Skip to FiltersReport abuse
480 listings
- $40,618fair price$159 below market
- 52,129 miles
- 1 accident, 2 owners, personal use
- 17 City / 27 Hwy MPG
- Auto Haus (34 mi away)
Close
Located in Yorktown, VA / 34 miles away from Chesapeake, VA
4MATIC , Porcelain/Black w/Perforated Nappa Leather Upholstery, Active Distance Assist DISTRONIC , Active Lane Change Assist, Active Parking Assist, A...
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:
21 Combined MPG (17 City/27 Highway)
Listing Information:
VIN: WDDUG8GB2KA465837
Stock: W13641
Certified Pre-Owned: No
Listed since: 04-25-2025 - $27,995fair price$562 above market
- 52,419 miles
- No accidents, 4 owners, corporate fleet vehicle
- 17 City / 26 Hwy MPG
- Maximum Auto Outlet (155 mi away)
Close
Located in Manassas, VA / 155 miles away from Chesapeake, VA
***LOW MILEAGE, BEAUTIFUL MERCEDES-BENZ LUXURY SEDAN WITH DUAL ROOFS, SURROUND VIEW CAMERA SYSTEM, AND ALL THE OPTIONS.............................201...
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: WDDUG8CB0FA174409
Stock: FA174409
Certified Pre-Owned: No - Price Drop$39,990fair price$1,831 below market
- 49,250 miles
- 1 accident, 5 owners, personal use
- 8cyl automatic
- Carvana (In-stock online)
- Home delivery*
Close
Located in Oklahoma City, OK / 1,189 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:
19 Combined MPG (16 City/24 Highway)
Listing Information:
VIN: WDDXJ8FB8FA010836
Stock: 2003722405
Certified Pre-Owned: No
Listed since: 05-10-2025 - New Listing$38,998fair price$1,028 below market
- 43,555 miles
- 3 accidents, 2 owners, personal use
- 8cyl automatic
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Bakersfield, CA / 2,374 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: No
Features and Specs:
19 Combined MPG (16 City/24 Highway)
Listing Information:
VIN: WDDXJ8FB3FA010744
Stock: 26397078
Certified Pre-Owned: No - New Listing
- 52,285 miles
- No accidents, 3 owners, personal use
- 17 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
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$45,998fair price$990 above market
- 45,476 miles
- No accidents, 2 owners, personal use
- 17 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in San Jose, CA / 2,493 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:
21 Combined MPG (17 City/27 Highway)
Listing Information:
VIN: WDDUG8DB3KA433645
Stock: 27288421
Certified Pre-Owned: No - $38,990fair price$354 above market
- 50,297 miles
- No accidents, 2 owners, personal use
- 19 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 707 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:
22 Combined MPG (19 City/28 Highway)
Listing Information:
VIN: WDDUG6GB5KA495158
Stock: 2003735440
Certified Pre-Owned: No
Listed since: 05-13-2025 - New Listing$40,590fair price
- 51,658 miles
- No accidents, 1 owner, personal use only
- 8cyl automatic
- 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/24 Highway)
Listing Information:
VIN: WDDXJ8FB3FA002188
Stock: 2003639622
Certified Pre-Owned: No
Listed since: 04-07-2025 - $17,995fair price$490 above market
- 158,105 miles
- 1 accident, 5 owners, personal use
- 16 City / 26 Hwy MPG
- Ram Motors (88 mi away)
Close
Located in Richmond, VA / 88 miles away from Chesapeake, VA
VA DEALER PLUS TAX TAGS AND DEALER PROCESS FEE OF $200 .
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/26 Highway)
Listing Information:
VIN: WDDUG8FBXFA127934
Stock: 127934RR
Certified Pre-Owned: No
Listed since: 05-03-2025 - $47,990good price$3,419 below market
- 25,217 miles
- 2 accidents, 3 owners, corporate fleet vehicle
- 17 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Birmingham, AL / 637 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: 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: WDDUG8GB6KA462682
Stock: 2003680417
Certified Pre-Owned: No
Listed since: 05-06-2025 - New Listing$35,997fair price$65 above market
- 89,443 miles
- 1 accident, 2 owners, personal use only
- 17 City / 27 Hwy MPG
- S & S Auto Sales (8 mi away)
Close
Located in Virginia Beach, VA / 8 miles away from Chesapeake, VA
V8, Twin Turbo, 4.0 Liter, Automatic, 9-Spd 9G-Tronic, RWD, AMG Line Exterior Pkg, Blind-Spot Assist, Driver Assistance Pkg, Premium Pkg, Warmth & Com...
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:
21 Combined MPG (17 City/27 Highway)
Listing Information:
VIN: WDDUG8DB2KA479791
Stock: 286
Certified Pre-Owned: No - Price Drop
- 97,099 miles
- 1 accident, 4 owners, personal use only
- 15 City / 24 Hwy MPG
- Merlex Auto Group (156 mi away)
Close
Located in Arlington, VA / 156 miles away from Chesapeake, VA
This vehicle is subject to prior sale. The pricing, equipment, specifications, and photos presented are believed to be accurate, but are provided \\AS...
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/24 Highway)
Listing Information:
VIN: WDDNG9EB2DA517435
Stock: 517435
Certified Pre-Owned: No
Listed since: 04-29-2025 - 124,516 miles
- No accidents, 2 owners, personal use only
- 16 City / 26 Hwy MPG
- Best Buy Wheels (13 mi away)
Close
Located in Virginia Beach, VA / 13 miles away from Chesapeake, VA
Best Buy Wheels online at WWW.BBWAUTOS.COM to see more pictures for this vehicle in addition to the CARFAX. Over 10 years of experience with providing...
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: WDDUG8FB2FA107421
Stock: 107421
Certified Pre-Owned: No
Listed since: 11-12-2024- 18,870 miles
- No accidents, 3 owners, personal use only
- 8cyl automatic
- 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/24 Highway)
Listing Information:
VIN: WDDXJ8FB5FA005755
Stock: 2003726887
Certified Pre-Owned: No
Listed since: 05-13-2025- New Listing$31,990fair price$880 above market
- 53,727 miles
- 17 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Oklahoma City, OK / 1,189 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 Unavailable.
Features and Specs:
20 Combined MPG (17 City/26 Highway)
Listing Information:
VIN: WDDUG8CB6FA131239
Stock: 2003775327
Certified Pre-Owned: No
Listed since: 06-07-2025 - 35,612 miles
- No accidents, 2 owners, personal use only
- 17 City / 27 Hwy MPG
- Mercedes-Benz of Virginia Beach (8 mi away)
Close
Located in Virginia Beach, VA / 8 miles away from Chesapeake, VA
Recent Arrival! Clean CARFAX.Certified. Selenite Gray Metallic 2019 Mercedes-Benz S-Class S 560 RWD 9-Speed Automatic 4.0L V8Magma Gray/Espresso Brown...
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: WDDUG8DB5KA425420
Stock: Z5874A
Certified Pre-Owned: Yes
Listed since: 04-17-2025- Price Drop$51,590fair price$1,338 above market
- 22,366 miles
- No accidents, 2 owners, personal use
- 17 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 707 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:
21 Combined MPG (17 City/27 Highway)
Listing Information:
VIN: WDDUG8DB6KA425524
Stock: 2003734687
Certified Pre-Owned: No
Listed since: 05-16-2025 - New Listing
- 23,926 miles
- No accidents, 1 owner, personal use only
- 18 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Sacramento, CA / 2,452 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:
22 Combined MPG (18 City/28 Highway)
Listing Information:
VIN: WDDUG6EB0KA445383
Stock: 2003633325
Certified Pre-Owned: No
Listed since: 04-08-2025 - 31,560 miles
- No accidents, 2 owners, personal use
- 15 City / 24 Hwy MPG
- Select Auto Imports (151 mi away)
Close
Located in Alexandria, VA / 151 miles away from Chesapeake, VA
Original MSRP $102,120.00*Complete Pre-Purchase Inspection has been performed on the car.*Complete "Service B" has just been performed on the car....
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/24 Highway)
Listing Information:
VIN: WDDNG9EB8DA527922
Stock: 22880
Certified Pre-Owned: No
Listed since: 05-24-2025- 124,030 miles
- No accidents, 5 owners, personal use
- 16 City / 26 Hwy MPG
- VCD Auto Group (169 mi away)
Close
Located in Sterling, VA / 169 miles away from Chesapeake, VA
2015 Mercedes-Benz S550 4MATIC Elegance, Power, and Proven Reliability124,200 miles | VIN: WDDUG8FB4FA107095Experience top-tier luxury and performance...
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: WDDUG8FB4FA107095
Stock: 053
Certified Pre-Owned: No
Listed since: 06-04-2025- 25,198 miles
- No accidents, 1 owner, personal use
- 17 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Royal Palm Beach, FL / 733 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 (17 City/27 Highway)
Listing Information:
VIN: WDDUG8DB3KA496311
Stock: 26974162
Certified Pre-Owned: No
Showing 232 - 252 out of 480 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 2019 Mercedes-Benz S-Class in Chesapeake, VA Values
Estimated values
2019 Mercedes-Benz S-Class S 560 4MATIC 4dr Sedan AWD (4.0L 8cyl Turbo 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $37,680 | $41,679 | $45,262 |
| Clean | $36,591 | $40,427 | $43,853 |
| Average | $34,776 | $38,342 | $41,505 |
| Rough | $32,416 | $35,631 | $38,452 |
The average list price of a used 2019 Mercedes-Benz S-Class in Chesapeake, Virginia is $37,088. The average mileage on a used Mercedes-Benz S-Class 2019 for sale in Chesapeake, Virginia is 58,416. Based on the average mileage of 58,416 for used 2019 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 2019 in Chesapeake, Virginia to be $34,776.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
EV Details
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.