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2,160 listings
- $30,290good price$1,704 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$1,200 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$587 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*
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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 - New Listing$33,998fair price$222 below market
- 65,620 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Colma, CA / 2,518 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: 5TDYZRAH4MS088782
Stock: 27006309
Certified Pre-Owned: No - Price Drop$36,590fair price$187 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*
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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*
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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$43,998fair price$576 below market
- 16,708 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax Capital Boulevard (142 mi away)
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Located in Raleigh, NC / 142 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: 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: 5TDKDRBH5PS016822
Stock: 27249604
Certified Pre-Owned: No - New Listing$24,000fair price$664 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: 06-08-2025 - New Listing$24,967good price$1,288 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$36,000good price$1,595 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: 06-06-2025 - $31,999fair price$100 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*
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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: 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$115 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*
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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$139 above market
- 62,103 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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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$24,996fair price$645 below market
- 92,312 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 27 Hwy MPG
- Parkway of Wilmington Used Cars (195 mi away)
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Located in Wilmington, NC / 195 miles away from Chesapeake, VA
How about this great vehicle! It just arrived on our lot, and surely won't be here long! Toyota prioritized practicality, efficiency, and style by inc...
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: 5TDKZRFH1KS347479
Stock: 25H0410A
Certified Pre-Owned: No
Listed since: 06-06-2025 - 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*
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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 - $35,499fair price$79 above market
- 56,818 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Tempe, AZ / 2,023 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: 5TDDZRBHXMS158296
Stock: 8D1CCF
Certified Pre-Owned: No
Listed since: 05-05-2025 - $36,998fair price$204 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*
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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 - Price Drop$35,333fair price$546 below market
- 75,188 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Pocatello, ID / 1,952 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wheel,K...
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: 5TDFZRBH2MS065216
Stock: MS065216A
Certified Pre-Owned: No - Price Drop$29,998fair price$703 above market
- 22,652 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 19 City / 26 Hwy MPG
- CarMax Fayetteville (191 mi away)
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Located in Fayetteville, NC / 191 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: 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:
22 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH5KS717526
Stock: 27095250
Certified Pre-Owned: No - Price Drop$22,888great price$2,274 below market
- 128,387 miles
- 1 accident, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in North Brunswick, NJ / 273 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
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: 5TDGZRAH1MS070221
Stock: SS044301A
Certified Pre-Owned: No - Price Drop$22,920fair price$159 above market
- 88,462 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CMA's Colonial Chevrolet (78 mi away)
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Located in Chester, VA / 78 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDZZRFH6KS334225
Stock: C6610C
Certified Pre-Owned: No
Listed since: 05-29-2025
Showing 295 - 315 out of 2,160 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 XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,084 | $29,100 | $31,122 |
| Clean | $26,507 | $28,466 | $30,428 |
| Average | $25,546 | $27,409 | $29,271 |
| Rough | $24,297 | $26,035 | $27,768 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $31,984. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 63,187. Based on the average mileage of 63,187 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 $25,546.
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