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2,135 listings
- Price Drop$29,990great price$2,621 below market
- 55,279 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
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Located in Richmond, VA / 100 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS032037
Stock: 2003617452
Certified Pre-Owned: No
Listed since: 04-15-2025 - $28,966great price$3,409 below market
- 33,836 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Global Auto Outlet (150 mi away)
Close
Located in Temple Hills, MD / 150 miles away from Chesapeake, VA
Estimated monthly payment and estimated total purchase price include the Maryland processing fee of $800 (not required by law). Taxes and additional f...
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: 5TDKDRAH0PS504724
Stock: 504724
Certified Pre-Owned: No
Listed since: 11-16-2024 - New Listing
- 28,801 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota 40 (187 mi away)
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Located in Edgewood, MD / 187 miles away from Chesapeake, VA
**1-Owner**Leather**Sunroof**Apple Car Play**AWD**CARFAX One-Owner. Clean CARFAX. 20/27 City/Highway MPG This 2022 Dark Blue Toyota Highlander XSE A...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDLZRBH3NS207755
Stock: P2733
Certified Pre-Owned: No
Listed since: 05-30-2025 - Price Drop$25,900great price$3,266 below market
- 72,924 miles
- No accidents, 3 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- DARCARS Toyota of Baltimore (177 mi away)
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Located in Baltimore, MD / 177 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Recent Arrival! Clean CARFAX.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, FWD, Magnetic Gray, Graph...
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: 5TDGZRAH1MS067951
Stock: 52E2032A
Certified Pre-Owned: No
Listed since: 04-30-2025 - Price Drop$29,397great price$3,231 below market
- 37,671 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
Close
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: 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: 5TDKDRAH9PS041322
Stock: RPS041322
Certified Pre-Owned: No
Listed since: 04-01-2025 - $34,395great price$3,358 below market
- 46,150 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Capital Ford (144 mi away)
Close
Located in Raleigh, NC / 144 miles away from Chesapeake, VA
Leather, Sunroof, Heated Seats, Apple Carplay/Android Auto, Active Cruise Control, Heated Front Bucket Seats, Power Liftgate.Your Powerhouse Dealer!Ca...
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: 5TDKDRAH8PS013639
Stock: PB60929
Certified Pre-Owned: No
Listed since: 01-20-2025 - New Listing
- 96,504 miles
- 7 Seats, 20 City / 27 Hwy MPG
- John Hiester Chrysler Jeep Dodge Ram (170 mi away)
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Located in Lillington, NC / 170 miles away from Chesapeake, VA
ONE OWNER ACCIDENT FREE CARFAX, AWD, FAST AND EASY FINANCING, THE NEW PRICE OUTLET, AWD, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Br...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH8NS180221
Stock: P10077
Certified Pre-Owned: No
Listed since: 05-28-2025 - Price Drop$30,700great price$2,602 below market
- 44,779 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 3rd row seats: split-bench, ABS brakes, Active Cruise Control, Alloy wheels, Brake assist, Electronic Stability Control, Fro...
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: 5TDKDRAH1PS505218
Stock: R10799
Certified Pre-Owned: No
Listed since: 05-09-2025 - $30,495great price$2,516 below market
- 76,757 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **Local Trade!** **V6!** **AWD!** **Priced to Sell!** **Premium Audio!** **Black Emblems!** **Family Fun!** **Ask For a Video Walk...
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: 5TDHZRBH7MS148584
Stock: 0N38039A
Certified Pre-Owned: Yes
Listed since: 05-02-2025 - New Listing$27,998great price$3,393 below market
- 99,428 miles
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Frederick (173 mi away)
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Located in Gaithersburg, MD / 173 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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBHXMS141904
Stock: 27449558
Certified Pre-Owned: No - $27,000great price$2,167 below market
- 87,698 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Honda of Laurel (166 mi away)
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Located in Laurel, MD / 166 miles away from Chesapeake, VA
CARFAX One-Owner. This 2021 Ruby Flare Pearl Toyota Highlander XLE AWD is well equipped and includes these features and benefits:. 8-Speed Automatic...
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: 5TDHZRBHXMS124487
Stock: MH10430
Certified Pre-Owned: No
Listed since: 05-13-2025 - $24,750great price$1,694 below market
- 99,693 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Easton Toyota (139 mi away)
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Located in Easton, MD / 139 miles away from Chesapeake, VA
2021 Toyota Highlander LE 2021 Toyota Highlander LE in Blizzard Pearl, Please call 410-822-8000 with any equipment or availability questions!, Schedul...
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: 5TDBZRBH5MS089928
Stock: KET250059A
Certified Pre-Owned: No
Listed since: 05-05-2025 - New Listing$44,841great price$2,512 below market
- 27,794 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Koons Annapolis Toyota (156 mi away)
Close
Located in Annapolis, MD / 156 miles away from Chesapeake, VA
AWD, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated front seats, Heat...
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: 5TDKDRBH9PS000249
Stock: KATP230100A
Certified Pre-Owned: No
Listed since: 05-24-2025 - Price Drop$32,990good price$2,785 below market
- 35,618 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 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,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satelli...
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: 5TDKDRBH6PS514219
Stock: PS514219P
Certified Pre-Owned: No - Price Drop$33,500fair price$826 below market
- 34,771 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Honda of Tysons Corner (161 mi away)
Close
Located in Vienna, VA / 161 miles away from Chesapeake, VA
ONE OWNER, CLEAN CARFAX, FACTORY WARRENTY, BACKUP CAMERA / REAR VIEW CAMERA / REVERSE CAMERA, ADAPTIVE CRUISE CONTROL / ACC / DYNAMIC RADAR CRUISE CON...
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: 5TDGZRBH5MS548283
Stock: A548283
Certified Pre-Owned: No
Listed since: 04-14-2025 - Price Drop$30,500fair price$792 below market
- 49,540 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Ourisman Toyota 40 (187 mi away)
Close
Located in Edgewood, MD / 187 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. 22/29 City/Highway MPG This 2023 Wind Chill Pearl Toyota Highlander L FWD is well equipped and includes these features...
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: 5TDKDRAH3PS036813
Stock: R2601
Certified Pre-Owned: No
Listed since: 04-18-2025 - $35,999good price$1,053 below market
- 53,853 miles
- No accidents, 1 owner, personal use only
- 7 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: 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: 5TDKDRAH1PS003695
Stock: 7VDN1H
Certified Pre-Owned: No
Listed since: 04-16-2025 - Price Drop$30,497good price$2,304 below market
- 35,825 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
Close
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: 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: 5TDKDRAH9PS023581
Stock: RPS023581
Certified Pre-Owned: No
Listed since: 04-02-2025 - New Listing$33,890fair price$389 below market
- 26,062 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Passport Toyota (150 mi away)
Close
Located in Suitland, MD / 150 miles away from Chesapeake, VA
Certified. 2023 Toyota Highlander LE Wind Chill Pearl FWD AutomaticToyota Gold Certified, Blind Spot Monitor, Backup Camera, Bluetooth, USB Ports, A...
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: 5TDKDRAH5PS021990
Stock: 27684A
Certified Pre-Owned: Yes
Listed since: 04-26-2025 - Price Drop$35,999fair price$977 below market
- 10,727 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Country Chevrolet (162 mi away)
Close
Located in Warrenton, VA / 162 miles away from Chesapeake, VA
2023 Toyota Highlander L Celestial Silver Metallic FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic ABS brakes, Active Cruis...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS526294
Stock: 45819B
Certified Pre-Owned: No
Listed since: 03-24-2025 - Price Drop$34,000fair price$428 below market
- 42,678 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (150 mi away)
Close
Located in Suitland, MD / 150 miles away from Chesapeake, VA
Certified. 2023 Toyota Highlander LE Midnight Black Metallic AWD AutomaticToyota Gold Certified, New Tires, Blind Spot Monitor, Backup Camera, Bluet...
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: 5TDKDRBH5PS033541
Stock: B8756
Certified Pre-Owned: Yes
Listed since: 04-25-2025
Showing 85 - 105 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 LE 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $24,683 | $26,499 | $28,549 |
| Clean | $24,374 | $26,140 | $28,131 |
| Average | $23,858 | $25,540 | $27,435 |
| Rough | $23,188 | $24,760 | $26,530 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $32,285. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 52,209. Based on the average mileage of 52,209 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 $23,858.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.