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
- $54,991fair price$186 above market
- 6,765 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Blasius Cadillac (65 mi away)
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Located in Waterbury, CT / 65 miles away from Pittsfield, MA
Blueprint 2025 Toyota Grand Highlander Limited AWD 8-Speed Automatic 2.4L 4-Cylinder HEATED LEATHER SEATS, PANORAMIC ROOF, ALL WHEEL DRIVE, CLEAN VEHI...
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: 5TDAAAB54SS073310
Stock: 073310
Certified Pre-Owned: No
Listed since: 06-12-2025 - Price Drop$45,590fair price$1,114 above market
- 13,025 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Phoenix, AZ / 2,179 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: 5TDAAAA54RS011417
Stock: 2003837420
Certified Pre-Owned: No
Listed since: 07-02-2025 - New Listing$48,990fair price
- 8,234 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in San Antonio, TX / 1,664 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: 5TDAAAA50RS018459
Stock: 2003919294
Certified Pre-Owned: No
Listed since: 07-28-2025 - Price Drop$48,977fair price$412 above market
- 8,454 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Imperial Toyota (93 mi away)
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Located in Milford, MA / 93 miles away from Pittsfield, MA
Navigation System, Blind Spot Monitor, Lane Keeping Assistance, Apple CarPlay / Android Auto, Adaptive Cruise Control, Cross Traffic Alert, Power Seat...
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: 5TDAAAB53RS059263
Stock: TP5720
Certified Pre-Owned: Yes
Listed since: 06-07-2025 - Price Drop
- 11,824 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Seattle, WA / 2,382 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB57RS041526
Stock: S041526MH
Certified Pre-Owned: No - $47,995fair price$48 above market
- 11,981 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in West Allis, WI / 750 miles away from Pittsfield, MA
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless S...
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: 5TDAAAB5XRS061480
Stock: G92731
Certified Pre-Owned: No - New Listing$45,998fair price$962 below market
- 23,659 miles
- 8 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from OR to MA*
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Located in Beaverton, OR / 2,433 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB53RS030555
Stock: 27076525
Certified Pre-Owned: No - New Listing$52,998fair price$629 below market
- 17,846 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from SC to MA*
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Located in Greenville, SC / 719 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: 5TDAAAB52RS058900
Stock: 27290831
Certified Pre-Owned: No - New Listing$46,998fair price$941 above market
- 18,842 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from MD to MA*
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Located in Salisbury, MD / 306 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB59RS042967
Stock: 27103006
Certified Pre-Owned: No - $52,998fair price$369 above market
- 19,797 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to MA*
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Located in Reno, NV / 2,405 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: 5TDAAAB58RS001441
Stock: 26859399
Certified Pre-Owned: No - Price Drop$45,590fair price$296 above market
- 22,697 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Phoenix, AZ / 2,179 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: 5TDAAAB53RS042771
Stock: 2003865076
Certified Pre-Owned: No
Listed since: 07-21-2025 - New Listing
- 21,213 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to MA*
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Located in Norcross, GA / 834 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: 5TDAAAA54RS011885
Stock: 27331826
Certified Pre-Owned: No - New Listing$53,995fair price$788 above market
- 26,778 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Acura of Milford (84 mi away)
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Located in Milford, CT / 84 miles away from Pittsfield, MA
Toyota Certified, Excellent Condition, CARFAX 1-Owner. FUEL EFFICIENT 26 MPG Hwy/20 MPG City! Heated Leather Seats, Moonroof, Navigation, Third Row 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB5XRS017348
Stock: 56859
Certified Pre-Owned: No
Listed since: 05-10-2025 - New Listing$46,998fair price$763 above market
- 22,105 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to MA*
Close
Located in Roseville, CA / 2,497 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB58RS023262
Stock: 27421106
Certified Pre-Owned: No - $53,991fair price$687 above market
- 21,795 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Colonial Toyota (85 mi away)
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Located in Milford, CT / 85 miles away from Pittsfield, MA
Shop in comfort in our huge heated and air conditioned showroom Call today (2**) 8**-7***.Certified.Midnight Black Metallic 2024 Toyota Grand Highland...
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: 5TDAAAB56RS013541
Stock: RS013541
Certified Pre-Owned: Yes
Listed since: 05-13-2025 - Price Drop$46,998fair price$605 above market
- 25,019 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NJ to MA*
Close
Located in Mays Landing, NJ / 220 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB57RS022975
Stock: 27572862
Certified Pre-Owned: No - $39,805fair price$1,041 below market
- 55,379 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Phoenix, AZ / 2,178 miles away from Pittsfield, MA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Navigation System,S...
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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA57RS013761
Stock: RS013761T
Certified Pre-Owned: No - New Listing$43,998fair price$696 below market
- 29,165 miles
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to MA*
Close
Located in Richmond, VA / 403 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB53RS025016
Stock: 27677812
Certified Pre-Owned: No - $51,988fair price$32 below market
- 32,644 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Jake Sweeney Express (In-stock online)
- Home delivery*
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Located in Cincinnati, OH / 625 miles away from Pittsfield, MA
Jake Sweeney Is Here to Help! If you are in need of a new or used vehicle, we are offering you the ability to shop online and have your vehicle delive...
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: 5TDAAAB57RS000460
Stock: G18799
Certified Pre-Owned: No
Listed since: 07-24-2025 - New Listing$51,998fair price$895 above market
- 33,417 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to MA*
Close
Located in Modesto, CA / 2,511 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: 5TDAAAB56RS003740
Stock: 27458282
Certified Pre-Owned: No - $43,982fair price$165 above market
- 56,085 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 27 Hwy MPG
- Westbrook Toyota (91 mi away)
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Located in Westbrook, CT / 91 miles away from Pittsfield, MA
CARFAX 1-Owner, Toyota Certified, Superb Condition. EPA 27 MPG Hwy/21 MPG City! Nav System, Third Row Seat, Heated Seats, Back-Up Camera, Rear Air, Po...
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: 5TDAAAB5XRS025465
Stock: 56847
Certified Pre-Owned: Yes
Listed since: 07-01-2025
Showing 43 - 63 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.