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 Woodville, ON

103 results
Lindsay, 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

$47,900

Good Deal
Oshawa, ON
52 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

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,705 kilometres

$48,995

Fair Deal
Guelph, ON
156 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:
53,705
Stock number:
P11798
VIN:
3GCUDCED5RG314979

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,023 kilometres

$41,995

Great Deal
Mississauga, ON
108 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

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,023 kilometres

$41,995

Great Deal
Mississauga, ON
108 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

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,763 kilometres

$45,777

Great Deal
Bolton, ON
95 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:
33,763
Stock number:
U7471
VIN:
3GCUDCED3RG292254

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,759 kilometres

$39,499

Great Deal
Pickering, ON
63 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:
Silver
Combined gas mileage:
12 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
42,759
Stock number:
195379
VIN:
3GCPDCEK8PG195379

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,883 kilometres

$43,995

Great Deal
Belleville, ON
108 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
Transmission:
8-Speed Automatic
Mileage:
36,883
Stock number:
43589J
VIN:
3GCPDCEK2RG107056

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,627 kilometres

$45,998

Great Deal
Certified Pre-Owned
Thornhill, ON
82 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:
Red
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
26,627
Stock number:
TA162758
VIN:
3GCPDCEK1RG162758

Preparing for a close up...

Photos coming soon

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

974 kilometres

$59,987

Great Deal
Ajax, ON
62 km away
Year:
2026
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:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
974
Stock number:
18-B10184
VIN:
3GCPKCEK1TG249265

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,101 kilometres

$47,980

Great Deal
Belleville, ON
108 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
Transmission:
Automatic
Mileage:
37,101
Stock number:
R26110
VIN:
3GCUDCE85RG242474

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,719 kilometres

$50,500

Good Deal
Midland, ON
99 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:
26,719
Stock number:
00U35
VIN:
3GCUDCED2RG411931

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,342 kilometres

$49,900

Good Deal
Midland, ON
99 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:
29,342
Stock number:
00U536
VIN:
3GCUDCED4RG201427

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,107 kilometres

$49,900

Good Deal
Midland, ON
99 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:
24,107
Stock number:
00U528
VIN:
3GCUDCED4RG215554

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,543 kilometres

$42,488

Good Deal
Guelph, ON
156 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:
Red
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
49,543
Stock number:
25-409X
VIN:
3GCPYCEL8NG106081

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,227 kilometres

$44,995

Good Deal
Mississauga, ON
108 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:
33,227
Stock number:
19996
VIN:
3GCPDCEKXRG294997

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,945 kilometres

$45,995

Good Deal
Mississauga, ON
108 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:
37,945
Stock number:
19883
VIN:
3GCUDCED6RG107050

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,879 kilometres

$45,998

Good Deal
New Hamburg, ON
191 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:
38,879
Stock number:
924970
VIN:
3GCPDCEK2RG241730

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,936 kilometres

$46,995

Good Deal
Kitchener, ON
168 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:
41,936
Stock number:
19882
VIN:
3GCUDCED0RG131750

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,454 kilometres

$48,998

Good Deal
Certified Pre-Owned
Thornhill, ON
82 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:
Red
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
32,454
Stock number:
TA367876
VIN:
3GCUDCED7RG367876

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,043 kilometres

$47,998

Good Deal
Certified Pre-Owned
Thornhill, ON
82 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:
40,043
Stock number:
TA196323
VIN:
3GCUDCED9RG196323

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

228,959 kilometres

$23,999

Good Deal
Milton, ON
130 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

111,000 kilometres

$42,990

Good Deal
103 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:
111,000
Stock number:
103250
VIN:
3GCUDCED6RG193038

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,201 kilometres

$48,770

Good Deal
London, ON
247 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:
White
Fuel type:
Diesel
Transmission:
8-Speed Automatic
Mileage:
50,201
Stock number:
15-U1289
VIN:
3GCUDCE89RG241120

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,543 kilometres

$42,488

Good Deal
Guelph, ON
156 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:
Red
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
49,543
Stock number:
25-409X
VIN:
3GCPYCEL8NG106081

Sponsored

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

  • Chevrolet Silverado 1500 RST in Woodville ON

  • Chevrolet Silverado 1500 LT Trail Boss in Woodville ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Woodville ON

  • Chevrolet Silverado 1500 Custom in Woodville ON

  • Chevrolet Silverado 1500 High Country in Woodville ON

  • Chevrolet Silverado 1500 LTZ in Woodville ON

  • Chevrolet Silverado 1500 Work Truck in Woodville ON

  • Chevrolet Silverado 1500 LS in Woodville ON

  • Chevrolet Silverado 1500 in Innisfil ON

  • Chevrolet Silverado 1500 in Stouffville ON

  • Chevrolet Silverado 1500 in Newmarket ON

  • Chevrolet Silverado 1500 in Peterborough ON

  • Chevrolet Silverado 1500 in Barrie ON

  • Chevrolet Silverado 1500 in Oshawa ON

  • Chevrolet Silverado 1500 in Whitby ON

  • Chevrolet Silverado 1500 in Ajax ON

  • Chevrolet Silverado 1500 in Markham ON

  • Chevrolet Silverado 1500 in Woodville ON

  • Best Work Trucks for Sale in Woodville ON

  • Chevrolet Trucks For Sale in Woodville ON

  • Chevy Duramax Diesel Trucks for Sale in Woodville ON

  • Chevrolet SUVs & Crossovers for Sale in Woodville ON

  • Cheap Muscle Cars for Sale in Woodville 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 Woodville 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 Woodville

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

  • Used Hatchbacks for Sale with Low Mileage in Woodville

  • Used Convertibles for Sale with Low Mileage in Woodville

  • Used Vans for Sale with Low Mileage in Woodville

  • Used Minivans for Sale with Low Mileage in Woodville

  • Used Pickup Trucks for Sale with Low Mileage in Woodville

  • Used Coupes for Sale with Low Mileage in Woodville

  • Used Wagons for Sale with Low Mileage in Woodville

  • Georgian Chevrolet Buick GMC

  • Wilson-Niblett

  • Bill Spencer Chevrolet Ltd

  • Jack McGee Peterborough

  • Orillia Chevrolet Buick GMC

  • Boyer Chevrolet Buick GMC Ajax Ltd

  • NewRoads Chevrolet Cadillac Buick GMC

  • Nurse Chevrolet

  • Highland Chevrolet Buick GMC Cadillac

  • Tom Smith Chevrolet Buick GMC

  • Williamson GM Uxbridge

  • Roy Nichols Motors Chevrolet

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.