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2,090 listings
- Price Drop$31,300good price$2,246 below market
- 42,997 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Koons Arlington Toyota (157 mi away)
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Located in Arlington, VA / 157 miles away from Chesapeake, VA
2023 Toyota Highlander LE CarFax 1 Owner, Bluetooth, Automatic temperature control, Power Liftgate. Arlington Toyota is a One Price Dealership. No Hag...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS027784
Stock: R10812
Certified Pre-Owned: No
Listed since: 05-20-2025 - New Listing$40,998good price$1,584 below market
- 18,840 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax Raleigh (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4PS521915
Stock: 27446565
Certified Pre-Owned: No - $24,051fair price$462 below market
- 99,412 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Len Stoler Chevrolet (199 mi away)
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Located in Westminster, MD / 199 miles away from Chesapeake, VA
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: 5TDJZRFH8KS614113
Stock: BV1345
Certified Pre-Owned: No
Listed since: 04-21-2025 - New Listing$39,590fair price$412 below market
- 15,693 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana - Richmond (99 mi away)
- Home delivery*
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Located in Richmond, VA / 99 miles away from Chesapeake, VA
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: 5TDKDRBH8PS005345
Stock: 2003648907
Certified Pre-Owned: No
Listed since: 05-06-2025 - Price Drop$31,200good price$1,526 below market
- 23,727 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Lexus of Silver Spring (165 mi away)
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Located in Silver Spring, MD / 165 miles away from Chesapeake, VA
2021 Toyota Highlander LE CARFAX One-Owner.Magnetic Gray Metallic AWD, 18 Painted Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel ...
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: 5TDBZRBH8MS532749
Stock: P1D1500
Certified Pre-Owned: No
Listed since: 03-21-2025 - Price Drop$32,997good price$1,762 below market
- 34,123 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (156 mi away)
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Located in Cary, NC / 156 miles away from Chesapeake, VA
At EchoPark, it’s all about offering you options for a happy experience. We have thousands of new-to-you makes and models that range from sedans to tr...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH0PS046344
Stock: CPS046344A
Certified Pre-Owned: No
Listed since: 05-05-2025 - $37,499fair price$1,004 below market
- 1,356 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- JT Auto Group (191 mi away)
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Located in Sanford, NC / 191 miles away from Chesapeake, VA
2021 Toyota Highlander XLE *3RD SEAT, *BLUE TOOTH READY, *HEATED SEATS, *KEYLESS ENTRY, *LEATHER SEATS, *NAVIGATION, *NEW TIRES, *SATELITE RADIO, *USB...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAH8MS063119
Stock: J3416
Certified Pre-Owned: No - Price Drop$35,996good price$1,218 below market
- 19,291 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- BMW of Southpoint (162 mi away)
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Located in Durham, NC / 162 miles away from Chesapeake, VA
EXCELLENT SAFETY FOR YOUR FAMILYBlind Spot Monitor, Cross-Traffic Alert, Lane Keeping Assist, Child Safety Locks, Dynamic Stability Control (including...
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: 5TDGZRBH9MS159663
Stock: XB0269
Certified Pre-Owned: No
Listed since: 02-06-2025 - $35,999good price$1,087 below market
- 53,853 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales Fayetteville (193 mi away)
- Home delivery*
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Located in Fayetteville, NC / 193 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS003695
Stock: 7VDN1H
Certified Pre-Owned: No
Listed since: 04-16-2025 - $40,998fair price$1,037 below market
- 17,671 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax Harrisonburg (186 mi away)
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Located in Harrisonburg, VA / 186 miles away from Chesapeake, VA
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: 5TDKDRBH7PS527061
Stock: 26947971
Certified Pre-Owned: No - $35,998fair price$391 below market
- 29,484 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
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Located in Spokane Valley, WA / 2,203 miles away from Chesapeake, VA
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 (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH1MS552525
Stock: 27099778
Certified Pre-Owned: No - $37,999good price$1,951 below market
- 41,584 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales Newport News (28 mi away)
- Home delivery*
Close
Located in Newport News, VA / 28 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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: 5TDKDRBH1PS045864
Stock: 8F5Y80
Certified Pre-Owned: No
Listed since: 02-25-2025 - New Listing$39,321fair price$566 below market
- 17,630 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Fairfax Toyota (158 mi away)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
Certified. 0218 2021 Toyota Highlander Limited AWD 8-Speed Automatic 3.5L V6 DOHC CARFAX One-Owner. Clean CARFAX. CERTIFIED 7 YEAR/ 100,000 MILE WARRA...
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: 5TDDZRBH4MS161047
Stock: 231553A
Certified Pre-Owned: No
Listed since: 05-04-2025 - Price Drop$30,597fair price$441 below market
- 48,203 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (156 mi away)
Close
Located in Cary, NC / 156 miles away from Chesapeake, VA
At EchoPark, it’s all about offering you options for a happy experience. We have thousands of new-to-you makes and models that range from sedans to tr...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS501605
Stock: RPS501605
Certified Pre-Owned: No
Listed since: 04-30-2025 - New Listing$26,990good price
- 105,765 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Dallas, TX / 1,195 miles away from Chesapeake, VA
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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH9MS118742
Stock: 2003661721
Certified Pre-Owned: No
Listed since: 04-23-2025 - Price Drop$30,597fair price$451 below market
- 49,470 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (156 mi away)
Close
Located in Cary, NC / 156 miles away from Chesapeake, VA
At EchoPark, it’s all about offering you options for a happy experience. We have thousands of new-to-you makes and models that range from sedans to tr...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS500908
Stock: RPS500908
Certified Pre-Owned: No
Listed since: 04-30-2025 - $24,180good price$1,333 below market
- 95,827 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Waldorf Chevrolet (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
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: 5TDJZRFH7KS613826
Stock: FFF0678A
Certified Pre-Owned: No
Listed since: 05-16-2025 - $36,000fair price$159 below market
- 33,639 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- DARCARS Toyota of Silver Spring (165 mi away)
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Located in Silver Spring, MD / 165 miles away from Chesapeake, VA
2023 Toyota Highlander XLE CARFAX One-Owner.Magnetic Gray FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic Odometer is 875...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS004683
Stock: 52A2107A
Certified Pre-Owned: No
Listed since: 04-22-2025 - $29,987good price$1,639 below market
- 59,343 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in New Port Richey, FL / 699 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keepi...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAH3MS533332
Stock: MS533332P
Certified Pre-Owned: No - Price Drop$31,992good price$1,821 below market
- 34,181 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Reynolds Subaru (147 mi away)
Close
Located in Orange, VA / 147 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Ruby Flare Pearl 2023 Toyota Highlander LE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp ...
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: 5TDKDRBH2PS036168
Stock: 38891P
Certified Pre-Owned: No
Listed since: 05-03-2025 - $34,999fair price$935 below market
- 65,942 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Oklahoma City, OK / 1,187 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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 (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH7MS092001
Stock: 8DT32R
Certified Pre-Owned: No
Listed since: 04-16-2025
Showing 190 - 210 out of 2,090 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Couldn’t be happier!
S Curry, 01/02/2021
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
I’ve been eyeing the Highlander since they redesigned it in 2020. I opted for the Limited AWD trim with the optional 12 inch screen and bench seats. I am completely blown away on how amazing it is to drive the Highlander. Visibility is great but with the bigger screen you also get birds eye view which will definitely help assess your surroundings. The safety features are awesome and the … little things like intuitive climate control are nice. I was worried about access into the third row and comfort but my 12 year old is happy with it. The middle row does slide up giving more leg room to the third row. I came from a minivan so I am used to a lot of cargo room and low entry. If you will be using the third row consistently I recommend getting the cross bars and on roof cargo storage to maximize what you can carry, and if you are transporting smaller kids/adults the step up may be just slightly too high for them but running boards can be installed.
Used 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $26,770 | $28,763 | $31,012 |
| Clean | $26,435 | $28,372 | $30,558 |
| Average | $25,876 | $27,721 | $29,802 |
| Rough | $25,149 | $26,875 | $28,820 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $33,776. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 43,240. Based on the average mileage of 43,240 for used 2023 Toyota Highlander for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Toyota Highlander 2023 in Chesapeake, Virginia to be $25,876.
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