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144 listings
  • $87,944
    great price
    $17,412 below market
    • 17,612 miles
    • No accidents, 2 owners, personal use only
    • 16 City / 25 Hwy MPG
    • Land Rover Albany (35 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Albany, NY / 35 miles away from Bennington, VT

    Land Rover Albany is proud to present this Pre Owned 2023 Mercedes-Benz S580 4Matic Sedan. This vehicle features:Cirrus Silver Metallic ExteriorMacchi...

    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: W1K6G7GBXPA195279
    Stock: L1902A
    Certified Pre-Owned: No
    Listed since: 06-14-2025

  • New Listing
    • 4,327 miles
    • No accidents, 1 owner, personal use only
    • 16 mi est. electric range
    • 15 City / 23 Hwy MPG
    • Mercedes-Benz of Sudbury (98 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Sudbury, MA / 98 miles away from Bennington, VT

    INSPECTION COMPLETED Every Herb Chambers Certified pre-owned vehicle receives a complete multi-point inspection by factory trained technicians who ins...

    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: W1K6G8CB4SA312844
    Stock: M72832A
    Certified Pre-Owned: Yes
    Listed since: 06-26-2025

  • $25,995
    great price
    $5,398 below market
    • 97,550 miles
    • 1 accident, 3 owners, personal use only
    • 15 City / 23 Hwy MPG
    • A Better Way Wholesale Autos (95 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Naugatuck, CT / 95 miles away from Bennington, VT

    - Experience exhilarating performance with a 5.5L Twin Turbo V8 engine delivering 577hp and 664 lb-ft of torque. - Indulge in luxury with a meticulou...

    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: WDDUG7JB2EA048337
    Stock: 48337N
    Certified Pre-Owned: No

  • $125,680
    fair price
    $4,787 below market
    • 6,779 miles
    • No accidents, 1 owner, personal use only
    • 17 City / 25 Hwy MPG
    • Mercedes-Benz of Wappingers Falls (97 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wappingers Falls, NY / 97 miles away from Bennington, VT

    CARFAX One-Owner. Clean CARFAX. Black 2025 Mercedes-Benz S-Class S 580 4MATIC® 4D Sedan 4MATIC® 4.0L V8 4.0L V8, 4MATIC®, Black Leather, ABS brakes, A...

    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: W1K6G7GB9SA313735
    Stock: L0883L
    Certified Pre-Owned: No
    Listed since: 11-22-2024

  • New Listing
    • 11,987 miles
    • No accidents, 1 owner, personal use only
    • Herb Chambers Alfa Romeo of Boston (99 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wayland, MA / 99 miles away from Bennington, VT

    INSPECTION COMPLETED Every Herb Chambers Certified pre-owned vehicle receives a complete multi-point inspection by factory trained technicians who ins...

    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: W1K6G8CB6RA273135
    Stock: NB2236
    Certified Pre-Owned: No
    Listed since: 05-15-2025

  • New Listing
    $23,490
    great price
    $9,579 below market
    • 72,880 miles
    • 3 accidents, 3 owners, personal use
    • 17 City / 25 Hwy MPG
    • Faris Auto Mall (83 mi away)
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Upgraded Headlights
    Close

    Located in Manchester, CT / 83 miles away from Bennington, VT

    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: WDDUG8CB3EA009016
    Stock: NV11384
    Certified Pre-Owned: No

  • $64,995
    good price
    $2,970 below market
    • 31,741 miles
    • No accidents, 1 owner, personal use
    • 16 City / 25 Hwy MPG
    • A Better Way Wholesale Autos (95 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Naugatuck, CT / 95 miles away from Bennington, VT

    - Experience unparalleled luxury with the 2022 Mercedes-Benz S-Class S 580 4MATIC, boasting a low mileage of just 31,741 miles. - Stand out with its ...

    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: W1K6G7GB1NA085850
    Stock: 85850N
    Certified Pre-Owned: No

  • $25,990
    great price
    $3,545 below market
    • 83,844 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 16 City / 25 Hwy MPG
    • Faris Auto Mall (83 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Manchester, CT / 83 miles away from Bennington, VT

    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 (16 City/25 Highway)

    Listing Information:

    VIN: WDDUG8FB2HA333929
    Stock: NV11496
    Certified Pre-Owned: No

  • Price Drop
    $59,899
    fair price
    $1,566 below market
    • 60,479 miles
    • No accidents, 2 owners, personal use only
    • 17 City / 25 Hwy MPG
    • Toyota of Nashua (89 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Nashua, NH / 89 miles away from Bennington, VT

    Recent Arrival! Toyota of Nashua is proud to present this McGovern Certified... Selenite Gray Metallic 2021 Mercedes-Benz S-Class S 580 4MATIC® 4.0L V...

    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: W1K6G7GB4MA019582
    Stock: N24533T
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • $19,799
    fair price
    $193 above market
    • 129,216 miles
    • No accidents, 2 owners, personal use
    • 16 City / 26 Hwy MPG
    • Choice Motor Car (86 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Plainville, CT / 86 miles away from Bennington, VT

    Buy it with cash or finance with $2100 down and low weekly payments deducted straight from your checking or savings. Have good credit? We work with se...

    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: WDDUG8FB2FA158210
    Stock: 158210
    Certified Pre-Owned: No
    Listed since: 11-05-2024

  • Stock photo**
    $129,564
    fair price
    $1,137 above market
    • 4,172 miles
    • No accidents, 1 owner, personal use only
    • 17 City / 25 Hwy MPG
    • Mercedes-Benz of Wappingers Falls (97 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wappingers Falls, NY / 97 miles away from Bennington, VT

    CARFAX One-Owner. Nautical Blue Metallic 2025 Mercedes-Benz S-Class S 580 4MATIC® 4D Sedan 4MATIC® 4.0L V8 18/27 City/Highway MPG Odometer is 1255 mil...

    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: W1K6G7GB3SA319904
    Stock: L0894L
    Certified Pre-Owned: No
    Listed since: 11-15-2024

  • Price Drop
    $27,995
    fair price
    $392 below market
    • 45,894 miles
    • 1 accident, 1 owner, personal use only
    • 16 City / 26 Hwy MPG
    • A Better Way Wholesale Autos (95 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Naugatuck, CT / 95 miles away from Bennington, VT

    - Experience unparalleled luxury and performance with the 2015 Mercedes-Benz S-Class S 550 4MATIC, boasting a powerful 4.7L Twin Turbo V8 engine. - E...

    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: WDDUG8FB9FA167535
    Stock: 167535N
    Certified Pre-Owned: No

  • $34,998
    fair price
    $1,718 above market
    • 96,987 miles
    • No accidents, 1 owner, personal use
    • 8cyl automatic
    • The Highline Group (95 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Lowell, MA / 95 miles away from Bennington, VT

    CARFAX One-Owner. Clean CARFAX. 2016 Mercedes-Benz S-Class S 550 4MATIC designo Diamond White Metallic 4MATIC 7-Speed Automatic 4.7L V8 BiTurbo 4MATIC...

    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/24 Highway)

    Listing Information:

    VIN: WDDXJ8FB9GA014668
    Stock: 25-411
    Certified Pre-Owned: No

  • $38,990
    fair price
    $1,124 above market
    • 73,439 miles
    • No accidents, 5 owners, personal use
    • 15 City / 23 Hwy MPG
    • Acton Auto Boutique (94 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Acton, MA / 94 miles away from Bennington, VT

    Recently re-acquired. Nicely spec-ed, desirable color, and am absolute beast. Designo Diamond White Paint, Warmth and Comfort Package, Night Vision, ...

    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: WDDUG7JB4FA161496
    Stock: 161496
    Certified Pre-Owned: No
    Listed since: 07-25-2025

  • $14,999
    fair price
    $504 above market
    • 81,226 miles
    • 1 accident, 4 owners, corporate fleet vehicle
    • 15 City / 24 Hwy MPG
    • Choice Motor Car (86 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Plainville, CT / 86 miles away from Bennington, VT

    Absolutely stunning and pristine S550. Super well kept and cared for. Interior looks new from he clean woodgrain, to the flawless seats and trim. It h...

    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:

    18 Combined MPG (15 City/24 Highway)

    Listing Information:

    VIN: WDDNG9EB8CA429701
    Stock: 429701
    Certified Pre-Owned: No
    Listed since: 03-24-2025

    • 9,725 miles
    • No accidents, 1 owner, personal use only
    • The Highline Group (95 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Lowell, MA / 95 miles away from Bennington, VT

    CARFAX One-Owner. Clean CARFAX. 2024 Mercedes-Benz S-Class S 580e 4MATIC Obsidian Black Metallic 4MATIC 9-Speed Automatic I6 4MATIC, Exclusive Sienna ...

    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:

    Listing Information:

    VIN: W1K6G6KB0RA264159
    Stock: 25-574
    Certified Pre-Owned: No

    • 141,430 miles
    • No accidents, 3 owners, personal use
    • 14 City / 21 Hwy MPG
    • The Highline Group (95 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Lowell, MA / 95 miles away from Bennington, VT

    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:

    17 Combined MPG (14 City/21 Highway)

    Listing Information:

    VIN: WDDNG8GB3AA321684
    Stock: 25-459
    Certified Pre-Owned: No

    • 34,546 miles
    • No accidents, 2 owners, personal use
    • 20 City / 29 Hwy MPG
    • Mercedes-Benz of Wappingers Falls (97 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wappingers Falls, NY / 97 miles away from Bennington, VT

    Recent Arrival! designo Diamond White Metallic 2021 Mercedes-Benz S-Class S 500 4MATIC® 4D Sedan 4MATIC® 3.0L V6 Turbocharged 20/29 City/Highway MPG 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: W1K6G6DB6MA032526
    Stock: U4456P
    Certified Pre-Owned: Yes
    Listed since: 07-05-2025

  • New Listing
    • 59,229 miles
    • No accidents, 2 owners, personal use only
    • 17 City / 27 Hwy MPG
    • Herb Chambers Alfa Romeo (86 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Millbury, MA / 86 miles away from Bennington, VT

    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: WDDUG8GB6JA399386
    Stock: NWF170081LB
    Certified Pre-Owned: No
    Listed since: 07-16-2025

    • 116,619 miles
    • No accidents, 4 owners, corporate fleet vehicle
    • 14 City / 20 Hwy MPG
    • Choice Motor Car (86 mi away)
    • AWD/4WD
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    • Upgraded Headlights
    Close

    Located in Plainville, CT / 86 miles away from Bennington, VT

    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: WDBNG84J85A451387
    Stock: 451387
    Certified Pre-Owned: No
    Listed since: 07-17-2025

  • New Listing
    $29,790
    good price
    $2,499 below market
    • 72,000 miles
    • No accidents, 5 owners, corporate fleet vehicle
    • 16 City / 25 Hwy MPG
    • Faris Auto Mall (83 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Manchester, CT / 83 miles away from Bennington, VT

    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 (16 City/25 Highway)

    Listing Information:

    VIN: WDDUG8FB9HA311751
    Stock: NV11420
    Certified Pre-Owned: No

Showing 1 - 21 out of 144 listings
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