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 High Country for Sale near Windsor, ON

29 results
Windsor, ON
2026 Chevrolet Silverado 1500 High Country Crew Cab 4WD Robinson Chevrolet Buick GMC Simcoe

2026 Chevrolet Silverado 1500

High Country Crew Cab 4WD

3,000 kilometres

$79,999

Great Deal
Certified Pre-Owned
Simcoe, ON
231 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:
Black
Combined gas mileage:
15 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
3,000
Stock number:
26T5
VIN:
2GCUKJED2T1100865

Sponsored

2025 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2025 Chevrolet Silverado 1500

High Country Crew Cab 4WD

12,599 kilometres

$73,800

Fair Deal
Kitchener, ON
249 km away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
JET BLACK, PERFORATED LEATHER SEATING SURFACES
Transmission:
Automatic
Mileage:
12,599
Stock number:
51756C
VIN:
1GCUKJE80SZ316948

Sponsored

2022 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

63,667 kilometres

$53,995

Fair Deal
Chatham, ON
69 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
Transmission:
Automatic
Mileage:
63,667
Stock number:
CC00251Z
VIN:
3GCUDJED1NG506124

Sponsored

2026 Chevrolet Silverado 1500 High Country Crew Cab 4WD

2026 Chevrolet Silverado 1500

High Country Crew Cab 4WD

3,000 kilometres

$79,999

Great Deal
Certified Pre-Owned
Simcoe, ON
231 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:
Black
Combined gas mileage:
15 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
3,000
Stock number:
26T5
VIN:
2GCUKJED2T1100865

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

39,745 kilometres

$57,995

Great Deal
Chatham, ON
69 km away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Gray
Transmission:
Automatic
Mileage:
39,745
Stock number:
CC00225Z
VIN:
3GCUDJEL9PG326951

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

High Country Crew Cab 4WD

99,651 kilometres

$45,194

Great Deal
Certified Pre-Owned
London, ON
172 km away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior colour:
Black
Combined gas mileage:
9 L/100km
Fuel type:
Diesel
Interior colour:
Black
Transmission:
Automatic
Mileage:
99,651
Stock number:
265068C
VIN:
1GCUYHETXLZ362543

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

98,951 kilometres

$47,990

Great Deal
Certified Pre-Owned
Tillsonburg, ON
213 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior colour:
Black
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Interior colour:
Black
Transmission:
Automatic
Mileage:
98,951
Stock number:
26G97A
VIN:
1GCUYHET2NZ184078

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

High Country Crew Cab 4WD

47,574 kilometres

$63,995

Good Deal
Listowel, ON
232 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
Interior colour:
Black
Transmission:
Automatic
Mileage:
47,574
Stock number:
284628
VIN:
3GCUDJE81RG284628

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

High Country Crew Cab 4WD

35,750 kilometres

$72,284

Good Deal
Certified Pre-Owned
Exeter, ON
170 km away
Year:
2025
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:
35,750
Stock number:
107020
VIN:
3GCUKJE82SG307264

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

High Country Crew Cab 4WD

81,242 kilometres

$47,194

Good Deal
Certified Pre-Owned
London, ON
172 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
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Interior colour:
Black
Transmission:
Automatic
Mileage:
81,242
Stock number:
265039B
VIN:
1GCUYHED7MZ109822

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

High Country Crew Cab 4WD

63,667 kilometres

$53,995

Fair Deal
Chatham, ON
69 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
Transmission:
Automatic
Mileage:
63,667
Stock number:
CC00251Z
VIN:
3GCUDJED1NG506124

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

High Country Crew Cab 4WD

28,606 kilometres

$71,340

Fair Deal
Certified Pre-Owned
Tillsonburg, ON
213 km away
Year:
2025
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
Interior colour:
Black
Transmission:
Automatic
Mileage:
28,606
Stock number:
U-3036
VIN:
2GCUKJED9S1150046

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

High Country Crew Cab 4WD

12,599 kilometres

$73,800

Fair Deal
Kitchener, ON
249 km away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
JET BLACK, PERFORATED LEATHER SEATING SURFACES
Transmission:
Automatic
Mileage:
12,599
Stock number:
51756C
VIN:
1GCUKJE80SZ316948

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

High Country Crew Cab 4WD

28,606 kilometres

$71,340

Fair Deal
Certified Pre-Owned
Tillsonburg, ON
213 km away
Year:
2025
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
Interior colour:
Black
Transmission:
Automatic
Mileage:
28,606
Stock number:
U-3036
VIN:
2GCUKJED9S1150046

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / High Country
  5. / Ontario
  6. / Windsor

  • Chevrolet Silverado 1500 LT in Windsor ON

  • Chevrolet Silverado 1500 RST in Windsor ON

  • Chevrolet Silverado 1500 LT Trail Boss in Windsor ON

  • Chevrolet Silverado 1500 Custom in Windsor ON

  • Chevrolet Silverado 1500 High Country in Windsor ON

  • Chevrolet Silverado 1500 Custom Trail Boss in Windsor ON

  • Chevrolet Silverado 1500 LTZ in Windsor ON

  • Chevrolet Silverado 1500 Work Truck in Windsor ON

  • Chevrolet Silverado 1500 LS in Windsor ON

  • Chevrolet Silverado 1500 in Sarnia ON

  • Chevrolet Silverado 1500 in London ON

  • Chevrolet Silverado 1500 in Woodstock ON

  • Chevrolet Silverado 1500 in Listowel ON

  • Chevrolet Silverado 1500 in Kitchener ON

  • Chevrolet Silverado 1500 in Brantford ON

  • Chevrolet Silverado 1500 in Cambridge ON

  • Chevrolet Silverado 1500 in Selkirk ON

  • Chevrolet Silverado 1500 in Guelph ON

  • Chevrolet Silverado 1500 in Windsor ON

  • Best Work Trucks for Sale in Windsor ON

  • Chevrolet Trucks For Sale in Windsor ON

  • Chevy Duramax Diesel Trucks for Sale in Windsor ON

  • Chevrolet SUVs & Crossovers for Sale in Windsor ON

  • Cheap Muscle Cars for Sale in Windsor 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 High Country in Windsor ON

  • 2018 Chevrolet Silverado 1500 High Country in Windsor ON

  • 2017 Chevrolet Silverado 1500 High Country in Windsor ON

  • 2016 Chevrolet Silverado 1500 High Country in Windsor ON

  • 2015 Chevrolet Silverado 1500 High Country in Windsor ON

  • 2014 Chevrolet Silverado 1500 High Country in Windsor 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 Windsor

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

  • Used Hatchbacks for Sale with Low Mileage in Windsor

  • Used Convertibles for Sale with Low Mileage in Windsor

  • Used Vans for Sale with Low Mileage in Windsor

  • Used Minivans for Sale with Low Mileage in Windsor

  • Used Pickup Trucks for Sale with Low Mileage in Windsor

  • Used Coupes for Sale with Low Mileage in Windsor

  • Used Wagons for Sale with Low Mileage in Windsor

  • Premier Chevrolet Buick GMC Cadillac

  • Lally 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.