Skip to main content
Skip to Filters
475 listings
  • New Listing
    • 82,928 miles
    • 11 City / 17 Hwy MPG
    • Sheehy INFINITI of Annapolis (159 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Annapolis, MD / 159 miles away from Chesapeake, VA

    2009 Mercedes-Benz S-Class S 63 AMG RWD at Sheehy Toyota of Fredericksburg! This S-Class has an exterior color of with Leather interior. This preown...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    13 Combined MPG (11 City/17 Highway)

    Listing Information:

    VIN: WDDNG77X59A271145
    Stock: F9334VB
    Certified Pre-Owned: No
    Listed since: 05-30-2025

  • $12,998
    good price
    $2,841 below market
    • 80,613 miles
    • No accidents, 2 owners, personal use
    • 15 City / 25 Hwy MPG
    • Atlantic Auto Sales (152 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Garner, NC / 152 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 (15 City/25 Highway)

    Listing Information:

    VIN: WDDNG7DB4CA467187
    Stock: 467187
    Certified Pre-Owned: No
    Listed since: 05-05-2025

  • Price Drop
    $22,995
    great price
    $3,008 below market
    • 56,665 miles
    • 2 accidents, 3 owners, personal use
    • 16 City / 26 Hwy MPG
    • Auto Buying Service (158 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    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:

    19 Combined MPG (16 City/26 Highway)

    Listing Information:

    VIN: WDDUG8FB5EA042742
    Stock: ABS7884
    Certified Pre-Owned: No
    Listed since: 03-04-2025

  • $9,999
    fair price
    $1,848 below market
    • 117,149 miles
    • No accidents, 1 owner, personal use only
    • 14 City / 21 Hwy MPG
    • A&R Auto Sales of Raleigh (146 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Upgraded Headlights
    Close

    Located in Raleigh, NC / 146 miles away from Chesapeake, VA

    Visit A+R Automotive to shop our great deals. You can contact us or call 9**-5**-1*** to schedule your test drive today.

    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:

    16 Combined MPG (14 City/21 Highway)

    Listing Information:

    VIN: WDDNG71X88A215952
    Stock: A215953
    Certified Pre-Owned: No
    Listed since: 12-18-2024

  • New Listing
    $15,995
    good price
    $1,301 below market
    • 74,243 miles
    • No accidents, 2 owners, personal use
    • 15 City / 25 Hwy MPG
    • Car Bros (9 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Virginia Beach, VA / 9 miles away from Chesapeake, VA

    2012 Mercedes-Benz S550 Car Bros 604 Newtown Rd VA Beach, VA 23462 Phone: (7**)4**-0*** www.carbrosva.com 2 Previous Owners ***74k Miles*** Heated Lea...

    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 (15 City/25 Highway)

    Listing Information:

    VIN: WDDNG7DB7CA471587
    Stock: 471587
    Certified Pre-Owned: No
    Listed since: 03-30-2025

  • New Listing
    $15,095
    good price
    $2,352 below market
    • 115,063 miles
    • 1 accident, 7 owners, corporate fleet vehicle
    • 17 City / 25 Hwy MPG
    • Carplug of Alexandria (151 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Upgraded Headlights
    Close

    Located in Alexandria, VA / 151 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: WDDUG8CB2EA012683
    Stock: CP4154
    Certified Pre-Owned: No

  • New Listing
    $27,990
    fair price
    $2,230 below market
    • 62,587 miles
    • No accidents, 5 owners, personal use only
    • 15 City / 23 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Phoenix, AZ / 2,024 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:

    18 Combined MPG (15 City/23 Highway)

    Listing Information:

    VIN: WDDNG7EB6CA475502
    Stock: 2003742511
    Certified Pre-Owned: No
    Listed since: 05-16-2025

  • $16,995
    fair price
    $740 below market
    • 126,041 miles
    • No accidents, 1 owner, personal use
    • 17 City / 25 Hwy MPG
    • Auto Buying Service (158 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Upgraded Headlights
    Close

    Located in Fairfax, VA / 158 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: WDDUG8CB6EA049364
    Stock: ABS7909
    Certified Pre-Owned: No
    Listed since: 03-10-2025

  • $11,498
    fair price
    $1,361 below market
    • 65,903 miles
    • No accidents, 3 owners, personal use
    • 14 City / 20 Hwy MPG
    • Next Car Imports (152 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Raleigh, NC / 152 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:

    16 Combined MPG (14 City/20 Highway)

    Listing Information:

    VIN: WDDNG86X88A173300
    Stock: 173300
    Certified Pre-Owned: No
    Listed since: 06-22-2024

  • Price Drop
    $8,900
    fair price
    $254 below market
    • 123,477 miles
    • No accidents, 2 owners, personal use only
    • 14 City / 20 Hwy MPG
    • Auto Bank II (158 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Fairfax, VA / 158 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:

    16 Combined MPG (14 City/20 Highway)

    Listing Information:

    VIN: WDDNG86X08A185022
    Stock: 185022
    Certified Pre-Owned: No

  • $19,999
    fair price
    $280 below market
    • 98,102 miles
    • No accidents, 5 owners, personal use
    • 15 City / 23 Hwy MPG
    • All Ryde (100 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Powhatan, VA / 100 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:

    18 Combined MPG (15 City/23 Highway)

    Listing Information:

    VIN: WDDNG7EB6CA436747
    Stock: 1029
    Certified Pre-Owned: No
    Listed since: 07-26-2024

  • Price Drop
    $21,900
    fair price
    $918 below market
    • 81,397 miles
    • No accidents, 3 owners, personal use
    • 16 City / 26 Hwy MPG
    • Mercedes-Benz of Silver Spring (167 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Silver Spring, MD / 167 miles away from Chesapeake, VA

    NEW ARRIVAL!!! PREMIUM 1 PKG... DRIVER ASSIST PKG... SURROUND VIEW CAMERA... HEATED STEERING WHEEL... 19" 5-SPOKE WHEEL... BURL WALNUT WOOD TRIM... M...

    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: WDDUG8FB4EA033403
    Stock: JP73739A
    Certified Pre-Owned: No
    Listed since: 05-06-2025

  • $19,876
    good price
    $2,108 below market
    • 88,475 miles
    • 3 accidents, 4 owners, personal use
    • 17 City / 25 Hwy MPG
    • 1st Auto Gallery (136 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Upgraded Headlights
    Close

    Located in Stafford, VA / 136 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: WDDUG8CB8EA066845
    Stock: AG-119
    Certified Pre-Owned: No

  • $12,995
    fair price
    $865 above market
    • 125,869 miles
    • No accidents, 4 owners, personal use
    • 15 City / 24 Hwy MPG
    • Auto Land (12 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Virginia Beach, VA / 12 miles away from Chesapeake, VA

    The 2012 Mercedes-Benz S550 4MATIC is a luxury sedan known for its blend of performance, comfort, and advanced technology. It features a 4.6-liter twi...

    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: WDDNG9EB3CA422896
    Stock: 422896
    Certified Pre-Owned: No
    Listed since: 10-17-2024

  • $24,995
    fair price
    $86 below market
    • 86,559 miles
    • No accidents, 5 owners, personal use
    • 16 City / 26 Hwy MPG
    • InTouch Auto Outlet (126 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Spotsylvania Courthouse, VA / 126 miles away from Chesapeake, VA

    *** PREMIUM ONE PACKAGE, BURMESTER HIGH END 3 D SURROUND SYSTEM,NIGHT VIEW ASSIST PLUS, WARMTH & COMFORT PACKAGE, SPORT PACKAGE PLUS ONE, 20 Inch Plu...

    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: WDDUG8FB8EA051063
    Stock: A4974
    Certified Pre-Owned: No

  • New Listing
    $14,296
    good price
    $1,183 below market
    • 139,855 miles
    • 1 accident, 2 owners, corporate fleet vehicle
    • 17 City / 25 Hwy MPG
    • CarPlug (132 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Upgraded Headlights
    Close

    Located in Fredericksburg, VA / 132 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: WDDUG8CB4EA027279
    Stock: AC3903
    Certified Pre-Owned: No

  • $10,999
    fair price
    $601 above market
    • 97,894 miles
    • No accidents, 3 owners, personal use only
    • 14 City / 20 Hwy MPG
    • Real Deal Auto Company (120 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in King George, VA / 120 miles away from Chesapeake, VA

    2008 MERCEDES-BENZ S-CLASS ALL WHEEL DRIVE with powerful 5.5L SFI DOHC 32-VALVE V8 engine and driven only 9789 miles! Fully loaded and much more! **FI...

    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:

    16 Combined MPG (14 City/20 Highway)

    Listing Information:

    VIN: WDDNG86X18A161795
    Stock: RDA1444
    Certified Pre-Owned: No
    Listed since: 01-11-2025

  • $9,999
    fair price
    $266 above market
    • 116,850 miles
    • No accidents, 5 owners, corporate fleet vehicle
    • 14 City / 20 Hwy MPG
    • Drive 1 Auto Sales (141 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wake Forest, NC / 141 miles away from Chesapeake, VA

    This Luxury was driven only 7,303 miles/year, currently at 116,850 miles plus the automatic transmission makes driving easier in stop-and-go traffic a...

    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:

    16 Combined MPG (14 City/20 Highway)

    Listing Information:

    VIN: WDDNG86X48A162469
    Stock: 162469
    Certified Pre-Owned: No
    Listed since: 12-10-2024

  • $10,488
    fair price
    $888 above market
    • 128,622 miles
    • No accidents, 2 owners, personal use
    • 14 City / 20 Hwy MPG
    • Rolls-Royce Motor Cars Raleigh (144 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    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:

    16 Combined MPG (14 City/20 Highway)

    Listing Information:

    VIN: WDDNG86X98A183253
    Stock: R5146B
    Certified Pre-Owned: No
    Listed since: 05-21-2025

  • $12,500
    fair price
    $297 above market
    • 107,319 miles
    • No accidents, 2 owners, personal use
    • 15 City / 25 Hwy MPG
    • A&A Auto Sales (158 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Fuquay Varina, NC / 158 miles away from Chesapeake, VA

    CLEAN CARFAX !!!NO ACCIDENTS2 OWNER !!!LOCAL VEHICLEGOOD MAINTENANCE HISTORY!15 SERVICE HISTORY RECORDS!! See Carfax for details.INCLUDES A 90 DAY, 50...

    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 (15 City/25 Highway)

    Listing Information:

    VIN: WDDNG7DB5CA461205
    Stock: 11430
    Certified Pre-Owned: No
    Listed since: 05-13-2025

  • $10,990
    fair price
    $931 above market
    • 104,511 miles
    • No accidents, 1 owner, personal use only
    • 14 City / 20 Hwy MPG
    • 4x4 Auto Group (160 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Vienna, VA / 160 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:

    16 Combined MPG (14 City/20 Highway)

    Listing Information:

    VIN: WDDNG86X18A200868
    Stock: 00119
    Certified Pre-Owned: No
    Listed since: 01-19-2025

Showing 43 - 63 out of 475 listings

Consumer Reviews for the Mercedes-Benz S-Class

Read recent reviews for the Mercedes-Benz S-Class
Overall Consumer Rating
4.6 out of 5 stars32 Reviews
Write a vehicle reviewSee all 32 reviews
  • 5 star
    (81%)
  • 4 star
    (9%)
  • 3 star
    (3%)
  • 2 star
    (6%)
  • 1 star
    (0%)
4 out of 5 stars

Love what you drive...and I love the S550

minh tran, 05/18/2016
2010 Mercedes-Benz S-Class S550 4dr Sedan (5.5L 8cyl 7A)
For the 2010, everything you need (and then some) is included in this car. Engine is strong and accelerating with ease. The ride is quiet and smooth. Sport mode brings the car back alive with both acceleration and handling. Only downside for me is bluetooth: voice only and no music streaming Updates: i got the car 2.5 years ago with 50k miles and it is now 127k miles... still run … smooth as the day I got it. Cost abit for maint though. Her’s what I spent $3400 for 4 shocks...all went dead around 105k miles and the car was sagging 2 set of tires aound $2500 total Oild change every 7k miles with full synthentic ( $115x 10 = $1,150). I bought the oil and filter and have a mechanic close to where I live change and top off fluids and rotate tires 2 alignments (one paid for by Mercedes, the other one is $99) so just say $100 since labor only nonparts A brandnew windshield - $100 deductible Water pump and belt = $600 So all maint is about $8,000 not too bad for a S550 Now this the part that it will shock you Fuel/gas = almost $15,000 but I did drive over 75,000 miles so about 30,800 miles a year... It’s a nice car to drive but as you can see, cost about $23,000 to maintain it if you drive as much as I do. Hope this realistic review helps ya ... Gas is about
Report abuse

Used 2009 Mercedes-Benz S-Class in Chesapeake, VA Values

Estimated values
2009 Mercedes-Benz S-Class S63 AMG 4dr Sedan (6.2L 8cyl 7A) with no options
ConditionTrade-InPrivate PartyDealer Retail
Outstanding$11,005$13,832$15,584
Clean$10,364$12,915$14,433
Average$9,295$11,388$12,514
Rough$7,906$9,402$10,020

The average list price of a used 2009 Mercedes-Benz S-Class in Chesapeake, Virginia is $15,575. The average mileage on a used Mercedes-Benz S-Class 2009 for sale in Chesapeake, Virginia is 99,053. Based on the average mileage of 99,053 for used 2009 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 2009 in Chesapeake, Virginia to be $9,295.

Filters
Skip to Results

Applied Filters4Active

Select Buying Experience

Location

Search radius200 miles
Search radius

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

Listing Details


* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.