500 RST in Ajax ON

  • Chevrolet Silverado 1500 LT Trail Boss in Ajax ON

  • Chevrolet Silverado 1500 Custom in Ajax ON

  • Chevrolet Silverado 1500 High Country in Ajax ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Ajax ON

  • Chevrolet Silverado 1500 LTZ in Ajax ON

  • Chevrolet Silverado 1500 Work Truck in Ajax ON

  • Chevrolet Silverado 1500 LS in Ajax ON

  • Chevrolet Silverado 1500 in Pickering ON

  • Chevrolet Silverado 1500 in Whitby ON

  • Chevrolet Silverado 1500 in Oshawa ON

  • Chevrolet Silverado 1500 in Markham ON

  • Chevrolet Silverado 1500 in Scarborough ON

  • Chevrolet Silverado 1500 in Unionville ON

  • Chevrolet Silverado 1500 in Stouffville ON

  • Chevrolet Silverado 1500 in Thornhill ON

  • Chevrolet Silverado 1500 in North York ON

  • Chevrolet Silverado 1500 in Ajax ON

  • Best Work Trucks for Sale in Ajax ON

  • Chevrolet Trucks For Sale in Ajax ON

  • Chevy Duramax Diesel Trucks for Sale in Ajax ON

  • Chevrolet SUVs & Crossovers for Sale in Ajax ON

  • Cheap Muscle Cars for Sale in Ajax 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 Ajax 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 in Ajax

  • Used SUVs / Crossovers for Sale with Low Mileage in Ajax

  • Used Hatchbacks for Sale with Low Mileage in Ajax

  • Used Convertibles for Sale with Low Mileage in Ajax

  • Used Vans for Sale with Low Mileage in Ajax

  • Used Minivans for Sale with Low Mileage in Ajax

  • Used Pickup Trucks for Sale with Low Mileage in Ajax

  • Used Coupes for Sale with Low Mileage in Ajax

  • Used Wagons for Sale with Low Mileage in Ajax

  • Georgian Chevrolet Buick GMC

  • Bill Spencer Chevrolet Ltd

  • Wilson-Niblett

  • Jack McGee Peterborough

  • Wallace Chevrolet Buick Cadillac

  • Roy Foss Woodbridge Chevrolet Buick GMC Cadillac

  • Brian Cullen Motors

  • Boyer Chevrolet Buick GMC Ajax Ltd

  • Williamson GM Uxbridge

  • Nurse Chevrolet

  • NewRoads Chevrolet Cadillac Buick GMC

  • Gateway Chevrolet 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.