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487 listings
- $68,000good price$5,277 below market
- 32,816 miles
- No accidents, 1 owner, personal use
- 17 City / 25 Hwy MPG
- Mercedes-Benz of Fredericksburg (129 mi away)
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Located in Fredericksburg, VA / 129 miles away from Chesapeake, VA
This 2021 Selenite Gray Metallic Mercedes-Benz S-Class S 580 AWD 4MATIC® is well equipped and includes these features and benefits: Certified.Clean ...
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: W1K6G7GB5MA038724
Stock: 156031M
Certified Pre-Owned: Yes
Listed since: 04-26-2025 - Not Priced
- 95,871 miles
- 1 accident, 3 owners, personal use
- 17 City / 26 Hwy MPG
- AMKO Auto Temple Hills (149 mi away)
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Located in Temple Hills, MD / 149 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/26 Highway)
Listing Information:
VIN: WDDUG8CB7GA210033
Stock: 24268
Certified Pre-Owned: No
Listed since: 05-30-2025 - New ListingNot Priced
- 132,804 miles
- 1 accident, 3 owners, personal use only
- 17 City / 25 Hwy MPG
- Automan Empire (126 mi away)
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Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
2014 MERCEDES-BENZ S-CLASS S 550 with powerful 4.6L DOHC 32V DIRECT-INJECTION V8 engine and driven only 0 miles! Fully loaded and much more! CARFAX CE...
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: WDDUG8CB2EA044789
Stock: X44789
Certified Pre-Owned: No - New Listing$60,990good price
- 27,129 miles
- 1 accident, 4 owners, personal use
- 8cyl automatic
- Carvana (In-stock online)
- Home delivery*
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Located in Houston, TX / 1,213 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
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:
18 Combined MPG (15 City/23 Highway)
Listing Information:
VIN: WDDXJ7JB6FA000999
Stock: 2003753834
Certified Pre-Owned: No
Listed since: 06-02-2025 - New Listing$32,990great price$4,008 below market
- 55,399 miles
- 18 City / 28 Hwy MPG
- Antwerpen Chrysler Jeep Dodge Ram (178 mi away)
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Located in Baltimore, MD / 178 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
22 Combined MPG (18 City/28 Highway)
Listing Information:
VIN: WDDUG6EB6KA464777
Stock: 1117P
Certified Pre-Owned: No
Listed since: 06-12-2025 - Price Drop$68,999good price$3,523 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 - New Listing$56,999good price$3,967 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 - Price Drop$16,985fair price$1,470 below market
- 84,320 miles
- No accidents, 3 owners, corporate fleet vehicle
- 15 City / 25 Hwy MPG
- Trimax Auto (11 mi away)
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Located in Norfolk, VA / 11 miles away from Chesapeake, VA
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 (15 City/25 Highway)
Listing Information:
VIN: WDDNG7DB7DA511622
Stock: TR3172
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$42,980good price$4,078 below market
- 34,400 miles
- No accidents, 2 owners, personal use only
- 17 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Verona, NJ / 303 miles away from Chesapeake, VA
CarFax No Accidents Reported,Low Mileage,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keepin...
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: WDDUG8GB7KA463940
Stock: MAJ3540
Certified Pre-Owned: No - Price Drop$42,444good price$3,115 below market
- 41,202 miles
- No accidents, 2 owners, taxi vehicle
- 17 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Sherman Oaks, CA / 2,363 miles away from Chesapeake, VA
Low Mileage,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Leather Seats,Naviga...
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 (17 City/27 Highway)
Listing Information:
VIN: WDDUG8DB0KA435658
Stock: KA435658T
Certified Pre-Owned: No - Price Drop$65,998fair price$1,949 below market
- 41,395 miles
- No accidents, 2 owners, personal use
- 17 City / 25 Hwy MPG
- CarMax Dulles (170 mi away)
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Located in Sterling, VA / 170 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:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GB2MA047929
Stock: 27276068
Certified Pre-Owned: No - Price Drop$63,000good price$2,104 below market
- 66,719 miles
- No accidents, 3 owners, corporate fleet vehicle
- 17 City / 26 Hwy MPG
- Ourisman Jeep (161 mi away)
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Located in Bethesda, MD / 161 miles away from Chesapeake, VA
2019 Mercedes-Benz S-Class S 63 AMG 4MATIC 4MATIC designo Cashmere White Magno (Matte Finish) NAVIGATION / GPS / NAV, APPLE CAR PLAY / ANDROID AUTO, M...
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/26 Highway)
Listing Information:
VIN: WDDUG8JB3KA438297
Stock: PA438297
Certified Pre-Owned: No
Listed since: 04-14-2025 - New Listing
Photos not available$21,990fair price$957 below market- 111,183 miles
- No accidents, 3 owners, personal use
- 16 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
Step into a world of unparalleled luxury and performance with this stunning 2015 Mercedes-Benz S550V4, a masterpiece of automotive engineering that co...
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/26 Highway)
Listing Information:
VIN: WDDUG8FB1FA146954
Stock: M6796
Certified Pre-Owned: No
Listed since: 06-07-2025 - Price Drop$64,998fair price$1,754 below market
- 47,576 miles
- No accidents, 3 owners, personal use
- 17 City / 25 Hwy MPG
- CarMax Winchester (197 mi away)
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Located in Winchester, VA / 197 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:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: W1K6G7GB8MA039155
Stock: 27313892
Certified Pre-Owned: No - Price Drop$41,988fair price$1,404 below market
- 54,715 miles
- No accidents, 4 owners, personal use
- 15 City / 23 Hwy MPG
- Rolls-Royce Motor Cars Raleigh (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
2015 Mercedes-Benz S-Class S 63 AMG 4MATIC 5.5L V8 DOHC 32V Bi-Turbocharged 4MATIC 7-Speed Automatic 15/23 City/Highway MPG Silver Come See this Merce...
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:
18 Combined MPG (15 City/23 Highway)
Listing Information:
VIN: WDDUG7JB8FA154311
Stock: R5495K
Certified Pre-Owned: No
Listed since: 04-08-2025 - New Listing
- 52,285 miles
- No accidents, 3 owners, personal use
- 17 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Houston, TX / 1,213 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts 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:
20 Combined MPG (17 City/26 Highway)
Listing Information:
VIN: WDDUG8CB6FA130138
Stock: 2003757446
Certified Pre-Owned: No
Listed since: 05-24-2025 - Price Drop$38,735fair price$516 below market
- 65,002 miles
- No accidents, 2 owners, corporate fleet vehicle
- 17 City / 27 Hwy MPG
- Nissan of Rocky Mount (103 mi away)
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Located in Rocky Mount, NC / 103 miles away from Chesapeake, VA
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 (17 City/27 Highway)
Listing Information:
VIN: WDDUG8DB7KA476840
Stock: P24545A
Certified Pre-Owned: No
Listed since: 03-28-2025 - New Listing$29,590fair price
- 57,683 miles
- No accidents, 5 owners, personal use
- 16 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 1,195 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts 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/26 Highway)
Listing Information:
VIN: WDDUG8FB8FA105947
Stock: 2003351898
Certified Pre-Owned: No
Listed since: 12-07-2024 - New Listing$38,990fair price$905 below market
- 57,182 miles
- No accidents, 4 owners, personal use only
- 8cyl automatic
- Carvana (In-stock online)
- Home delivery*
Close
Located in Portland, OR / 2,455 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts 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/24 Highway)
Listing Information:
VIN: WDDXJ8FB8FA006690
Stock: 2003578031
Certified Pre-Owned: No
Listed since: 03-14-2025 - Price Drop$41,998fair price$2,570 below market
- 57,725 miles
- 1 accident, 3 owners, personal use
- 17 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to VA*
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Located in Las Vegas, NV / 2,152 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: 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: Yes
Features and Specs:
21 Combined MPG (17 City/27 Highway)
Listing Information:
VIN: WDDUG8GB9KA459386
Stock: 26880365
Certified Pre-Owned: No - $24,900fair price$678 above market
- 99,261 miles
- No accidents, 7 owners, personal use
- 16 City / 26 Hwy MPG
- Maguire and Sons Auto Brokers Inc (6 mi away)
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Located in Virginia Beach, VA / 6 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:
19 Combined MPG (16 City/26 Highway)
Listing Information:
VIN: WDDUG8FB7FA108614
Stock: 25027T
Certified Pre-Owned: No
Listed since: 12-31-2024
Showing 211 - 231 out of 487 listings
Consumer Reviews for the Mercedes-Benz S-Class
Read recent reviews for the Mercedes-Benz S-Class
Too much, too often
Walter, 09/07/2019
2017 Mercedes-Benz S-Class S 550 4dr Sedan (4.7L 8cyl Turbo 9A)
The qualifier. I have had almost everything, Cadillac, Jaguar XJL, Rolls Royce, Lincoln, BMW, Lexus and Infinity and several Mercedes - all the upper end models. This 2017 S 550 has to go into the shop too often and costs too much. Brakes and rotors, $2,400, windshield wipers $200, tires (9 of them) at $438 because the run flats bubble when you hit a bump. Engineers say it is because … of Houston streets. I ask you, if you buy a $110,000 car in Houston, where do they expect you to drive it? They should designate different tires and solve the porblem. Left turn signal cornering light, $3,567.00, you have to replace the entire assembly. Steering wheel got stuck in the up and extended position. I felt like I was driving a Metro Bus until I got it in the shop. Satellite system went out and had to be replaced. Console retracting door gets stuck. It really goes on and on. Some of it covered under warranty and some of it not but you still have to take it in. I am stuck in a lease until March of 2020 and that will be the last Mercedes. Captain of Industry or Captain Dummy? I can afford it, but I just can't deal with it. Sometimes I think they count on us putting up with that nonsense. It is my fault for buying one, but never, I mean never again. Rolls Royce and Lexus do much better.
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 | $47,585 | $50,960 | $54,366 |
| Clean | $46,576 | $49,790 | $53,024 |
| Average | $44,896 | $47,842 | $50,788 |
| Rough | $42,711 | $45,309 | $47,881 |
The average list price of a used 2021 Mercedes-Benz S-Class in Chesapeake, Virginia is $44,924. The average mileage on a used Mercedes-Benz S-Class 2021 for sale in Chesapeake, Virginia is 62,800. Based on the average mileage of 62,800 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 $44,896.
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