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1,527 listings
- $31,000great price$4,827 below market
- 44,958 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- AutoMax PreOwned Framingham (93 mi away)
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Located in Framingham, MA / 93 miles away from Pittsfield, MA
8-Passenger AWD - Magnetic Gray exterior on Black interior with Apple CarPlay / Android Auto, Backup Camera, Steering Wheel Mounted Media Controls, Ac...
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: Yes
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH1PS039708
Stock: 039708
Certified Pre-Owned: No
Listed since: 04-24-2025 - New Listing$13,935great price$8,842 below market
- 59,793 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- McGee Toyota of Claremont (76 mi away)
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Located in Claremont, NH / 76 miles away from Pittsfield, MA
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 (18 City/24 Highway)
Listing Information:
VIN: 5TDJKRFHXGS353739
Stock: TR575140A
Certified Pre-Owned: No
Listed since: 08-27-2025 - $13,495great price$3,190 below market
- 99,437 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (66 mi away)
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Located in Naugatuck, CT / 66 miles away from Pittsfield, MA
- Experience the perfect blend of power and efficiency with a robust 3.5L V6 engine delivering 270hp. - Luxurious leather interior ensures comfort an...
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 (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EH0CS160389
Stock: 160389N
Certified Pre-Owned: No - $14,995great price$2,128 below market
- 131,332 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- A Better Way Wholesale Autos (66 mi away)
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Located in Naugatuck, CT / 66 miles away from Pittsfield, MA
- **Proven Reliability**: Award-winning 2016 Toyota Highlander XLE with a 3.5L V6 engine, recognized by Edmunds, J.D. Power, and Kelley Blue Book for ...
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 (18 City/24 Highway)
Listing Information:
VIN: 5TDJKRFH0GS240351
Stock: 240351N
Certified Pre-Owned: No - Price Drop$33,950great price$3,177 below market
- 72,287 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- McGee Toyota of Claremont (76 mi away)
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Located in Claremont, NH / 76 miles away from Pittsfield, MA
New front and rear brake pads and rotors, 4-wheel alignment, new front struts!AWD, Alloy wheels, Apple CarPlay/Android Auto, Auto High-beam Headlights...
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 (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH3NS181696
Stock: 250349A
Certified Pre-Owned: Yes
Listed since: 08-02-2025 - $37,886great price$3,173 below market
- 30,662 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Hurd Auto Mall (99 mi away)
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Located in Johnston, RI / 99 miles away from Pittsfield, MA
Recent Arrival! At Hurd Auto Mall, proudly part of the Balise Family, we have been honored to serve the Rhode Island community for over 85 years, offe...
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: 5TDKDRBH2PS512614
Stock: P42286A
Certified Pre-Owned: No
Listed since: 08-16-2025 - Price Drop$22,976great price$2,002 below market
- 101,226 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Balise Subaru of Hadley (36 mi away)
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Located in Hadley, MA / 36 miles away from Pittsfield, MA
2019 Toyota Highlander in bold Midnight Black Metallic, powered by a strong 3.5L V6 engine paired with an 8-speed automatic transmission with ECT-i. T...
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: 5TDJZRFH6KS567115
Stock: S25015A
Certified Pre-Owned: No
Listed since: 07-12-2025 - $36,999good price$3,870 below market
- 21,460 miles
- No accidents, 2 owners, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Key Chevrolet GMC of Newport (82 mi away)
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Located in Newport, NH / 82 miles away from Pittsfield, MA
2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp Black AWD, ABS brakes, Active Cruise Control, Alloy wheels, Electronic...
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: 5TDKDRBH5PS027576
Stock: E13550A
Certified Pre-Owned: No
Listed since: 06-23-2025 - $21,495great price$2,046 below market
- 97,051 miles
- No accidents, 4 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- A Better Way Wholesale Autos (66 mi away)
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Located in Naugatuck, CT / 66 miles away from Pittsfield, MA
- **Low Mileage & Powerful Performance**: With only 97,051 miles, this 2018 Toyota Highlander SE is equipped with a robust 3.5L V6 engine delivering 2...
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: 5TDJZRFH1JS822414
Stock: 822414N
Certified Pre-Owned: No - Price Drop$33,987great price$2,580 below market
- 28,044 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- New Country Lexus of Latham (34 mi away)
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Located in Latham, NY / 34 miles away from Pittsfield, MA
**CARFAX One-Owner** **PREMIUM AUDIO** **NAVIGATION** **MOONROOF** **HEATED SEATS** Wind Chill Pearl 2022 Toyota Highlander XLE AWD 8-Speed Automatic ...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH2NS238579
Stock: RX25786A
Certified Pre-Owned: No
Listed since: 07-19-2025 - $41,464good price$1,838 below market
- 13,048 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Ingersoll Auto of Danbury (73 mi away)
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Located in Danbury, CT / 73 miles away from Pittsfield, MA
Odometer is 6650 miles below market average! CARFAX One-Owner. Clean CARFAX. Back-Up Camera, 18' Painted Alloy Wheels, 3rd row seats: split-bench, Fro...
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: 5TDKDRBH8RS568057
Stock: A568057
Certified Pre-Owned: No
Listed since: 07-07-2025 - $33,998great price$2,519 below market
- 53,319 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Honda Westborough (82 mi away)
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Located in Westborough, MA / 82 miles away from Pittsfield, MA
Blueprint exterior and Black interior. Heated Seats, Sunroof, 3rd Row Seat, Alloy Wheels, Captains Chairs, Back-Up Camera, Power Liftgate, Serviced 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 (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH4NS246453
Stock: HW54110A
Certified Pre-Owned: No
Listed since: 05-30-2025 - $41,377good price$2,760 below market
- 5,952 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Ingersoll Auto of Danbury (73 mi away)
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Located in Danbury, CT / 73 miles away from Pittsfield, MA
Odometer is 12612 miles below market average! Clean CARFAX. 18' Painted Alloy Wheels, 3rd row seats: split-bench, Front dual zone A/C, Power driver 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH3RS532762
Stock: A532762
Certified Pre-Owned: No
Listed since: 06-20-2025 - $28,925great price$2,733 below market
- 72,047 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Toyota of Wallingford (71 mi away)
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Located in Wallingford, CT / 71 miles away from Pittsfield, MA
2020 Toyota Highlander XLE Certified. CARFAX One-Owner. 20/27 City/Highway MPGLOCAL TRADE, HEATED LEATHER SEATS, PREMIUM SOUND, LOADED WITH LUXURY, 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH3LS517603
Stock: 250965A
Certified Pre-Owned: Yes
Listed since: 08-09-2025 - $11,995good price$1,856 below market
- 118,333 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (66 mi away)
Close
Located in Naugatuck, CT / 66 miles away from Pittsfield, MA
- **Proven Reliability:** Award-winning dependability and quality from J.D. Power and Kelley Blue Book. - **Powerful Performance:** Robust 3.5L V6 en...
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 (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH1CS101004
Stock: 101004N
Certified Pre-Owned: No - $6,450good price$1,877 below market
- 144,525 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 16 City / 22 Hwy MPG
- Choice Motor Car (59 mi away)
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Located in Plainville, CT / 59 miles away from Pittsfield, MA
Nice, clean, loaded up Highlander in great condition inside and out. Leather seats, power sliding sunroof, 4wd, power windows locks and seat, nice ne...
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/22 Highway)
Listing Information:
VIN: JTEEP21A550080550
Stock: 080550
Certified Pre-Owned: No
Listed since: 09-10-2024 - $23,998good price$1,281 below market
- 92,986 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Ocean Honda Groton (96 mi away)
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Located in Groton, CT / 96 miles away from Pittsfield, MA
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seats, 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH6KS626583
Stock: 6E07044
Certified Pre-Owned: No
Listed since: 07-17-2025 - $10,995good price$1,403 below market
- 113,382 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (66 mi away)
Close
Located in Naugatuck, CT / 66 miles away from Pittsfield, MA
- Reliable and powerful 3.5L V6 engine with 270 horsepower - Spacious interior with second-row rear vents and privacy glass - Award-winning family 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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH8BS062068
Stock: 62068N
Certified Pre-Owned: No - $33,211fair price$671 below market
- 62,986 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Lia Toyota of Wilbraham (45 mi away)
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Located in Wilbraham, MA / 45 miles away from Pittsfield, MA
Blueprint 2022 Toyota Highlander XLE 3.5L V6 DOHC 8-Speed Automatic AWDClean Car-Fax *, Service Records Available *, Back Up Camera *, Bluetooth Smart...
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 (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH3NS596205
Stock: NS596205T
Certified Pre-Owned: No
Listed since: 07-15-2025 - Price Drop$28,858great price$2,259 below market
- 35,205 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- McGee Toyota of Putnam (79 mi away)
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Located in Putnam, CT / 79 miles away from Pittsfield, MA
McGee Toyota of Putnam is proud to present you with this 2021 Toyota Highlander LE! ---------- TWO (2) OWNER TRADE-IN, AWD, 3.5L V6 ENGINE, 8-SPE...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBHXMS124723
Stock: 25534B
Certified Pre-Owned: No
Listed since: 06-21-2025 - $18,990good price$1,470 below market
- 126,409 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Toyota of Colchester (76 mi away)
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Located in Colchester, CT / 76 miles away from Pittsfield, MA
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: 5TDJZRFH9JS863793
Stock: 20256A
Certified Pre-Owned: No
Listed since: 07-19-2025
Showing 1 - 21 out of 1,527 listings
Buying a Toyota Highlander in Pittsfield Massachusetts
For those navigating the scenic routes and diverse landscapes around Pittsfield, MA, the Toyota Highlander presents a fitting option with its comfortable and quiet ride. This three-row SUV boasts a smooth performance that can easily handle both urban commuting and weekend adventures in the nearby Berkshire Mountains. With its good power and fuel efficiency from the V6 engine, the Highlander allows drivers to explore local attractions like Tanglewood or the Norman Rockwell Museum without constantly worrying about fuel stops.
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