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2,162 listings
- Price Drop$31,200good price$1,324 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 - New Listing$30,590fair price$419 below market
- 90,214 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Chicago, IL / 745 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: 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: 5TDHZRBH0MS545456
Stock: 2003665052
Certified Pre-Owned: No
Listed since: 04-29-2025 - $40,998fair price$827 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: Yes
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH7PS527061
Stock: 26947971
Certified Pre-Owned: No - $24,180good price$1,347 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$141 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 - Price Drop$30,597fair price$233 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)
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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: 5TDKDRAHXPS501605
Stock: RPS501605
Certified Pre-Owned: No
Listed since: 04-30-2025 - $37,999good price$1,750 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*
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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 - Price Drop$30,597fair price$234 below market
- 49,470 miles
- No accidents, 1 owner, rental vehicle
- 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: 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 - Price Drop$29,999good price$1,114 below market
- 38,560 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Union, NJ / 293 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Satellite Radio,WiF...
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: 5TDBZRBH4MS526494
Stock: MS526494T
Certified Pre-Owned: No - Price Drop$29,900good price$1,098 below market
- 46,180 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Southern Ford (33 mi away)
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Located in Newport News, VA / 33 miles away from Chesapeake, VA
Clean CARFAX. Odometer is 34011 miles below market average!Certified. Alumina Jade Metallic 2019 Toyota Highlander XLE 8-Speed Automatic 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH1KS724100
Stock: XP10648A
Certified Pre-Owned: No
Listed since: 05-14-2025 - Price Drop$21,989good price$758 below market
- 138,538 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Leith Toyota (143 mi away)
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Located in Raleigh, NC / 143 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: 5TDJZRFH1KS568026
Stock: T568026A
Certified Pre-Owned: No
Listed since: 05-15-2025 - Price Drop$31,992good price$1,709 below market
- 34,181 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Reynolds Subaru (147 mi away)
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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$1,057 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 - $30,398fair price$932 below market
- 61,777 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Lauderdale Lakes, FL / 768 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/29 Highway)
Listing Information:
VIN: 5TDGZRAH5MS051137
Stock: 7VGLJY
Certified Pre-Owned: No
Listed since: 03-06-2025 - Price Drop$34,605good price$2,137 below market
- 68,062 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Lexington, KY / 455 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wheel,Keyless Sta...
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: 5TDFZRBH6MS093293
Stock: MS093293P
Certified Pre-Owned: No - New Listing$36,998good price$1,557 below market
- 45,753 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from LA to VA*
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Located in Baton Rouge, LA / 959 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: Yes
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDFZRAH3MS047891
Stock: 27159777
Certified Pre-Owned: No - $25,000good price$881 below market
- 60,330 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 19 City / 26 Hwy MPG
- Koons Ford Baltimore (180 mi away)
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Located in Baltimore, MD / 180 miles away from Chesapeake, VA
The 2019 Toyota Highlander LE blends practicality, comfort, and trusted reliability in a versatile midsize SUV. Powered by a 3.5L V6 engine paired wit...
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 (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH2KS997731
Stock: KS997731
Certified Pre-Owned: No
Listed since: 05-26-2025 - New Listing$25,590fair price
- 86,860 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in San Antonio, TX / 1,380 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/29 Highway)
Listing Information:
VIN: 5TDCZRAH2MS082523
Stock: 2003707077
Certified Pre-Owned: No
Listed since: 05-16-2025 - New Listing$24,500fair price$605 below market
- 103,294 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Heritage Toyota Owings Mills (187 mi away)
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Located in Owings Mills, MD / 187 miles away from Chesapeake, VA
Recent Arrival! AWD. Clean CARFAX. AWD 8-Speed Automatic Electronic with ECT-i 3.5L V6*Your additional costs are tax, tag, title, registration, and e...
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: 5TDJZRFH8KS582120
Stock: 7J582120
Certified Pre-Owned: No
Listed since: 06-03-2025 - $32,999good price$2,134 below market
- 36,307 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Wexford, PA / 339 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remo...
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: 5TDGZRBH3MS541154
Stock: H541154
Certified Pre-Owned: No - $42,998fair price$776 above market
- 13,824 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax Virginia Beach (10 mi away)
Close
Located in Virginia Beach, VA / 10 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: 5TDKDRBH2PS045811
Stock: 27431966
Certified Pre-Owned: No
Showing 211 - 231 out of 2,162 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 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander LE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $24,737 | $26,923 | $29,115 |
| Clean | $24,211 | $26,337 | $28,466 |
| Average | $23,333 | $25,359 | $27,384 |
| Rough | $22,192 | $24,088 | $25,977 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $31,625. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 57,140. Based on the average mileage of 57,140 for used 2021 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 2021 in Chesapeake, Virginia to be $23,333.
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