Used 2021 Mercedes-Benz S-Class for Sale nearWinchester, VA

Compare 2021 Mercedes-Benz S-Class Trims

The S-Class offers a blend of luxury and performance, with the S 580 Sedan 4MATIC as the most accessible option in the lineup.

• Starting at $59,279
• Best MPG/MPGe: 17 city / 25 hwy
• Most Popular: S 580 Sedan 4MATIC

Trim Overview

Prices updated weekly from CarGurus listings.

Quick Compare Table

Listing prices sourced from CarGurus — updated weekly. OEM specs from manufacturer data.

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Trim Deep Dives

S 580 Sedan 4MATIC — "Who It's For"

The S 580 Sedan 4MATIC is the pick for shoppers who want luxury features without the high price of the Maybach. It's also the most popular trim in the lineup.

• Avg. market price: $59,279 (updated weekly)
• MPG/MPGe: 17 city / 25 hwy
• Inventory: 164 listings — lower availability; may limit negotiating room
• View S 580 Sedan 4MATIC listings

Maybach S 580 Sedan 4MATIC — "Who It's For"

The Maybach S 580 Sedan 4MATIC is the pick for shoppers who want the ultimate luxury experience without compromise. Its exclusivity and features justify the higher price.

• Avg. market price: $124,728 (updated weekly)
• MPG/MPGe: 16 city / 24 hwy
• Inventory: 10 listings — lower availability; may limit negotiating room
• View Maybach S 580 Sedan 4MATIC listings

Trim Recommendations

Most Popular — S 580 Sedan 4MATIC

With 164 active listings, the S 580 Sedan 4MATIC is the clear volume leader in the lineup.

Browse S 580 Sedan 4MATIC listings

Best Budget Option — S 580 Sedan 4MATIC

At $59,279 avg market price — below the lineup median of $92,003 — it's the most accessible entry point.

Browse S 580 Sedan 4MATIC listings

Best for Fuel Economy — S 580 Sedan 4MATIC

The S 580 Sedan 4MATIC leads the lineup with its fuel efficiency of 17/25 MPG.

Browse S 580 Sedan 4MATIC listings

These recommendations are based on CarGurus' proprietary market data from October 1, 2026, CarGurus experts' opinions, and generative AI.

How much does the 2021 Mercedes-Benz S-Class cost?

Prices have softened 9.86% compared to this time last year, making it a favorable time to shop this model year.

There are 748 listings available, which gives you a reasonable amount of inventory to compare.

Is the 2021 Mercedes-Benz S-Class a good car?

Generally — you’re looking at a 4/5 user-rated flagship with an expert score of 7.5/10. The model scores 9/10 across Performance and Technology.

Owners consistently praise the luxurious feel, advanced technology, and strong performance. The review summary also points to thrilling acceleration and enjoyable handling, which fits the S-Class’s role as a high-end executive sedan.

The main trade-off is the high price, and the expert review also notes that some competitors are slightly quicker. For you, that means the S-Class makes the most sense if you value comfort, tech, and prestige more than outright value or bargain performance.

Good and great deals account for 33.4% of listings, so there are still some attractive opportunities if you shop carefully.

Is the 2021 Mercedes-Benz S-Class reliable?

Owners rate it 4/5, a solid signal of long-term satisfaction.

The owner summary points to a car that feels luxurious and advanced while still delivering strong performance, and it also suggests the experience is generally positive enough that most owners are impressed. The expert review adds that the mild-hybrid setup helps with efficiency through electric assist and more aggressive stop/start behavior, which supports everyday dependability.

Mercedes also backs the car with a four-year, 50,000-mile basic warranty and a four-year, 50,000-mile powertrain warranty. Even so, the S-Class is complex enough that long-term ownership can become expensive if maintenance is neglected.

What should I look for when buying a used 2021 Mercedes-Benz S-Class?

Accident-free inventory is solid at 82% — always verify the vehicle history report.

You should still run a history report on every candidate, even if the listing looks clean. Prioritize a pre-purchase inspection that checks the tires, suspension, electronics, and driver-assistance systems, since this is a highly complex luxury sedan. Focus on overall condition and maintenance records, because the car’s sophistication can make neglected examples costly to sort out.

Key things to evaluate:

• Trim level: The S-Class comes standard with 19-inch wheels, while 20-inch and 21-inch wheels are optional. The cabin centers on the infotainment touchscreen and digital instrument cluster, and the test car’s AMG Line package added 20-inch wheels. That makes the better-equipped version the one to target if you want the full flagship feel.
• Powertrain: The S500 4Matic uses a 3.0-liter turbocharged inline-six with 429 horsepower and 384 pound-feet of torque, while the S580 4Matic uses a 4.0-liter twin-turbo V8 with 496 hp and 516 lb-ft. Both use a nine-speed automatic, EQ Boost mild-hybrid assistance, and all-wheel drive.
• Safety package: Standard driver-assistance features include adaptive cruise control with stop-and-go, automated lane centering, automatic emergency braking, forward-collision warning, blind-spot monitoring, lane-keep assist, lane-change assist, traffic-sign recognition, a driver-attention monitor, and a 360-degree camera system. The S-Class also includes an industry-first rear-passenger airbag.
• Infotainment: Standard equipment includes a 12.3-inch digital instrument cluster and a 12.8-inch OLED central touchscreen, plus wireless Apple CarPlay and Android Auto. The system also supports over-the-air-style modern connectivity through an updated MBUX setup, and available rear-seat tech adds a pair of 11.6-inch touchscreens and a 7-inch tablet.
• Fuel efficiency: The expert review says EPA fuel-economy ratings weren’t available yet, but it recorded 22.4 mpg over about 300 miles of driving.

Which 2021 Mercedes-Benz S-Class trim should I buy?

The 2021 Mercedes-Benz S-Class is offered in 2 trim levels: S500 4Matic, S580 4Matic.

Here's the short version:

• S500 4Matic: This is the better-value choice if you want the S-Class experience without paying for the V8. It still gives you the 429-horsepower inline-six, EQ Boost mild-hybrid assistance, all-wheel drive, and the same core luxury and tech foundation.
• S580 4Matic: This is the one to choose if you want the strongest performance and the most effortless flagship feel. The V8’s 496 horsepower and 516 pound-feet of torque make it the more compelling pick for buyers who want the top-end powertrain.

The standard safety package is broad, and the car’s driver-assistance systems are a major part of its appeal.

Is now a good time to buy a used 2021 Mercedes-Benz S-Class?

This is a moderate market for selective buyers, so you can shop with some leverage if you’re patient.

• Deal availability: 33.4% of listings are priced as good or great deals.
• Inventory: There are 748 listings available.
• Price trend: Prices have softened 9.86% compared with last year.
• Clean inventory: 82.0% of listings are accident-free.

If you find a listing below $58,587, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Mercedes-Benz S-Class's resale value?

The current average of $58,597 sits slightly below last year's $65,005.

That decline suggests the market has already adjusted downward, which can help you as a buyer today but may limit upside if you plan to resell soon. If you buy at the right price and keep the car in excellent condition, you’ll be better positioned to preserve value than someone who pays near the top of the range.

Vehicles with solid owner satisfaction ratings, like this model year's 4/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Mercedes-Benz S-Class safe?

The S-Class does get a plethora of safety features, including an industry-first rear-passenger airbag.

It earns a 7/10 safety score from our experts.

Standard driver-assistance features include adaptive cruise control with stop-and-go functionality, automated lane centering, automatic emergency braking, forward-collision warning, blind-spot monitoring, lane-keep assist, lane-change assist, traffic-sign recognition, a driver-attention monitor, and a 360-degree camera system. Mercedes also says traffic-sign recognition can detect stop signs and red lights, while lane-keep assist can read road edges and lets you adjust sensitivity.

Crash-test ratings from NHTSA and IIHS aren’t available, so you’ll be relying more on the car’s extensive standard safety tech than on published test results.

Should I buy a 2021 Mercedes-Benz S-Class 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:

• 33.4% of listings are priced as good or great deals.
• Accident-free inventory is solid at 82% — always verify the vehicle history report.
• Price trend: Prices have softened 9.86% compared with last year.
• Owners rate it 4/5 — a solid satisfaction signal.
• It introduces a redesigned cabin, new powertrains, and more advanced infotainment.

Consider the 2022 if:

• At $63,211, the 2022 costs more than the current year's $58,597 average.
• It keeps the same flagship formula with updated model-year pricing and a slightly newer market position.

The bottom line: If you want the better value, the 2021 is the smarter buy because prices have eased and the model already delivers the full redesign. If you’re willing to spend more for a newer model year, the 2022 is the cleaner alternative, but price-sensitive buyers should focus on the 2021’s stronger value proposition.

These recommendations are based on CarGurus' proprietary market data from September 29, 2026, CarGurus experts' opinions, and generative AI.