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2,061 listings
- Price Drop$34,071great price$5,866 below market
- 40,946 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
Certified. 2023 Toyota Highlander LE Magnetic Gray Metallic AWD AutomaticToyota Gold Certified, New Tires, Blind Spot Monitor, Backup Camera, Blueto...
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: 5TDKDRBH7PS017874
Stock: B8784
Certified Pre-Owned: Yes
Listed since: 05-09-2025 - Price Drop$29,497great price$3,835 below market
- 30,521 miles
- No accidents, 1 owner, rental vehicle
- 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: 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: 5TDKDRAH4PS032107
Stock: RPS032107
Certified Pre-Owned: No
Listed since: 04-01-2025 - Price Drop$29,990great price$2,727 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$3,497 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)
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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 - Price Drop$35,995great price$5,204 below market
- 46,732 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Platinum Auto Sales of Arlington Virginia (156 mi away)
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Located in Arlington, VA / 156 miles away from Chesapeake, VA
Non-smoker owner, Vehicle Runs Well, Smooth ride, All records in possession, Regularly maintained, Lots of storage, Arctic cold a/c, No pets, Seats as...
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: 5TDKDRBH4PS507222
Stock: 507222
Certified Pre-Owned: No - Price Drop$29,397great price$3,344 below market
- 37,671 miles
- No accidents, 1 owner, rental vehicle
- 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: 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 - $33,975great price$3,308 below market
- 46,150 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Capital Ford (144 mi away)
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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 - Price Drop$30,500fair price$935 below market
- 49,540 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Ourisman Toyota 40 (187 mi away)
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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 - Price Drop$30,497good price$2,395 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 - Price Drop$33,550good price$2,197 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 - $35,999fair price$576 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*
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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: 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 - $30,997good price$2,368 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 - $32,999good price$1,412 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 - Price Drop$35,999fair price$858 below market
- 10,727 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Country Chevrolet (162 mi away)
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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$40,594good price$1,403 below market
- 18,410 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Lynchburg Nissan (172 mi away)
Close
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 - Price Drop$39,990fair price$8 below market
- 15,693 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
Close
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: 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: 5TDKDRBH8PS005345
Stock: 2003648907
Certified Pre-Owned: No
Listed since: 05-06-2025 - $36,990good price$1,474 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 - $34,000fair price$784 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 - Price Drop$33,397good price$1,462 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)
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: 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 - $40,998fair price$449 below market
- 17,671 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax Harrisonburg (187 mi away)
Close
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 - New Listing$44,841good price$2,438 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
Showing 1 - 21 out of 2,061 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Love the vehicle, Infotainment is unusable
bbells, 04/16/2023
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A)
Love the gas mileage, 30+mpg in eco mode. Towing capacity. Comfort. Nice vehicle except the "drive connect" app advertisement makes the entertainment system unusable. It will lock up the system for 1 to 10 minutes so no music, no google maps, no phone, nothing, until it decides to clear itself. Toyota says you can pay $200 a year to remove the advertisement by subscribing to drive … connect. This makes it the definition of ransomware. But there is nothing in the app I need or want. Neither ToyotaUSA, their tech department, or the dealer can fix it. I will either be selling the vehicle or replacing the entertainment system when the free trial of drive connect ends in a couple months. For those of us who use their phone for maps, texts or communication the system makes the vehicle unusable. Update: Can't put in different infotainment system, it is integrated into the vehicle. Toyota gave me a free trial of drive connect. Unfortunately anytime i am in an area without internet the display is locked up asking for a password. Can't enter a password until i get into an internet area, then go s back to asking for a password when i leave it. Worthless and unusable. Toyota wouldn't fix it. After 7 months they bought it back from me. Last Toyota.
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 | $33,460 | $35,152 | $37,058 |
| Clean | $33,041 | $34,675 | $36,515 |
| Average | $32,342 | $33,879 | $35,612 |
| Rough | $31,434 | $32,845 | $34,438 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $34,440. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 35,587. Based on the average mileage of 35,587 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 $32,342.
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