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90 listings
  • $47,274
    great price
    $4,315 below market
    • 21,295 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 26 Hwy MPG
    • Lia Toyota of Colonie (38 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Schenectady, NY / 38 miles away from Pittsfield, MA

    CARFAX One-Owner. Certified. Storm Cloud 2024 Toyota Grand Highlander Limited AWD 8-Speed Automatic 2.4L 4-Cylinder 2024 Toyota Grand Highlander Limit...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB5XRS004017
    Stock: RS004017T
    Certified Pre-Owned: Yes
    Listed since: 06-06-2025

  • $52,995
    great price
    $2,763 below market
    • 11,590 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Greentree Toyota (72 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Danbury, CT / 72 miles away from Pittsfield, MA

    Certified. CARFAX One-Owner. 2024 Toyota Grand Highlander Limited AWD20" Aluminum Alloy Wheels, ABS brakes, Active Cruise Control, Alloy wheels, Elec...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB54RS053617
    Stock: U21950A
    Certified Pre-Owned: Yes
    Listed since: 10-22-2024

  • $55,995
    good price
    $1,709 below market
    • 1,850 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Toyota of Keene (60 mi away)
    • AWD/4WD
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Swanzey, NH / 60 miles away from Pittsfield, MA

    Certified. Clean CARFAX. 2025 Toyota Grand Highlander Platinum AWD 8-Speed Automatic 2.4L 4-CylinderABS brakes, Active Cruise Control, Alloy wheels,...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB58SS075965
    Stock: 350392A
    Certified Pre-Owned: Yes
    Listed since: 05-19-2025

  • $46,898
    good price
    $1,070 below market
    • 21,575 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • Faith's Toyota (62 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Westminster, VT / 62 miles away from Pittsfield, MA

    *ALL DISCOUNTED PRICING REFLECTS FINANCING WITH TFS AT STANDARD RATES.Stop by Faith's Ford Toyota Located at 6896 US-5, Westminster, VT. We have the...

    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDAAAB5XRS040743
    Stock: T15694A
    Certified Pre-Owned: Yes
    Listed since: 06-20-2025

  • $46,000
    fair price
    $375 below market
    • 24,818 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 21 City / 27 Hwy MPG
    • Westboro Toyota (83 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Westborough, MA / 83 miles away from Pittsfield, MA

    At Westboro Toyota we want you to know that all our vehicles are priced at a competitive value position to the market. We use an independent 3rd party...

    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDAAAB55RS062035
    Stock: PH77251
    Certified Pre-Owned: No
    Listed since: 04-23-2025

  • New Listing
    $51,098
    fair price
    $309 above market
    • 7,408 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Rensselaer Honda (28 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Troy, NY / 28 miles away from Pittsfield, MA

    **Recent Arrival** **Odometer is 11893 miles below market average** Experience unparalleled comfort, capability, and cutting-edge technology with the ...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB55RS055635
    Stock: 250924A
    Certified Pre-Owned: No
    Listed since: 07-22-2025

  • $46,500
    fair price
    $1,078 above market
    • 18,590 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • Westboro Toyota (83 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Westborough, MA / 83 miles away from Pittsfield, MA

    At Westboro Toyota we want you to know that all our vehicles are priced at a competitive value position to the market. We use an independent 3rd party...

    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDAAAB53RS050126
    Stock: P77369
    Certified Pre-Owned: No
    Listed since: 04-21-2025

  • Price Drop
    $47,498
    fair price
    $226 above market
    • 28,854 miles
    • No accidents, 1 owner, personal use only
    • 8 Seats, 20 City / 26 Hwy MPG
    • Herb Chambers BMW of Sudbury (95 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Sudbury, MA / 95 miles away from Pittsfield, MA

    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:

    22 Combined MPG (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB56RS006735
    Stock: L34055A
    Certified Pre-Owned: No
    Listed since: 07-02-2025

    • 38,900 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Faith's Toyota (62 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Westminster, VT / 62 miles away from Pittsfield, MA

    *ALL DISCOUNTED PRICING REFLECTS FINANCING WITH TFS AT STANDARD RATES.Stop by Faith's Ford Toyota Located at 6896 US-5, Westminster, VT. We have the...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB57RS012429
    Stock: T15728A
    Certified Pre-Owned: Yes
    Listed since: 06-26-2025

  • New Listing
    Stock photo**
    $49,641
    fair price
    $168 above market
    • 17,411 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • McGee Toyota of Claremont (77 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Claremont, NH / 77 miles away from Pittsfield, MA

    Recent Arrival!20" Aluminum Alloy Wheels, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated d...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB52RS007607
    Stock: T25032
    Certified Pre-Owned: No
    Listed since: 07-18-2025

  • Stock photo**
    • 18,757 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 20 City / 26 Hwy MPG
    • Middletown Toyota (68 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Middletown, CT / 68 miles away from Pittsfield, MA

    Recent Arrival! New Price! Certified. CARFAX One-Owner. Clean CARFAX.2024 Toyota Grand Highlander Limited AWD 8-Speed Automatic 2.4L 4-CylinderFre...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB5XRS010884
    Stock: BL06439U
    Certified Pre-Owned: Yes
    Listed since: 06-30-2025

  • New Listing
    • 505 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • CarMax Hartford (55 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Hartford, CT / 55 miles away from Pittsfield, MA

    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDAAAB59RS068386
    Stock: 27030908
    Certified Pre-Owned: No

  • New Listing
    • 7,026 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 27 Hwy MPG
    • CarMax Hartford (55 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Hartford, CT / 55 miles away from Pittsfield, MA

    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDAAAB53RS040647
    Stock: 27653777
    Certified Pre-Owned: No

    • 21,675 miles
    • No accidents, 1 owner, personal use
    • 7 Seats, 21 City / 27 Hwy MPG
    • Colonial Chevrolet (94 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Acton, MA / 94 miles away from Pittsfield, MA

    Highlights of this 2024 Toyota Grand Highlander include: Serviced here, Non-Smoker vehicle, Very Nice, CARFAX 1-Owner. JUST REPRICED FROM $47,988, EPA...

    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:

    23 Combined MPG (21 City/27 Highway)

    Listing Information:

    VIN: 5TDAAAB54RS036851
    Stock: C25109A
    Certified Pre-Owned: No
    Listed since: 04-04-2025

  • $45,990
    great price
    $7,595 below market
    • 18,783 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 20 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Cleveland, OH / 439 miles away from Pittsfield, MA

    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: 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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB57RS063784
    Stock: 2003627729
    Certified Pre-Owned: No
    Listed since: 04-09-2025

  • $49,999
    good price
    $3,064 below market
    • 2,285 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Farmington Hills, MI / 517 miles away from Pittsfield, MA

    Low Mileage

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB56RS059628
    Stock: RS059628P
    Certified Pre-Owned: No

    • 18,985 miles
    • No accidents, 1 owner, rental vehicle
    • 7 Seats, 20 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Dallas, TX / 1,443 miles away from Pittsfield, MA

    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: 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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB54RS060468
    Stock: 2003754664
    Certified Pre-Owned: No
    Listed since: 05-21-2025

  • Price Drop
    $49,953
    great price
    $3,186 below market
    • 13,521 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Harr Toyota (75 mi away)
    • AWD/4WD
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Worcester, MA / 75 miles away from Pittsfield, MA

    PERFECT PRICE!, TOYOTA CERTIFIED, REMAINDER OF FACRORY WARRANTY, INCLUDES WARRANTY, ONE OWNER, CLEAN VEHICLE HISTORY, SERVICE RECORDS AVAILABLE, RECEN...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB5XRS031931
    Stock: M3383A
    Certified Pre-Owned: Yes
    Listed since: 06-01-2025

  • $47,574
    great price
    $3,390 below market
    • 25,760 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Casey Chrysler Dodge Jeep Ram of Springfield (70 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Springfield, VT / 70 miles away from Pittsfield, MA

    Midnight Black Metallic 2024 Toyota Grand Highlander Limited AWD 8-Speed Automatic 2.4L 4-Cylinder 20" Aluminum Alloy Wheels, ABS brakes, Active Cruis...

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB51RS049248
    Stock: SP1361A
    Certified Pre-Owned: No
    Listed since: 07-10-2025

    • 26,496 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 21 City / 28 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Grapevine, TX / 1,451 miles away from Pittsfield, MA

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free L...

    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/28 Highway)

    Listing Information:

    VIN: 5TDAAAA55RS002886
    Stock: RS002886A
    Certified Pre-Owned: No

  • Price Drop
    $45,590
    good price
    $2,065 below market
    • 40,028 miles
    • No accidents, 1 owner, personal use only
    • 7 Seats, 20 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Indianapolis, IN / 696 miles away from Pittsfield, MA

    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 (20 City/26 Highway)

    Listing Information:

    VIN: 5TDAAAB58RS032687
    Stock: 2003718167
    Certified Pre-Owned: No
    Listed since: 05-12-2025

Showing 1 - 21 out of 90 listings
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.