Used 2021 Chevrolet Silverado 2500HD for Sale nearOakville, ON

Summary

• With 20 currently listed for sale near Oakville, ON and an average price of $44,199.00 CAD, 45.0% of 2021 Chevrolet Silverado 2500HDs for sale on CarGurus are rated as good or great deals.

• Favourably reviewed: Owners rated the 2021 Chevrolet Silverado 2500HD 4.67 / 5 stars.

• 100.0% of 2021 Silverado 2500HD models on CarGurus are accident free.

Why it stands out

The 2021 Chevrolet Silverado 2500HD stands out as a heavy-duty truck that blends serious capability with a more modern, feature-rich cabin than older work-focused pickups. It is part of the redesigned fourth generation, which brought much more aggressive styling, a fully boxed frame made from seven different types of steel, and a structure Chevrolet says is 20% stiffer than before. It also offers substantial towing strength, with the most extreme configuration able to tow 9,000 kilograms with a regular hitch or 10,000 kilograms with a Gooseneck, while many other versions still manage at least 6,500 kilograms.

What makes this truck especially appealing is how much equipment Chevrolet built into even the Work Truck trim. Standard features include a 7-inch touchscreen, Bluetooth connectivity, Apple CarPlay, Android Auto, a subscription-based Wi-Fi hotspot, and a 3.5-inch digital instrument display. The 2021 Silverado 2500HD also benefits from a wide range of driver and trailering assistance features, including blind spot monitoring with rear cross-traffic alerts, park assist, and adaptive cruise control with trailer monitoring. Buyers also get a choice of cab and bed configurations, plus gas or diesel V8 power, with the standard 6.6-litre gas engine making 401 horsepower and 464 pound-feet of torque and the optional 6.6-litre Duramax turbodiesel producing 445 horsepower and 910 pound-feet of torque.

There are trade-offs, though. The truck’s bold styling comes with reduced visibility in tight spaces, and its size can limit trail use. Some versions also lag on payload, and the cabin, while improved, can still feel less polished than some rivals. Even so, the 2021 Silverado 2500HD remains a compelling choice for buyers who want a highly capable heavy-duty pickup with strong towing numbers, broad configuration choices, and a long list of useful technology.

Other model years to consider

• 2025 Chevrolet Silverado 2500HD

  • Average price: $67,430.00 CAD
  • Good/great deal percentage: 35.4%
  • User rating: 5 / 5
  • Total listings: 48

• 2023 Chevrolet Silverado 2500HD

  • Average price: $60,528.00 CAD
  • Good/great deal percentage: 36.2%
  • User rating: 4.75 / 5
  • Total listings: 47

• 2022 Chevrolet Silverado 2500HD

  • Average price: $48,214.00 CAD
  • Good/great deal percentage: 37.5%
  • User rating: 4.8 / 5
  • Total listings: 32

This analysis is based on CarGurus' proprietary market data from September 2, 2026, CarGurus experts' opinions, and generative AI.