Used 2021 Chevrolet Silverado 1500 for Sale nearWindsor, ON

How much does the 2021 Chevrolet Silverado 1500 cost?

Prices have softened 12.38% compared to this time last year, making it a favourable time to shop this model year.

There are 762 listings available, which gives you a solid amount of inventory to compare.

Is the 2021 Chevrolet Silverado 1500 a good car?

Yes — 4.6/5 is a strong user rating for the 2021 Chevrolet Silverado 1500, and the expert score is 5.5/10. The model scores 7/10 across Performance and Form and function.

Owners consistently praise the comfortable ride, spacious interior, and strong performance, and many also appreciate the power and smooth shifting of the 10-speed transmission. In use, that makes it a practical fit if you want a full-size truck that feels capable and comfortable for everyday driving. The overview also points to strong brand loyalty and continued buyer interest, which helps explain why it remains relevant in the used market.

There are still trade-offs, especially around interior quality and sound system refinement, but the truck’s broad appeal and active market presence keep it in the conversation. 31.2% of listings are priced as good or great deals, which suggests there are still worthwhile opportunities if you shop carefully.

Is the 2021 Chevrolet Silverado 1500 reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

The owner feedback points to a truck that many drivers feel they can count on, with repeated praise for its comfortable ride, spacious cabin, and strong performance. The same feedback also highlights the smooth-shifting 10-speed transmission, which supports the impression of a dependable daily-use truck.

From the expert side, the Silverado is described as fundamentally sound, but it also needs greater attention to the details. For used buyers, that means long-term ownership risk is less about the core capability and more about whether the specific truck has been maintained well and avoided the quality issues that can affect satisfaction over time.

What should I look for when buying a used 2021 Chevrolet Silverado 1500?

Key things to evaluate:

• Trim level: The Silverado comes in eight different trim levels, and the cabin quality varies enough that you should pay close attention to equipment differences. The base truck can feel sparse, while higher trims add more comfort and technology, but even the better-equipped versions still leave room for improvement in interior finish.
• Powertrain: You can find six different engines paired with 6-speed, 8-speed, and 10-speed automatic transmissions. The available Duramax turbodiesel stands out for its smooth acceleration and strong fuel efficiency, while the 6.2-litre V8 is the choice if towing strength matters most.
• Safety package: Chevrolet offers forward collision alert, pedestrian detection, automatic emergency braking, blind-spot monitoring, and rear cross-traffic alert, with Teen Driver safety technology standard and free. Adaptive cruise control, lane-departure warning, lane-keep assist, and a Safety Alert Seat are available, but stop-and-go capability and lane-centering assistance are not.
• Infotainment: The Silverado uses Chevrolet Infotainment System 3 with 7-inch and 8-inch screens. Bluetooth, Apple CarPlay, and Android Auto are standard, and the higher-end setup adds wireless Apple CarPlay and Android Auto, navigation, enhanced voice recognition, and available wireless smartphone charging.
• Fuel efficiency: The Duramax turbodiesel returned 9.6 L/100 km in combined driving during testing, against a Natural Resources Canada combined rating of 10.0 L/100 km.

Which 2021 Chevrolet Silverado 1500 trim should I buy?

The 2021 Chevrolet Silverado 1500 is offered in 8 trim levels: WT, Custom, Custom Trail Boss, LT, RST, LT Trail Boss, LTZ, High Country.

Here's the short version:

• WT: This is the work-focused starting point, and it makes sense if you want the Silverado’s core capability without paying for extra comfort or tech. It gets the basics done, but it is the trim most likely to feel stripped down.
• Custom: This trim adds a bit more everyday usability and style while staying relatively accessible. It is a sensible step up if you want a little more equipment without moving too far up the price ladder.
• Custom Trail Boss: Choose this if you want the more rugged look and off-pavement attitude that comes with the Trail Boss treatment. It suits buyers who want a tougher appearance and added capability cues.
• LT: This is the best-value choice for many shoppers because it balances equipment, comfort, and technology more effectively than the lower trims. If you want a well-rounded Silverado without stretching to luxury pricing, this is the one to focus on.
• RST: This trim leans into a more polished street-oriented appearance and gives you a more upscale feel than the lower trims. It is a good fit if style matters as much as utility.
• LT Trail Boss: This is the better pick if you want the Trail Boss character with more equipment than the lower rugged trims. It is aimed at buyers who want a more capable-feeling truck without jumping straight to luxury territory.
• LTZ: This is the trim used in the expert test truck, and it brings a more premium equipment mix, including the stronger infotainment setup and available comfort features. It is a strong choice if you want a more refined Silverado experience.
• High Country: This is the top-end trim and the one to choose if you want the most upscale version of the Silverado 1500. It is best for buyers who want maximum comfort and the most premium presentation.

The safety content also notes that Chevrolet offers a broad set of driver-assistance features, but some important upgrades remain optional rather than standard.

Is now a good time to buy a used 2021 Chevrolet Silverado 1500?

This looks like a moderate, selective buyer’s market, so you have room to shop carefully and compare listings.

• Deal availability: 31.2% of listings are priced as good or great deals.
• Inventory: There are 762 listings available.
• Price trend: Prices have softened 12.38% compared with last year.

If you find a listing below $35,439 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Chevrolet Silverado 1500's resale value?

The current average of $35,530 CAD sits slightly below last year's $40,550 CAD.

That decline suggests the market has become more favourable for buyers, but it also means future sellers may need to price more competitively to stand out. If you own one now, the softer trend can limit upside in the near term unless your truck is especially well equipped or unusually clean. On the other hand, the Silverado’s strong brand loyalty and steady shopper interest should help support demand.

Vehicles with strong owner satisfaction ratings, like this model year's 4.6/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Chevrolet Silverado 1500 safe?

The 2021 Chevrolet Silverado 1500 earns a Marginal rating for front passenger protection in an IIHS small-overlap frontal crash, and it receives an overall four-star rating from NHTSA with four-star frontal-impact results for the driver and front passenger.

It earns a 3/10 safety score from our experts.

Chevrolet includes forward collision alert, pedestrian detection, automatic emergency braking, blind-spot monitoring, rear cross-traffic alert, a rearview camera, front and rear parking sensors, automatic collision notification through connected services, and Teen Driver safety technology. Crew cabs also get a rear-seat reminder system. Available upgrades include adaptive cruise control, lane-departure warning, lane-keep assist, and a Safety Alert Seat.

The main caveat is the Silverado’s weak crash-test performance, especially the IIHS passenger result and the poor headlight rating. For used buyers, that makes it worth prioritising trucks with the safety equipment you want already installed, rather than assuming every trim delivers the same protection level.

Should I buy a 2021 Chevrolet Silverado 1500 or consider a different year?

If you're weighing the 2021 against nearby model years, here's how to think about it:

Choose the 2021 if:

• 31.2% of listings are priced as good or great deals.
• Price trend: Prices have softened 12.38% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2021 stands out for its strong brand loyalty, solid fundamentals, and available Duramax turbodiesel, even though it still needs more attention to detail.

The bottom line: If you want a used Silverado with broad availability and softer pricing, the 2021 is a reasonable place to shop. If you are price-sensitive, you may also want to compare nearby model years for the best mix of equipment and value, but the 2021 remains a sensible choice if you find a clean example with the right options.

How does the 2021 Chevrolet Silverado 1500 compare to the 2021 Ford F-150?

Our experts score the 2021 Chevrolet Silverado 1500 5.5/10 and the 2021 Ford F-150 7.8/10. The Ford comes out ahead overall, especially if you want a stronger expert-rated package and better fuel economy in the comparison data. The Silverado still has appeal if you value brand loyalty, a comfortable ride, and a lower average used price. Inventory is also more limited for the Silverado, so the Ford gives you more listings to choose from.

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from November 4, 2026, CarGurus experts' opinions, and generative AI.