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2,307 listings
- $35,999fair price$18 below market
- 56,950 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Columbia, SC / 331 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: 5TDLZRAH0NS142350
Stock: 8DL40W
Certified Pre-Owned: No
Listed since: 05-06-2025 - Price Drop$34,000fair price$294 above market
- 36,676 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Hall Toyota Virginia Beach (13 mi away)
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Located in Virginia Beach, VA / 13 miles away from Chesapeake, VA
Celestial Silver Metallic 2020 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC AWD, Front dual zone A/C.AWD, Front dual zone A/C, 18" Machi...
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: 5TDHZRBH8LS510985
Stock: 24255528A
Certified Pre-Owned: No
Listed since: 05-07-2025 - New Listing$40,998fair price$1,088 above market
- 16,120 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 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDJZRAH1NS119263
Stock: 27478715
Certified Pre-Owned: No - New Listing$34,998fair price$282 below market
- 51,778 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH3LS011140
Stock: 25830433
Certified Pre-Owned: No - New Listing$36,680fair price$620 below market
- 35,577 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Mark Jacobson Toyota (162 mi away)
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Located in Durham, NC / 162 miles away from Chesapeake, VA
Come to Mark Jacobson Toyota and check out this. 2022 Toyota Highlander XLE In our two story indoor showroom! New Price! Certified. Blueprint FWD 8-Sp...
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: 5TDHZRAH9NS131627
Stock: 80171A
Certified Pre-Owned: No
Listed since: 06-08-2025 - $34,244fair price$598 below market
- 49,559 miles
- No accidents, 2 owners, rental vehicle
- 7 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
Priced below KBB Fair Purchase Price! *Full Family Plan* INCLUDES OIL CHANGES FOR LIFE!, Alloy wheels / Premium Wheels, Bluetooth, Hands-Free, Leather...
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: 5TDGZRAH1NS099882
Stock: SX061913A
Certified Pre-Owned: No
Listed since: 04-20-2025 - Price Drop$34,998good price$1,283 below market
- 52,385 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to VA*
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Located in Henderson, NV / 2,143 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: 5TDJZRAH2NS094907
Stock: 27063548
Certified Pre-Owned: No - $37,300fair price$333 below market
- 48,778 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Greensboro Auto Center (199 mi away)
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Located in Greensboro, NC / 199 miles away from Chesapeake, VA
2 YEARS COMPLIMENTARY MAINTENANCE (for vehicles 100,000 miles or less. See Dealer for details.) COMPLIMENTARY TIRE ROTATIONS FOR LIFE (with any servic...
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: 5TDHZRBH8NS580148
Stock: 3204
Certified Pre-Owned: No
Listed since: 03-21-2025 - $33,998fair price$176 below market
- 56,480 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Crown Motor (159 mi away)
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Located in Fuquay Varina, NC / 159 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: 5TDGZRAH6NS106731
Stock: 106731
Certified Pre-Owned: No
Listed since: 05-13-2025 - Price Drop$36,998great price$3,214 below market
- 33,849 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
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Located in Bogart, GA / 452 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH4NS236361
Stock: 27361094
Certified Pre-Owned: No - New Listing$38,000fair price$616 below market
- 36,669 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Hall Toyota Elizabeth City (31 mi away)
- Home delivery*
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Located in Elizabeth City, NC / 31 miles away from Chesapeake, VA
We are currently offering Vehicle Purchase Home Delivery by appointment. Please contact for details.. Blueprint LE FWD 8-Speed Automatic 2.4L I4 PDI T...
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: 5TDKDRAH4RS547255
Stock: 22255037A
Certified Pre-Owned: No
Listed since: 03-19-2025 - $31,499fair price$219 below market
- 50,945 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Pittsburgh, PA / 330 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: 5TDBZRBH0NS256925
Stock: 8D0FXJ
Certified Pre-Owned: No
Listed since: 05-01-2025 - Price Drop$41,590fair price$389 above market
- 49,591 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Oklahoma City, OK / 1,189 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH1NS187180
Stock: 2003725614
Certified Pre-Owned: No
Listed since: 05-15-2025 - New Listing$26,399good price$1,334 below market
- 92,800 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carget Motors (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
The 2020 Toyota Highlander XLE is a refined and versatile midsize SUV that seamlessly blends comfort, technology, and practicality. With its sleek, mo...
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: 5TDHZRBH0LS038653
Stock: 038653
Certified Pre-Owned: No
Listed since: 06-06-2025 - New Listing$31,999fair price$15 below market
- 48,889 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Monroeville, PA / 317 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: 5TDBZRBH6NS253348
Stock: 8D6SL0
Certified Pre-Owned: No
Listed since: 05-14-2025 - New Listing$35,590fair price$656 below market
- 54,114 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Indianapolis, IN / 578 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH2NS174401
Stock: 2003722981
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$37,998fair price$88 above market
- 18,674 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 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: 5TDHZRAH2NS132991
Stock: 27307816
Certified Pre-Owned: No - $35,366fair price$13 below market
- 68,855 miles
- No accidents, 1 owner, personal use only
- 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. White 2022 Toyota Highlander XSE AWD 8-Speed Automatic 3.5L V6 DOHC CARFAX One-Owner. CERTIFIED 7 YEAR/ 100,000 MILE WARRANTY.Our best av...
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: 5TDLZRBH2NS254954
Stock: 13100PJ
Certified Pre-Owned: No
Listed since: 05-14-2025 - New Listing$31,635fair price$271 below market
- 49,563 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- Fred Anderson Toyota (152 mi away)
Close
Located in Raleigh, NC / 152 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. *Full Family Plan* INCLUDES OIL CHANGES FOR LIFE!, Still Under Factory Powertrain Warranty!!, Only One Owner and Accid...
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: 5TDZZRAH1NS551306
Stock: NS551306P
Certified Pre-Owned: Yes
Listed since: 05-23-2025 - Price Drop
- 14,671 miles
- 1 accident, 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 Lynnwood, WA / 2,437 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: Yes
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBHXNS201822
Stock: 26747483
Certified Pre-Owned: No - $24,995fair price$1,222 below market
- 83,459 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Nation Motors (91 mi away)
Close
Located in Richmond, VA / 91 miles away from Chesapeake, VA
2020 TOYOTA HIGHLANDER LE FRONT WHEEL DRIVE {Sub Title} with powerful 3.5L V6 DOHC -INC DUAL OVERHEAD CAM AND ALUMINUM engine and driven 83459 miles! ...
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: 5TDZZRAH7LS500597
Stock: NM3173
Certified Pre-Owned: No
Showing 358 - 378 out of 2,307 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Rolling again
Ken S, 10/28/2021
2022 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
Just replaced a 2018 Highlander due to accident. Of course the car is comfortable and nice to drive but I especially appreciate it after the accident. The 2018 was totaled because of a head on collision. My wife and I only had minor injuries that I attribute to the strength of the vehicle and the air bags that completely isolated us.
Used 2022 Toyota Highlander in Chesapeake, VA Values
Estimated values
2022 Toyota Highlander XSE 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $30,632 | $32,362 | $34,167 |
| Clean | $30,118 | $31,793 | $33,540 |
| Average | $29,260 | $30,846 | $32,497 |
| Rough | $28,146 | $29,615 | $31,140 |
The average list price of a used 2022 Toyota Highlander in Chesapeake, Virginia is $35,394. The average mileage on a used Toyota Highlander 2022 for sale in Chesapeake, Virginia is 47,923. Based on the average mileage of 47,923 for used 2022 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 2022 in Chesapeake, Virginia to be $29,260.
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