Used Toyota Grand Highlander for Sale in Pittsfield, MA
Shop for a luxurious Toyota Grand Highlander in the county seat of Berkshire County, Massachusetts
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88 listings
- $45,991great price$6,066 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*
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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 - Price Drop$46,698good price$1,595 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)
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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 - $52,995good price$2,897 below market
- 11,590 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Greentree Toyota (72 mi away)
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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 - Price Drop$47,698fair price$86 below market
- 38,900 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Faith's Toyota (62 mi away)
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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 - $48,163good price$1,411 below market
- 17,431 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- McGee Toyota of Claremont (77 mi away)
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Located in Claremont, NH / 77 miles away from Pittsfield, MA
4-wheel alignment, 4-wheel disc brake caliper service!20" Aluminum Alloy Wheels, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability...
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 - $51,098fair price$219 above market
- 7,408 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Rensselaer Honda (28 mi away)
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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 - $46,000fair price$820 below market
- 24,903 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 27 Hwy MPG
- Westboro Toyota (83 mi away)
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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 - $46,998fair price$491 below 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)
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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 - $46,500fair price$742 above market
- 18,590 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Westboro Toyota (83 mi away)
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 - New Listing$44,995fair price$108 above market
- 38,419 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 27 Hwy MPG
- Lia Honda Albany (33 mi away)
- Home delivery*
Close
Located in Albany, NY / 33 miles away from Pittsfield, MA
Storm Cloud 2024 Toyota Grand Highlander XLE AWD 8-Speed Automatic 2.4L 4-Cylinder ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stabili...
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: 5TDAAAB55RS043047
Stock: RS043047T
Certified Pre-Owned: No
Listed since: 07-30-2025 - $46,995fair price$1,354 above market
- 21,675 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 27 Hwy MPG
- Colonial Chevrolet (94 mi away)
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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 - $50,497fair price$178 above market
- 18,757 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Middletown Toyota (68 mi away)
Close
Located in Middletown, CT / 68 miles away from Pittsfield, MA
Certified. CARFAX One-Owner. Clean CARFAX.2024 Toyota Grand Highlander Limited AWD 8-Speed Automatic 2.4L 4-CylinderFresh oil change, 160 point To...
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 - 505 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax Hartford (55 mi away)
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- 7,028 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax East Haven (83 mi away)
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Located in East Haven, CT / 83 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- New Listing
- 10,718 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Herb Chambers Toyota of Auburn (74 mi away)
Close
Located in Auburn, MA / 74 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: 5TDAAAB57RS048993
Stock: A286022A
Certified Pre-Owned: No
Listed since: 07-30-2025 - 8,932 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- MacMulkin Chevrolet (94 mi away)
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Located in Nashua, NH / 94 miles away from Pittsfield, MA
2024 Toyota Grand Highlander Clean CARFAX.
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: 5TDAAAB57RS058634
Stock: T28078A
Certified Pre-Owned: No
Listed since: 07-21-2025- New Listing
- 41,728 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- State Motors Lincoln (100 mi away)
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Located in Manchester, NH / 100 miles away from Pittsfield, MA
This Toyota Grand Highlander delivers a Intercooled Turbo Regular Unleaded I-4 2.4 L/146 engine powering this Automatic transmission. Window Grid Dive...
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: 5TDAAAB58RS016361
Stock: 24L219B
Certified Pre-Owned: No
Listed since: 08-02-2025 - $45,590great price$7,615 below market
- 18,783 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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 - Price Drop$49,749good price$3,139 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*
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 - Price Drop$44,990great price$4,102 below market
- 13,886 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Sacramento, CA / 2,513 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA55RS017372
Stock: 2003912080
Certified Pre-Owned: No
Listed since: 07-29-2025 - $46,990great price
- 18,985 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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
Showing 1 - 21 out of 88 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.