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 Drayton, ON

66 results
Elmira, ON
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Mills Buick GMC

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,221 kilometres

$49,890

Fair Deal
Oshawa, ON
141 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

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,258 kilometres

$43,490

Fair Deal
Aylmer, ON
98 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:
56,258
Stock number:
P1460
VIN:
3GCPDCEK9PG195133

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab LB 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab LB 4WD

73,187 kilometres

$44,844

Good Deal
Tillsonburg, ON
84 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:
White
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
73,187
Stock number:
T25221
VIN:
3GCUDCED1PG202645

Sponsored

2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,389 kilometres

$59,998

Great Deal
Certified Pre-Owned
Thornhill, ON
95 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

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

163,252 kilometres

$31,999

Good Deal
Sarnia, ON
160 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
Transmission:
8-Speed Automatic
Mileage:
163,252
Stock number:
NG107868
VIN:
3GCPYCEKXNG107868

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
138 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

45,248 kilometres

$44,995

Good Deal
Mississauga, ON
74 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:
45,248
Stock number:
19611
VIN:
3GCPDCEK7RG237611

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
194 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

129,528 kilometres

$34,995

Good Deal
Peterborough, ON
194 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

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,535 kilometres

$43,522

Good Deal
Certified Pre-Owned
Alliston, ON
82 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

146,616 kilometres

$34,980

Good Deal
Barrie, ON
108 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

31,294 kilometres

$42,979

Good Deal
Oakville, ON
75 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:
31,294
Stock number:
348621
VIN:
3GCPDCEKXPG348621

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,820 kilometres

$51,500

Good Deal
Certified Pre-Owned
Guelph, ON
21 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:
29,820
Stock number:
P11773
VIN:
3GCUDCED6RG109638

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,979 kilometres

$49,922

Good Deal
Tillsonburg, ON
84 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:
39,979
Stock number:
T26550
VIN:
3GCUDCED9RG166089

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,742 kilometres

$43,990

Good Deal
Oakville, ON
75 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:
58,742
Stock number:
343583
VIN:
3GCUDCED8PG343583

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

74,038 kilometres

$34,995

Good Deal
London, ON
92 km away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior colour:
Black
Combined gas mileage:
14 L/100km
Fuel type:
Flex Fuel Vehicle
Interior colour:
Black
Transmission:
Automatic
Mileage:
74,038
Stock number:
3535
VIN:
1GCRYCEH3KZ312439

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,863 kilometres

$39,922

Good Deal
Certified Pre-Owned
Petrolia, ON
143 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
79,863
Stock number:
6470122
VIN:
3GCPDCED0NG667203

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,045 kilometres

$46,995

Good Deal
Kitchener, ON
17 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:
Blue
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
40,045
Stock number:
19496
VIN:
3GCUDCED1RG145964

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab LB 4WD

73,187 kilometres

$44,844

Good Deal
Tillsonburg, ON
84 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:
White
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
73,187
Stock number:
T25221
VIN:
3GCUDCED1PG202645

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

148,767 kilometres

$29,400

Good Deal
Toronto, ON
87 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

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
194 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,884 kilometres

$41,995

Fair Deal
Guelph, ON
21 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
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
101,884
Stock number:
66742
VIN:
3GCPDCED1NG587361

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

163,252 kilometres

$31,999

Good Deal
Sarnia, ON
160 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
Transmission:
8-Speed Automatic
Mileage:
163,252
Stock number:
NG107868
VIN:
3GCPYCEKXNG107868

Sponsored

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

  • Chevrolet Silverado 1500 RST in Drayton ON

  • Chevrolet Silverado 1500 LT Trail Boss in Drayton ON

  • Chevrolet Silverado 1500 Custom in Drayton ON

  • Chevrolet Silverado 1500 High Country in Drayton ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Drayton ON

  • Chevrolet Silverado 1500 LTZ in Drayton ON

  • Chevrolet Silverado 1500 Work Truck in Drayton ON

  • Chevrolet Silverado 1500 LS in Drayton ON

  • Chevrolet Silverado 1500 in Listowel ON

  • Chevrolet Silverado 1500 in Kitchener ON

  • Chevrolet Silverado 1500 in Guelph ON

  • Chevrolet Silverado 1500 in Orangeville ON

  • Chevrolet Silverado 1500 in Cambridge ON

  • Chevrolet Silverado 1500 in Milton ON

  • Chevrolet Silverado 1500 in Woodstock ON

  • Chevrolet Silverado 1500 in Brampton ON

  • Chevrolet Silverado 1500 in Brantford ON

  • Chevrolet Silverado 1500 in Drayton ON

  • Best Work Trucks for Sale in Drayton ON

  • Chevrolet Trucks For Sale in Drayton ON

  • Chevy Duramax Diesel Trucks for Sale in Drayton ON

  • Chevrolet SUVs & Crossovers for Sale in Drayton ON

  • Cheap Muscle Cars for Sale in Drayton 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 Drayton 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 Drayton

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

  • Used Hatchbacks for Sale with Low Mileage in Drayton

  • Used Convertibles for Sale with Low Mileage in Drayton

  • Used Vans for Sale with Low Mileage in Drayton

  • Used Minivans for Sale with Low Mileage in Drayton

  • Used Pickup Trucks for Sale with Low Mileage in Drayton

  • Used Coupes for Sale with Low Mileage in Drayton

  • Used Wagons for Sale with Low Mileage in Drayton

  • Wallace Chevrolet Buick Cadillac

  • Royal Chevrolet Cadillac

  • Scherer Chevrolet Buick GMC

  • Barry Cullen Chevrolet Cadillac Ltd

  • Robinson Auto Group

  • Bolton GM

  • Robinson Chevrolet

  • Gateway Chevrolet Buick GMC

  • Bennett Chevrolet Cadillac Buick GMC

  • Forbes Motors GM

  • Huron Motor Products Ltd

  • Stratford Motor Products

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.