Used Toyota Grand Highlander for Sale in Cheshire, CT
Buy a luxurious Toyota Grand Highlander in the county seat of New Haven County Connecticut
Skip to Filters
83 listings
- $43,982fair price$60 above market
- 56,085 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 27 Hwy MPG
- Westbrook Toyota (28 mi away)
Close
Located in Westbrook, CT / 28 miles away from Cheshire, CT
XLE trim. Toyota Certified, Superb Condition, CARFAX 1-Owner. FUEL EFFICIENT 27 MPG Hwy/21 MPG City! NAV, 3rd Row Seat, Heated Seats, Back-Up Camera, ...
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 - New Listing$43,998fair price$768 below market
- 29,165 miles
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to CT*
Close
Located in Richmond, VA / 365 miles away from Cheshire, CT
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 - $39,805good price$1,203 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 / 2,194 miles away from Cheshire, CT
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$51,998fair price$889 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 CT*
Close
Located in Modesto, CA / 2,541 miles away from Cheshire, CT
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 - $46,998fair price$1,145 above market
- 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 CT*
Close
Located in Louisville, KY / 709 miles away from Cheshire, CT
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$191 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*
Close
Located in Atlanta, GA / 825 miles away from Cheshire, CT
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$1,399 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 CT*
Close
Located in Sanford, FL / 998 miles away from Cheshire, CT
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 - New Listing$46,998fair price$901 above market
- 18,842 miles
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from MD to CT*
Close
Located in Salisbury, MD / 258 miles away from Cheshire, CT
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: 5TDAAAB59RS042967
Stock: 27103006
Certified Pre-Owned: No - New Listing$46,998fair price$711 above market
- 22,105 miles
- 8 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to CT*
Close
Located in Roseville, CA / 2,528 miles away from Cheshire, CT
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: 5TDAAAB58RS023262
Stock: 27421106
Certified Pre-Owned: No - New Listing
- 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 CT*
Close
Located in Columbus, OH / 541 miles away from Cheshire, CT
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 / 365 miles away from Cheshire, CT
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 / 1,439 miles away from Cheshire, CT
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 CT*
Close
Located in Fredericksburg, VA / 332 miles away from Cheshire, CT
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- Price Drop
- 6,707 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to CT*
Close
Located in Spokane Valley, WA / 2,195 miles away from Cheshire, CT
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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA55RS002399
Stock: 27470417
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 CT*
Close
Located in San Diego, CA / 2,481 miles away from Cheshire, CT
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 CT*
Close
Located in Puyallup, WA / 2,430 miles away from Cheshire, CT
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 - $51,988fair price$36 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*
Close
Located in Cincinnati, OH / 627 miles away from Cheshire, CT
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 - 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 CT*
Close
Located in Puyallup, WA / 2,430 miles away from Cheshire, CT
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- $47,991fair price$1,022 above market
- 32,910 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Smithtown Toyota (47 mi away)
Close
Located in Smithtown, NY / 47 miles away from Cheshire, CT
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: 5TDAAAB57RS056978
Stock: U46906E
Certified Pre-Owned: Yes
Listed since: 07-17-2025 - Price Drop$47,990fair price$926 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 / 1,080 miles away from Cheshire, CT
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 - Price Drop$48,998fair price$1,155 above market
- 11,116 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to CT*
Close
Located in Orlando, FL / 1,017 miles away from Cheshire, CT
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: 5TDAAAB51RS044650
Stock: 27607787
Certified Pre-Owned: No
Showing 43 - 63 out of 83 listings
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.