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2,159 listings
- Price Drop$30,998good price$1,499 below market
- 50,260 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Hamilton, NJ / 256 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,Keyless Start,Lane Kee...
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: 5TDKDRAH4PS007935
Stock: PS007935U
Certified Pre-Owned: No - New Listing$28,590fair price
- 93,665 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 1,195 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: 5TDKDRAH9PS016632
Stock: 2003773220
Certified Pre-Owned: No
Listed since: 06-06-2025 - Price Drop$31,259fair price$1,488 below market
- 45,900 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Troy, MI / 546 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,WiFi Hotspot,Pow...
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: 5TDKDRAH7PS040637
Stock: PS040637C
Certified Pre-Owned: No - Price Drop$33,391good price$938 below market
- 51,100 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- Ourisman Fairfax Toyota (158 mi away)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
How about this great vehicle! It offers the latest in technological innovation and style. Turbocharger technology provides forced air induction, enhan...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH2PS027276
Stock: 233627A
Certified Pre-Owned: No
Listed since: 05-02-2025 - 40,464 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Costa Mesa, CA / 2,344 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS507581
Stock: 27329224
Certified Pre-Owned: No- $36,572fair price$56 above market
- 43,484 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Cary Imports (157 mi away)
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Located in Cary, NC / 157 miles away from Chesapeake, VA
2023 TOYOTA HIGHLANDER / CLEAN CARFAX / NO ACCIDENTS / 1 OWNER / SPOTLESS CAR / SHOWS LIKE NEW / FACTORY RUBBER FLOOR MATS / ONLY 43K MILES / FWD / Ca...
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: 5TDKDRAH3PS524062
Stock: 1030
Certified Pre-Owned: No
Listed since: 03-01-2025 - $29,333fair price
- 77,416 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 1,189 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Satellite Radio,Tur...
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: 5TDKDRAH2PS504904
Stock: PS504904P
Certified Pre-Owned: No - $28,000fair price$274 below market
- 67,648 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Chevrolet of Rockville (167 mi away)
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Located in Rockville, MD / 167 miles away from Chesapeake, VA
Recent Arrival! This 2021 Black Toyota Highlander LE AWD is well equipped and includes these features and benefits:.20/27 City/Highway MPG Bluetooth, ...
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: 5TDBZRBH1MS114453
Stock: 5141EA
Certified Pre-Owned: No
Listed since: 05-30-2025 - $37,850fair price$376 above market
- 61,424 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Sanford Imports (187 mi away)
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Located in Sandford, NC / 187 miles away from Chesapeake, VA
2021 Toyota Highlander Platinum Midnight Black Metallic Carfax Accident Free, Leather Seats, Navigation, Bluetooth, Collision Warning Alert System, Co...
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: 5TDFZRBH2MS085191
Stock: 7006017
Certified Pre-Owned: No
Listed since: 05-23-2025 - New Listing
- 51,739 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Jacksonville, FL / 538 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: 5TDKDRAH7PS036975
Stock: 8F3G20
Certified Pre-Owned: No
Listed since: 05-29-2025 - $36,987fair price$736 above market
- 52,368 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Priority Lexus Newport News (32 mi away)
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Located in Newport News, VA / 32 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS014341
Stock: PLN21009
Certified Pre-Owned: No
Listed since: 04-30-2025 - Price Drop$34,583fair price$710 above market
- 72,678 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Crossroads Ford of Dunn-Benson (166 mi away)
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Located in Dunn, NC / 166 miles away from Chesapeake, VA
1 Owner, AWD, 3rd row seats: split-bench, 6 Speakers, AM/FM radio: SiriusXM, Apple CarPlay/Android Auto, Automatic temperature control, Exterior Parki...
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: 5TDLZRBHXMS082686
Stock: U649A
Certified Pre-Owned: No
Listed since: 05-10-2025 - $39,999fair price$655 above market
- 38,150 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Metairie, LA / 928 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: 5TDKDRBH8PS508728
Stock: 8DDX77
Certified Pre-Owned: No
Listed since: 05-19-2025 - Price Drop
- 39,094 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Trust Auto (192 mi away)
Close
Located in Sykesville, MD / 192 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 - Price Drop$36,982fair price$308 below market
- 50,550 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Pocatello, ID / 1,952 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats...
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: 5TDKDRBH0PS500574
Stock: PS500574T
Certified Pre-Owned: No - New Listing$33,000fair price$278 above market
- 51,759 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 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. Priced below KBB Fair Purchase Price! *Full Family Plan* INCLUDES OIL CHANGES FOR LIFE!, Still Under Factory Powertrai...
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: 5TDKDRAHXPS005722
Stock: PS005722P
Certified Pre-Owned: No
Listed since: 05-15-2025 - $31,999fair price$640 above market
- 59,876 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Waukesha, WI / 767 miles away from Chesapeake, VA
This vehicle passed a rigorous inspection by an ASE-Certified technician and is backed by a 12-Month/12,000 Mile Limited Powertrain Warranty(1). We of...
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: 5TDKDRAH6PS020895
Stock: 8DM454
Certified Pre-Owned: No
Listed since: 05-27-2025 - $37,649fair price$342 below market
- 50,744 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Elmwood Park, NJ / 309 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: 5TDKDRBH5PS501414
Stock: 8DYND9
Certified Pre-Owned: No
Listed since: 02-27-2025 - $31,995fair price$318 above market
- 77,712 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Imperial Highline (157 mi away)
Close
Located in Manassas, VA / 157 miles away from Chesapeake, VA
LOADED WITH VALUE! Comes equipped with: Cockpit Red, Leather Seat Trim. This Toyota Highlander also includes Power Driver's Seat, Clock, Climate Contr...
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: 5TDLZRAH9MS051737
Stock: 51737
Certified Pre-Owned: No
Listed since: 04-29-2025 - 57,162 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Crossroads INFINITI of Raleigh (143 mi away)
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Located in Raleigh, NC / 143 miles away from Chesapeake, VA
For More Information Call:Crossroads INFINITI of Raleigh(919)981-5656CARFAX One-Owner. Clean CARFAX. 2021 Toyota HighlanderClean Carfax, One Owner, 20...
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- Price Drop$31,632fair price$645 above market
- 80,008 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Pearson Toyota (34 mi away)
Close
Located in Newport News, VA / 34 miles away from Chesapeake, VA
2023 Toyota Highlander L 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp FWD Magnetic Gray22/29 City/Highway MPGWe offer Market Based Pricing, so...
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: 5TDKDRAH2PS518298
Stock: N8866
Certified Pre-Owned: No
Listed since: 05-14-2025
Showing 337 - 357 out of 2,159 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 LE 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $23,787 | $25,621 | $27,690 |
| Clean | $23,489 | $25,273 | $27,285 |
| Average | $22,992 | $24,693 | $26,610 |
| Rough | $22,347 | $23,939 | $25,732 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $34,158. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 57,771. Based on the average mileage of 57,771 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 $22,992.
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