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2,129 listings
- Price Drop$28,716fair price$17 below market
- 75,956 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Spokane, WA / 2,208 miles away from Chesapeake, VA
CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote ...
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: 5TDBZRBH4MS526298
Stock: MS526298B
Certified Pre-Owned: No - New Listing$39,998fair price$240 above market
- 16,876 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax Potomac Mills (144 mi away)
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Located in Woodbridge, VA / 144 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: 5TDKDRAH4PS025903
Stock: 27273965
Certified Pre-Owned: No - New Listing$37,998fair price$501 below market
- 57,061 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
Close
Located in Puyallup, WA / 2,435 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: 5TDFZRBH3MS152199
Stock: 27469577
Certified Pre-Owned: No - New Listing$37,998fair price$755 below market
- 56,195 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
Close
Located in Kennesaw, GA / 507 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: 5TDFZRBH8MS075068
Stock: 27355835
Certified Pre-Owned: No - New Listing$31,998good price$1,556 below market
- 59,336 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Orlando, FL / 643 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/29 Highway)
Listing Information:
VIN: 5TDLZRAH9MS067193
Stock: 27462728
Certified Pre-Owned: No - New Listing$35,998fair price
- 44,464 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in San Antonio, TX / 1,381 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/29 Highway)
Listing Information:
VIN: 5TDYZRAH4MS520240
Stock: 27295397
Certified Pre-Owned: No - $37,681fair price$257 below market
- 51,540 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Toyota of Goldsboro (134 mi away)
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Located in Goldsboro, NC / 134 miles away from Chesapeake, VA
CARFAX One-Owner. Moon Dust 2023 Toyota Highlander XLE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp Toyota Certified, An...
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: 5TDKDRAH4PS020202
Stock: P3759
Certified Pre-Owned: Yes
Listed since: 05-13-2025 - $30,290good price$1,710 below market
- 61,791 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Antwerpen Toyota (175 mi away)
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Located in Clarksville, MD / 175 miles away from Chesapeake, VA
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: 5TDGZRBH0MS130519
Stock: 1671PR
Certified Pre-Owned: No
Listed since: 03-07-2025 - Price Drop$26,988good price$1,210 below market
- 76,354 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Sheehy Toyota of Fredericksburg (126 mi away)
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Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
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: 5TDZZRAH2MS535811
Stock: FR9332P
Certified Pre-Owned: Yes
Listed since: 05-22-2025 - $31,199fair price$635 below market
- 57,301 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Reseda, CA / 2,368 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH0MS521378
Stock: 8CQJFR
Certified Pre-Owned: No
Listed since: 02-14-2025 - Price Drop$36,590fair price$238 below market
- 72,538 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (150 mi away)
- Home delivery*
Close
Located in Springfield, VA / 150 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH0PS507105
Stock: SS188143A
Certified Pre-Owned: No - Price Drop
- 59,251 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from MO to VA*
Close
Located in Independence, MO / 1,000 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH9MS137361
Stock: 27015180
Certified Pre-Owned: No - New Listing$24,967good price$1,319 below market
- 91,662 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Fred Anderson Toyota (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
Clean CARFAX. *Full Family Plan* INCLUDES OIL CHANGES FOR LIFE!, Accident Free Carfax!!, Alloy wheels / Premium Wheels, Bluetooth, Hands-Free, 3rd Row...
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: 5TDZZRAH3MS528690
Stock: ST073319A
Certified Pre-Owned: No
Listed since: 06-07-2025 - New Listing$24,000fair price$637 below market
- 61,897 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 24 Hwy MPG
- Koons Arlington Toyota (157 mi away)
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Located in Arlington, VA / 157 miles away from Chesapeake, VA
2019 Toyota Highlander LE 3rd row seats: split-bench, Air Conditioning, Auto High-beam Headlights, Electronic Stability Control, Four wheel independen...
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/24 Highway)
Listing Information:
VIN: 5TDZARFH2KS049531
Stock: 10844
Certified Pre-Owned: No
Listed since: 06-07-2025 - New Listing$36,000good price$1,601 below market
- 45,122 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Koons Woodbridge Ford (145 mi away)
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Located in Woodbridge, VA / 145 miles away from Chesapeake, VA
Recent Arrival! Priced below KBB Fair Purchase Price! 2023 Toyota Highlander XLE Ruby Flare PearlAWD, 6 Speakers, Alloy wheels, AM/FM radio: SiriusX...
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: 5TDKDRBHXPS046866
Stock: KWFP230178
Certified Pre-Owned: No
Listed since: 06-05-2025 - $34,998fair price
- 52,566 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in San Antonio, TX / 1,370 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: 5TDJZRAH5MS050415
Stock: 27057480
Certified Pre-Owned: No - $31,999fair price$33 above market
- 52,052 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales Fayetteville (193 mi away)
- Home delivery*
Close
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: 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: 5TDKDRAH8PS018582
Stock: 8D0JG5
Certified Pre-Owned: No
Listed since: 04-16-2025 - $36,998fair price$36 above market
- 19,421 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Daytona Beach, FL / 593 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: 5TDGZRAH9MS052503
Stock: 27300328
Certified Pre-Owned: No - Price Drop$34,999fair price$145 above market
- 62,103 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Ramsey, NJ / 319 miles away from Chesapeake, VA
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: 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: 5TDLZRBH6MS079090
Stock: B8279P
Certified Pre-Owned: No - New Listing$36,998fair price$205 below market
- 67,501 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Buena Park, CA / 2,345 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: 5TDFZRBH8MS071912
Stock: 27478772
Certified Pre-Owned: No - New Listing$36,998fair price
- 53,792 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in McKinney, TX / 1,179 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: 5TDDZRBHXMS533698
Stock: 26867803
Certified Pre-Owned: No
Showing 274 - 294 out of 2,129 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 | $25,097 | $27,186 | $29,281 |
| Clean | $24,563 | $26,593 | $28,629 |
| Average | $23,672 | $25,606 | $27,541 |
| Rough | $22,515 | $24,322 | $26,126 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $33,686. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 56,894. Based on the average mileage of 56,894 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 $23,672.
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