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502 listings
- Price Drop$68,000good price$3,053 below market
- 21,305 miles
- No accidents, 2 owners, corporate fleet vehicle
- 17 City / 25 Hwy MPG
- Farrish Chrysler Dodge Jeep Ram (158 mi away)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
JUST IN!! **2021 MERCEDES S580 4MATIC** ONLY 21K MILES** STILL UNDER FACTORY WARRANTY** LUXURY LINE** 20" WHEELS** BLACK NAPPA LEATHER DIAMOND INTERIO...
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:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GBXMA034250
Stock: PZ12821
Certified Pre-Owned: No
Listed since: 04-02-2025 - $55,999good price$2,829 below market
- 82,827 miles
- No accidents, 1 owner, personal use only
- 17 City / 25 Hwy MPG
- Metri Motors (154 mi away)
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Located in Raleigh, NC / 154 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: W1K6G7GBXMA045183
Stock: 045183
Certified Pre-Owned: No - New Listing$66,000fair price$839 below market
- 43,032 miles
- No accidents, 2 owners, personal use
- 17 City / 25 Hwy MPG
- Ourisman Chrysler Dodge Jeep Ram (176 mi away)
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Located in Clarksville, MD / 176 miles away from Chesapeake, VA
CARFAX One-Owner.Clean CARFAX. This 2021 Graphite Gray Metallic Mercedes-Benz S-Class S 580 AWD 4MATIC® is well equipped and includes these features ...
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: W1K6G7GBXMA041246
Stock: M04552
Certified Pre-Owned: No
Listed since: 07-10-2025 - New Listing
- 41,692 miles
- Insurance loss reported, 2 owners, taxi vehicle
- 17 City / 25 Hwy MPG
- Pride Auto Sales (126 mi away)
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Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
*Auto Park* *Dual Moonroof* *Keyless Start* *Massage Seats* *Power Liftgate* *Premium Sound System* 3 months or 3,000 miles warranty included on selec...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
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:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GB8MA033128
Stock: 033128
Certified Pre-Owned: No - 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
- 46,121 miles
- 1 accident, 3 owners, personal use only
- 17 City / 25 Hwy MPG
- Auto Buying Service (158 mi away)
Close
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 - $63,800great price$7,981 below market
- 55,287 miles
- No accidents, 1 owner, personal use
- 16 City / 25 Hwy MPG
- Hanna Imports (148 mi away)
Close
Located in Raleigh, NC / 148 miles away from Chesapeake, VA
CARFAX One-Owner. *Multi Point Inspection*, *Carfax Accident Free*, 4.0L V8, 4MATIC®, Macchiato/Magma Gray w/Nappa Leather Upholstery, 3D Instrument C...
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: W1K6G7GB8NA072464
Stock: 3021500
Certified Pre-Owned: No
Listed since: 04-17-2025 - 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- $33,950great price$5,379 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 - Price Drop$66,000good price$5,608 below market
- 37,034 miles
- 1 accident, 1 owner, personal use
- 16 City / 25 Hwy MPG
- Auto Giants Nissan (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
Summer is Heating Up!2022 Mercedes-Benz S-Class S 580 4MATIC® GrayKEY FEATURES INCLUDED:, AWD, APPLE CARPLAY, ANDROID AUTO, TOUCHSCREEN/ INFOTAINMENT,...
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:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GBXNA118814
Stock: G2212
Certified Pre-Owned: No
Listed since: 05-30-2025 - 29,889 miles
- No accidents, 1 owner, personal use only
- 17 City / 25 Hwy MPG
- iDeal Auto (144 mi away)
Close
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)
Close
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- 19,726 miles
- Lemon reported, 1 owner, personal use
- 16 City / 25 Hwy MPG
- VINS (156 mi away)
Close
Located in Manassas Park, VA / 156 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! 2022 Mercedes-Benz S-Class S 580 MANUFAKTUR Diamond White 4.0L V8 $131K MSRP, $12K Options, 4.0L V8, 4MATIC®, Bl...
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: W1K6G7GB0NA128073
Stock: 23155
Certified Pre-Owned: No
Listed since: 06-04-2025- $25,163great price$8,474 below market
- 96,029 miles
- No accidents, 1 owner, personal use only
- 17 City / 27 Hwy MPG
- Carget Motors (143 mi away)
Close
Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
This 2019 Mercedes-Benz S 560 Sedan represents the pinnacle of luxury, sophistication, and performance in the executive class. Finished in an elegant ...
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: WDDUG8DB2KA442546
Stock: 442546
Certified Pre-Owned: No
Listed since: 05-27-2025 - $42,997fair price$229 above market
- 55,800 miles
- No accidents, 2 owners, personal use
- 17 City / 27 Hwy MPG
- Fred's Executive Auto (143 mi away)
Close
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 - New Listing
- 17,913 miles
- Insurance loss reported, 1 owner, personal use only
- 16 City / 25 Hwy MPG
- Pride Auto Sales (126 mi away)
Close
Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
*Executive Rear Seat Package* *3D Technology Package* *Warmth & Comfort Package* *Executive Line* *Heads-Up Display* *CarPlay* *Massage Seats* *Heated...
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: W1K6G7GB4NA138220
Stock: 138220
Certified Pre-Owned: No - 12,027 miles
- Frame damage reported, 1 owner, corporate fleet vehicle
- 16 City / 25 Hwy MPG
- Auto Buying Service (158 mi away)
Close
Located in Fairfax, VA / 158 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GB0NA148047
Stock: ABS8233
Certified Pre-Owned: No
Listed since: 05-27-2025- New Listing$59,995fair price$217 below market
- 58,779 miles
- 21 City / 30 Hwy MPG
- Universal Auto Group (163 mi away)
Close
Located in Silver Spring, MD / 163 miles away from Chesapeake, VA
$133,450 ORIGINAL MSRP CLEAN CARFAX GREAT SERVICE HISTORY 4 NEW TIRES PROFESSIONALLY DETAILED 105 POINT MARYLAND STATE INSPECTION COMPLETE
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
24 Combined MPG (21 City/30 Highway)
Listing Information:
VIN: W1K6G6DB0NA073851
Stock: 17722
Certified Pre-Owned: No
Listed since: 07-11-2025 - Price Drop
- 37,782 miles
- No accidents, 1 owner, personal use
- 18 City / 28 Hwy MPG
- CarMax Virginia Beach (10 mi away)
Close
Located in Virginia Beach, VA / 10 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:
22 Combined MPG (18 City/28 Highway)
Listing Information:
VIN: WDDUG6EB1LA515569
Stock: 27565320
Certified Pre-Owned: No - New Listing
- 24,917 miles
- No accidents, 1 owner, corporate fleet vehicle
- 16 City / 25 Hwy MPG
- CarMax Frederick (173 mi away)
Close
Located in Gaithersburg, MD / 173 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: 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:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: W1K6G7GB9NA137063
Stock: 27524057
Certified Pre-Owned: No - 19,053 miles
- No accidents, 2 owners, personal use
- 21 City / 30 Hwy MPG
- Genesis of Annapolis (156 mi away)
Close
Located in Annapolis, MD / 156 miles away from Chesapeake, VA
This S500 was driven in Delaware and traded for a new Genesis. It is fully inspected and freshly serviced. Some options include; Cooled Seats, Heated ...
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: W1K6G6DB3NA067932
Stock: G357A
Certified Pre-Owned: No
Listed since: 05-23-2025
Showing 1 - 21 out of 502 listings
Consumer Reviews for the Mercedes-Benz S-Class
Read recent reviews for the Mercedes-Benz S-Class
never in 21 yrs given MB less than 5 stars, but...
P M, 04/14/2020
2019 Mercedes-Benz S-Class S 450 4MATIC 4dr Sedan AWD (3.0L 6cyl Turbo 9A)
I guess every maker has a bad year. I think it’s MB’s turn. I’ve had this new 2019 S560 4matic sedan 5 months, and all 5, battled operational and technology issues, PLUS, a dealer who has REFUSED to fix the car! And MBUSA has refused to get in the middle. The car will not shift - 3 times in one day, it’s confused, won’t shift into park, and the shifter operates the NAV screen! I felt … like I was being taken over by a machine in Terminator and my car was rebelling. Many technology issues, such as not using a contact for directions - it tells me info is missing, even though it’s there. Won’t load all my contacts (yes, I’ve done everything all the books and MB says), my doors suddenly won’t unlock and I have the key fob. All except technology failures, are intermittent but enough I can not trust the car again. It doesn’t help the dealer actually refused to take the car, won’t send anyone to view the problems so I can create them, MB executive relations won’t get in the middle, and I’m stuck with a car I rightly can’t trust to drive.
Used 2021 Mercedes-Benz S-Class in Chesapeake, VA Values
Estimated values
2021 Mercedes-Benz S-Class S 580 4MATIC 4dr Sedan AWD (4.0L 8cyl Turbo gas/electric mild hybrid 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $57,601 | $60,506 | $63,437 |
| Clean | $56,380 | $59,118 | $61,871 |
| Average | $54,346 | $56,804 | $59,262 |
| Rough | $51,702 | $53,797 | $55,870 |
The average list price of a used 2021 Mercedes-Benz S-Class in Chesapeake, Virginia is $63,661. The average mileage on a used Mercedes-Benz S-Class 2021 for sale in Chesapeake, Virginia is 41,901. Based on the average mileage of 41,901 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 $54,346.
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