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2,135 listings
- Price Drop$40,594good price$1,764 below market
- 18,410 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Lynchburg Nissan (172 mi away)
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Located in Forest, VA / 172 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. AWD. Maroon 2023 Toyota Highlander XLE 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: 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: 5TDKDRBH4PS040657
Stock: P18670
Certified Pre-Owned: No
Listed since: 01-30-2025 - $36,550good price$1,820 below market
- 34,966 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
Close
Located in Chesapeake, VA / 2 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH6PS047725
Stock: PS047725P
Certified Pre-Owned: No - Price Drop$32,997good price$1,833 below market
- 34,123 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
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Located in Cary, NC / 155 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 - $32,999fair price$1,236 below market
- 34,510 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS520222
Stock: 8FVSFG
Certified Pre-Owned: No
Listed since: 04-10-2025 - $31,499good price$1,922 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 - $40,998fair price$805 below market
- 17,671 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax Harrisonburg (187 mi away)
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Located in Harrisonburg, VA / 187 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 - $43,998fair price$52 below market
- 14,018 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax Potomac Mills (145 mi away)
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Located in Woodbridge, VA / 145 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: 5TDKDRBH4PS013748
Stock: 27286537
Certified Pre-Owned: No - $37,999good price$1,830 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 - Price Drop$33,895fair price$437 above market
- 39,094 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Trust Auto (193 mi away)
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Located in Sykesville, MD / 193 miles away from Chesapeake, VA
You can find this Loaded 2021 Toyota Highlander XLE 7-Passenger SUV FWD (Front Wheel Drive) and many others like it at Trust Auto. This Toyota include...
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: 5TDGZRAHXMS044670
Stock: 044670
Certified Pre-Owned: No
Listed since: 04-22-2025 - $37,900fair price$481 above market
- 46,360 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Hanna Imports (148 mi away)
Close
Located in Raleigh, NC / 148 miles away from Chesapeake, VA
*Carfax Accident Free*, *Multi Point Inspection*, 3rd row seats: split-bench, Alloy wheels, Auto High-beam Headlights, Automatic temperature control, ...
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: 5TDKDRAH7PS020159
Stock: 3021538
Certified Pre-Owned: No
Listed since: 04-23-2025 - Price Drop$36,987good price$1,836 below market
- 36,776 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Heritage Volkswagen Catonsville (179 mi away)
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Located in Baltimore, MD / 179 miles away from Chesapeake, VA
Recent Arrival! *ALL WHEEL DRIVE*, *POWER DRIVERS SEAT*, *HEATED LEATHER SEATS*, *POWER SUNROOF*, *BACKUP CAMERA*, *HANDS FREE BLUETOOTH*, *APPLE CARP...
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: 5TDKDRBH5PS017372
Stock: 8VU17372
Certified Pre-Owned: No
Listed since: 03-11-2025 - $38,598fair price$994 above market
- 57,162 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Crossroads INFINITI of Raleigh (143 mi away)
Close
Located in Raleigh, NC / 143 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. 2021 Toyota HighlanderClean Carfax, One Owner, 20" Painted Alloy Wheels, Apple CarPlay/Android Auto, Auto High-beam He...
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: 5TDFZRAH2MS064374
Stock: PU4374
Certified Pre-Owned: No
Listed since: 04-22-2025 - New Listing$31,999fair price$574 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 - $30,055good price$1,483 below market
- 99,625 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Koons of Woodbridge (142 mi away)
Close
Located in Woodbridge, VA / 142 miles away from Chesapeake, VA
Visit Koons Automotive of Woodbridge online at www.koonsofwoodbridge.com to see more pictures of this vehicle or call us at 571-285-3277 today to sch...
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: 5TDJZRBH3MS097084
Stock: 36516
Certified Pre-Owned: No - $37,000good price$1,032 below market
- 38,479 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
Close
Located in Richmond, VA / 90 miles away from Chesapeake, VA
*Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*
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: 5TDKDRAH8PS048472
Stock: J6883
Certified Pre-Owned: No
Listed since: 05-22-2025 - $35,900good price$1,430 below market
- 25,677 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Hanna Imports (148 mi away)
Close
Located in Raleigh, NC / 148 miles away from Chesapeake, VA
Leather Seats, Bluetooth, *Multi Point Inspection*, Highlander XLE, AWD, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, Power Liftgate, Pow...
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: 5TDGZRBH1MS094422
Stock: 3021587
Certified Pre-Owned: No
Listed since: 04-27-2025 - $30,000fair price$343 below market
- 75,970 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Tysons Toyota (162 mi away)
- Five Star Dealer
Close
Located in Vienna, VA / 162 miles away from Chesapeake, VA
AWD.RECALL NOTICE: Some vehicles offered for sale may be subject to unrepaired manufacturer safety recalls. To determine the recall status of a vehi...
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: 5TDHZRBH2MS531137
Stock: 0252688A
Certified Pre-Owned: No
Listed since: 05-23-2025 - Price Drop$31,000fair price$782 below market
- 55,314 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
Close
Located in Richmond, VA / 90 miles away from Chesapeake, VA
*Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*
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: 5TDKDRAH3PS008994
Stock: J6710
Certified Pre-Owned: No
Listed since: 04-04-2025 - Price Drop$42,500fair price$275 below market
- 28,188 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Ourisman Kia of Fairfax (158 mi away)
Close
Located in Fairfax, VA / 158 miles away from Chesapeake, VA
Clean CARFAX. Odometer is 1561 miles below market average!2023 Toyota Highlander XSE AWD Blueprint*3rd Row Seating*, Blind Spot Monitor, Backup Came...
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: 5TDKDRBH3PS000179
Stock: M2456
Certified Pre-Owned: No
Listed since: 05-07-2025 - $32,984good price$888 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 - Price Drop$29,460fair price$417 below market
- 56,922 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Johnson Lexus of Raleigh (144 mi away)
Close
Located in Raleigh, NC / 144 miles away from Chesapeake, VA
JUST ARRIVED!! DETAILS COMING SOON!This vehicle is located at Johnson Lexus of Raleigh.Here at Johnson Lexus we price our cars online aggressively ...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH0MS068131
Stock: D42298B
Certified Pre-Owned: No
Listed since: 04-26-2025
Showing 106 - 126 out of 2,135 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 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander XLE 4dr SUV AWD (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $31,720 | $33,560 | $35,635 |
| Clean | $31,322 | $33,105 | $35,113 |
| Average | $30,660 | $32,345 | $34,245 |
| Rough | $29,799 | $31,358 | $33,115 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $35,520. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 42,099. Based on the average mileage of 42,099 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 $30,660.
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