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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94 listings
- 32,296 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KY to MA*
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Located in Louisville, KY / 711 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: 5TDAAAB57RS003875
Stock: 27393636
Certified Pre-Owned: No- Price Drop$50,590fair price$159 below market
- 40,412 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Atlanta, GA / 852 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: Yes
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB51RS019151
Stock: 2003856261
Certified Pre-Owned: No
Listed since: 07-12-2025 - $50,998good price$1,417 below market
- 15,597 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to MA*
Close
Located in Sanford, FL / 1,046 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: 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: Yes
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB51RS011728
Stock: 27241833
Certified Pre-Owned: No - $44,995fair price$577 above market
- 32,105 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Mangino Buick GMC (47 mi away)
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Located in Ballston Spa, NY / 47 miles away from Pittsfield, MA
3.33 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, Auto High-beam He...
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: 5TDAAAB53RS011875
Stock: 144625A
Certified Pre-Owned: No
Listed since: 07-12-2025 - Price Drop
- 3,712 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from OH to MA*
Close
Located in Columbus, OH / 535 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB53RS054578
Stock: 27668254
Certified Pre-Owned: No - 11,485 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Richmond, VA / 404 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB54RS015790
Stock: 2003927347
Certified Pre-Owned: No
Listed since: 07-26-2025- 552 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 28 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: 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: 5TDAAAA55RS018134
Stock: 2003904534
Certified Pre-Owned: No
Listed since: 07-22-2025- 64 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to MA*
Close
Located in Fredericksburg, VA / 367 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB53SS084895
Stock: 27575195
Certified Pre-Owned: No- New Listing
- 1,775 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to MA*
Close
Located in San Diego, CA / 2,463 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: No
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA52SS021675
Stock: 26887372
Certified Pre-Owned: No - New Listing
- 3,519 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to MA*
Close
Located in Puyallup, WA / 2,385 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: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB52SS080353
Stock: 27470534
Certified Pre-Owned: No - 8,845 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to MA*
Close
Located in Puyallup, WA / 2,385 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB51RS019327
Stock: 27434636
Certified Pre-Owned: No- Price Drop$47,590fair price$892 above market
- 11,387 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 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: 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: 5TDAAAB59RS044850
Stock: 2003822003
Certified Pre-Owned: No
Listed since: 07-02-2025 - Price Drop$47,990fair price$1,076 above market
- 12,275 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 1,127 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA57RS007457
Stock: 2003826101
Certified Pre-Owned: No
Listed since: 07-02-2025 - New Listing
- 11,247 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NC to MA*
Close
Located in Raleigh, NC / 540 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: No
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA58RS016958
Stock: 27574977
Certified Pre-Owned: No - 15,351 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to MA*
Close
Located in Roanoke, VA / 503 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: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB55RS036504
Stock: 27037244
Certified Pre-Owned: No- New Listing
- 16,521 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to MA*
Close
Located in Santa Rosa, CA / 2,579 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: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB54RS018222
Stock: 27185852
Certified Pre-Owned: No - New Listing$48,998fair price$86 above market
- 35,477 miles
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NC to MA*
Close
Located in Charlotte, NC / 644 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 Unavailable.
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB53RS013559
Stock: 27724371
Certified Pre-Owned: No - New Listing
- 19,447 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to MA*
Close
Located in Palm Desert, CA / 2,392 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: No
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA51RS009415
Stock: 26847811
Certified Pre-Owned: No - Price Drop$47,990fair price$561 above market
- 18,053 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 1,127 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA53RS004281
Stock: 2003786492
Certified Pre-Owned: No
Listed since: 06-10-2025 - Price Drop$45,991fair price$179 below market
- 54,929 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Freehold, NJ / 160 miles away from Pittsfield, MA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wh...
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB51RS010482
Stock: S3044525A
Certified Pre-Owned: No - New Listing
- 29,287 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 27 Hwy MPG
- Diamond Chevrolet Buick GMC (74 mi away)
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Located in Auburn, MA / 74 miles away from Pittsfield, MA
At Diamond Auto Group we want you to know that all our vehicles are priced at a competitive value position to the market. We use an independent 3rd pa...
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: 5TDAAAB59RS012870
Stock: SI25139A
Certified Pre-Owned: No
Listed since: 07-27-2025
Showing 64 - 84 out of 94 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.