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 Keswick, ON

52 results
Keswick, ON
2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Karmann Fine Cars

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

148,767 kilometres

$29,400

Great Deal
Toronto, ON
62 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

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
90 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

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

127,927 kilometres

$34,495

Fair Deal
Richmond Hill, ON
38 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Transmission:
6-Speed Automatic
Mileage:
127,927
Stock number:
U120881
VIN:
3GCPYCEFXMG120881

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
90 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
62 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

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

22,002 kilometres

$50,995

Good Deal
Midland, ON
65 km away
Year:
2024
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:
22,002
Stock number:
00U521
VIN:
3GCUDCED3RG208823

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
90 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
66 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
22 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
35 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
55 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
61 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
58 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

57,093 kilometres

$51,664

Fair Deal
Certified Pre-Owned
Lindsay, ON
60 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
47 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
84 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

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,294 kilometres

$45,994

Fair Deal
Whitby, ON
60 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
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
31,294
Stock number:
41879X
VIN:
3GCPDCEKXPG348621

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,742 kilometres

$46,394

Fair Deal
Whitby, ON
60 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
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
58,742
Stock number:
41878X
VIN:
3GCUDCED8PG343583

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

122,043 kilometres

$38,999

Fair Deal
Certified Pre-Owned
Milton, ON
84 km away
Year:
2021
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:
122,043
Stock number:
360498A
VIN:
1GCPYCEL0MZ436800

Sponsored

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

  • Chevrolet Silverado 1500 LT in Keswick ON

  • Chevrolet Silverado 1500 RST in Keswick ON

  • Chevrolet Silverado 1500 LT Trail Boss in Keswick ON

  • Chevrolet Silverado 1500 Custom in Keswick ON

  • Chevrolet Silverado 1500 High Country in Keswick ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Keswick ON

  • Chevrolet Silverado 1500 LTZ in Keswick ON

  • Chevrolet Silverado 1500 Work Truck in Keswick ON

  • Chevrolet Silverado 1500 LS in Keswick ON

  • Chevrolet Silverado 1500 in Innisfil ON

  • Chevrolet Silverado 1500 in Newmarket ON

  • Chevrolet Silverado 1500 in Barrie ON

  • Chevrolet Silverado 1500 in Stouffville ON

  • Chevrolet Silverado 1500 in Richmond Hill ON

  • Chevrolet Silverado 1500 in Unionville ON

  • Chevrolet Silverado 1500 in Vaughan ON

  • Chevrolet Silverado 1500 in Markham ON

  • Chevrolet Silverado 1500 in Concord ON

  • Chevrolet Silverado 1500 in Keswick ON

  • Best Work Trucks for Sale in Keswick ON

  • Chevrolet Trucks For Sale in Keswick ON

  • Chevy Duramax Diesel Trucks for Sale in Keswick ON

  • Chevrolet SUVs & Crossovers for Sale in Keswick ON

  • Cheap Muscle Cars for Sale in Keswick 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 Keswick 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 Keswick

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

  • Used Hatchbacks for Sale with Low Mileage in Keswick

  • Used Convertibles for Sale with Low Mileage in Keswick

  • Used Vans for Sale with Low Mileage in Keswick

  • Used Minivans for Sale with Low Mileage in Keswick

  • Used Pickup Trucks for Sale with Low Mileage in Keswick

  • Used Coupes for Sale with Low Mileage in Keswick

  • Used Wagons for Sale with Low Mileage in Keswick

  • Georgian Chevrolet Buick GMC

  • Wilson-Niblett

  • Roy Foss Woodbridge Chevrolet Buick GMC Cadillac

  • Boyer Chevrolet Buick GMC Ajax Ltd

  • Williamson GM Uxbridge

  • Nurse Chevrolet

  • Orillia Chevrolet Buick GMC

  • Royal Chevrolet Cadillac

  • NewRoads Chevrolet Cadillac Buick GMC

  • Gateway Chevrolet Buick GMC

  • Tom Smith Chevrolet Buick GMC

  • Highland Chevrolet Buick GMC Cadillac

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.