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491 listings
- Price Drop
- 59,893 miles
- No accidents, 1 owner, personal use
- 20 City / 29 Hwy MPG
- Universal Auto Group (163 mi away)
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Located in Silver Spring, MD / 163 miles away from Chesapeake, VA
An icon of exclusive luxury, our One Owner 2021 Mercedes-Benz S 500 4MATIC® Sedan with the Warmth and Comfort Pack exudes elegance and innovation in b...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: W1K6G6DB1MA032983
Stock: 17714
Certified Pre-Owned: No
Listed since: 06-30-2025 - New Listing
- 16,083 miles
- 16 City / 25 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
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Located in Tampa, FL / 699 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GB9PA167358
Stock: 27762063
Certified Pre-Owned: No - $154,881great price$20,816 below market
- 23,878 miles
- No accidents, 1 owner, personal use only
- Euro Motorcars Bethesda (162 mi away)
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Located in Bethesda, MD / 162 miles away from Chesapeake, VA
Clean CARFAX. Certified. 9-Speed Automatic 4.0L V8, 4MATIC , Black Leather, 4-Zone Climate Control, Active Multicontour Rear Seats, Adaptive Rear Ligh...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: W1K6G8CB0RA297804
Stock: MB251259A
Certified Pre-Owned: Yes
Listed since: 05-09-2025 - $33,850great price$4,585 below market
- 58,448 miles
- 1 accident, 1 owner, rental vehicle
- 19 City / 28 Hwy MPG
- District Auto Group (150 mi away)
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Located in Temple Hills, MD / 150 miles away from Chesapeake, VA
CARFAX One-Owner. Black Leather, ABS brakes, Adaptive suspension, Alloy wheels, Android Auto®, Apple CarPlay®, Apple CarPlay®/Android Auto®, Auto High...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/28 Highway)
Listing Information:
VIN: WDDUG6GBXLA517947
Stock: 844
Certified Pre-Owned: No
Listed since: 06-11-2025 - New Listing$100,795great price$14,606 below market
- 6,121 miles
- 18 City / 26 Hwy MPG
- CarMart (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: W1K6G7GB6RA299948
Stock: CM10936
Certified Pre-Owned: No
Listed since: 07-25-2025 - 46,121 miles
- 1 accident, 3 owners, personal use only
- 17 City / 25 Hwy MPG
- Auto Buying Service (158 mi away)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GBXMA019439
Stock: ABS8405
Certified Pre-Owned: No
Listed since: 07-09-2025- 39,566 miles
- Water damage reported, 1 owner, personal use only
- 17 City / 25 Hwy MPG
- Royal Auto Club (169 mi away)
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Located in Sterling, VA / 169 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GB8MA034585
Stock: SAI2478
Certified Pre-Owned: No- New Listing$87,998good price$4,850 below market
- 25,103 miles
- No accidents, 1 owner, personal use only
- 18 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
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Located in Lithia Springs, GA / 514 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: W1K6G7GB7RA262679
Stock: 27386575
Certified Pre-Owned: No - 29,889 miles
- No accidents, 1 owner, personal use only
- 17 City / 25 Hwy MPG
- iDeal Auto (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GB7MA050115
Stock: 16838A
Certified Pre-Owned: No- 22,803 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 17 City / 25 Hwy MPG
- iDeal Auto (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GBXMA035317
Stock: 16815
Certified Pre-Owned: No- $41,997fair price$1,760 below market
- 55,800 miles
- No accidents, 2 owners, personal use
- 17 City / 27 Hwy MPG
- Fred's Executive Auto (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
Check out this great value! Feature-packed and decked out! A turbocharger further enhances performance, while also preserving fuel economy. This 4 doo...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (17 City/27 Highway)
Listing Information:
VIN: WDDUG8DB3LA521600
Stock: 521600
Certified Pre-Owned: No
Listed since: 06-18-2025 - Price Drop$102,855fair price$2,380 below market
- 9,427 miles
- No accidents, personal use only
- 18 City / 26 Hwy MPG
- Porsche Wilmington (195 mi away)
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Located in Wilmington, NC / 195 miles away from Chesapeake, VA
2024 Mercedes-Benz S-Class S 580 4MATIC REMAINDER OF FACTORY WARRANTY, FACTORY MAINTENANCE UP TO DATE, NAVIGATION GPS, 19" AMG Twin 5-Spoke Wheels, 3D...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: W1K6G7GB3RA265675
Stock: PP9942
Certified Pre-Owned: No
Listed since: 05-16-2025 - New Listing$65,995good price$2,661 below market
- 9,793 miles
- No accidents, 1 owner, personal use
- 21 City / 30 Hwy MPG
- Kingstowne Motorcars (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
***BUY WITH CONFIDENCE, RATED *TOP 10 DEALER IN VIRGINIA* WOW ONLY 9K MILES!!! ONE OWNER / MSRP $119K / AMG LINE PKG / BURMESTER SOUND / 20-INCH WH...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/30 Highway)
Listing Information:
VIN: W1K6G6DB8NA121774
Stock: KTM7142
Certified Pre-Owned: No - $68,900good price$2,247 below market
- 18,245 miles
- No accidents, 2 owners, personal use only
- 21 City / 30 Hwy MPG
- Classic Chrysler Jeep Dodge Ram FIAT (134 mi away)
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Located in Goldsboro, NC / 134 miles away from Chesapeake, VA
Recent Arrival!Odometer is 18404 miles below market average!4MATIC, Leather.The 2022 Mercedes-Benz S 500 4MATIC is a flagship luxury sedan that exempl...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/30 Highway)
Listing Information:
VIN: W1K6G6DB3NA089283
Stock: CU235A
Certified Pre-Owned: No
Listed since: 04-24-2025 - $104,991fair price$2,901 above market
- 15,539 miles
- No accidents, 1 owner, rental vehicle
- 18 City / 26 Hwy MPG
- Mercedes-Benz of Richmond (95 mi away)
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Located in Richmond, VA / 95 miles away from Chesapeake, VA
Vehicle #23. Step into the realm of luxury with our selection of Nearly New Mercedes-Benz vehicles, where premium quality meets remarkable value. Each...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/26 Highway)
Listing Information:
VIN: W1K6G7GB0RA271661
Stock: 97423L
Certified Pre-Owned: Yes
Listed since: 12-31-2023 - 1,484 miles
- Lemon reported, 1 owner, personal use
- 16 City / 25 Hwy MPG
- Elite Auto Brokers (176 mi away)
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Located in Gaithersburg, MD / 176 miles away from Chesapeake, VA
SHOWROOM CONDITION! 2022 Mercedes S580 4MATIC with only 1K miles. Equipped with 20 Wheels, Front heated and ventilated seats with Massage, Blind Spot ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: Yes
Free History Report: No
Features and Specs:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GB6NA096889
Stock: 096889
Certified Pre-Owned: No
Listed since: 04-24-2025- $75,881fair price$98 below market
- 36,881 miles
- No accidents, 1 owner, personal use
- 16 City / 25 Hwy MPG
- Euro Motorcars Bethesda (162 mi away)
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Located in Bethesda, MD / 162 miles away from Chesapeake, VA
Clean CARFAX. 9-Speed Automatic 4.0L V8, 4MATIC , Silver Grey/Black Leather.Recent Arrival!4MATIC ***** We are offering this vehicle for sale. If you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GB8NA112462
Stock: A23717
Certified Pre-Owned: Yes
Listed since: 07-22-2025 - $67,881fair price$2,215 above market
- 41,331 miles
- No accidents, 1 owner, personal use only
- 21 City / 30 Hwy MPG
- Euro Motorcars Bethesda (162 mi away)
Close
Located in Bethesda, MD / 162 miles away from Chesapeake, VA
Clean CARFAX. Certified. 9-Speed Automatic 4MATIC , Black Leather.21/30 City/Highway MPG4MATIC Mercedes-Benz Details: * Warranty Deductible: $0 * Road...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/30 Highway)
Listing Information:
VIN: W1K6G6DBXNA067281
Stock: A23708
Certified Pre-Owned: Yes
Listed since: 07-11-2025 - Price Drop$82,336fair price$1,417 above market
- 33,639 miles
- No accidents, 1 owner, personal use
- 16 City / 25 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Los Angeles, CA / 2,356 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Ke...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GB8NA145106
Stock: 21014P
Certified Pre-Owned: No - New Listing$64,998fair price$1,093 below market
- 33,986 miles
- 21 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KS to VA*
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Located in Merriam, KS / 1,017 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
24 Combined MPG (21 City/30 Highway)
Listing Information:
VIN: W1K6G6DB2NA146900
Stock: 27612703
Certified Pre-Owned: No - Price Drop
- 39,938 miles
- No accidents, 2 owners, personal use only
- 16 City / 25 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
Close
Located in Lithia Springs, GA / 514 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GB8NA167090
Stock: 27300192
Certified Pre-Owned: No
Showing 43 - 63 out of 491 listings
Consumer Reviews for the Mercedes-Benz S-Class
Read recent reviews for the Mercedes-Benz S-Class
Beautiful looking but beware of quirks.....
sport sedan owner, 05/14/2023
2023 Mercedes-Benz S-Class S 500 4MATIC 4dr Sedan AWD (3.0L 6cyl Twincharger gas/electric mild hybrid 9A)
The car drives great when working. Its looks great and still turn heads, but in 5 months of ownership, it has been in service 3 times. The engine light has gone on with no answer as to what the problem is. The mechanism for the door to open, broke and we were unable to open the door. Lots of quirks to the software and even key to open the doors is suspect.
I hope Mercedes learns to be … reliable.
Used 2021 Mercedes-Benz S-Class in Chesapeake, VA Values
Estimated values
2021 Mercedes-Benz S-Class S 500 4MATIC 4dr Sedan AWD (3.0L 6cyl Twincharger gas/electric mild hybrid 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $57,903 | $59,840 | $61,793 |
| Clean | $56,676 | $58,467 | $60,268 |
| Average | $54,631 | $56,179 | $57,726 |
| Rough | $51,973 | $53,204 | $54,422 |
The average list price of a used 2021 Mercedes-Benz S-Class in Chesapeake, Virginia is $78,891. The average mileage on a used Mercedes-Benz S-Class 2021 for sale in Chesapeake, Virginia is 29,713. Based on the average mileage of 29,713 for used 2021 Mercedes-Benz S-Class for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Mercedes-Benz S-Class 2021 in Chesapeake, Virginia to be $54,631.
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