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2,090 listings
- $19,998great price$2,057 below market
- 141,865 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- CarHub (137 mi away)
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Located in Stafford, VA / 137 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFHXKS600505
Stock: 600505
Certified Pre-Owned: No - New Listing$24,522great price$2,243 below market
- 73,555 miles
- No accidents, 3 owners, personal use
- 8 Seats, 21 City / 27 Hwy MPG
- Capital Chrysler Jeep Dodge Ram (149 mi away)
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Located in Garner, NC / 149 miles away from Chesapeake, VA
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH4KS569403
Stock: GAC11780
Certified Pre-Owned: No
Listed since: 04-03-2025 - $25,267great price$2,606 below market
- 75,085 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Lexus of Towson (186 mi away)
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Located in Towson, MD / 186 miles away from Chesapeake, VA
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH4KS579487
Stock: T2762AAA
Certified Pre-Owned: No
Listed since: 05-12-2025 - Price Drop$23,000great price$2,428 below market
- 114,434 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Antwerpen Toyota (175 mi away)
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Located in Clarksville, MD / 175 miles away from Chesapeake, VA
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: 5TDBZRBH3MS132081
Stock: 1848P
Certified Pre-Owned: No
Listed since: 04-01-2025 - New Listing$27,998great price
- 91,286 miles
- 2 accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Killeen, TX / 1,289 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: 5TDLZRBH5MS068596
Stock: 27072872
Certified Pre-Owned: No - New Listing$33,998good price$2,448 below market
- 19,114 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax Virginia Beach (10 mi away)
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Located in Virginia Beach, VA / 10 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH6PS513251
Stock: 27487087
Certified Pre-Owned: No - Price Drop$32,990good price$2,914 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 - $44,841great price$2,316 below market
- 27,794 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Koons Annapolis Toyota (155 mi away)
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Located in Annapolis, MD / 155 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$23,195great price$2,151 below market
- 128,387 miles
- 1 accident, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in North Brunswick, NJ / 273 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
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: 5TDGZRAH1MS070221
Stock: SS044301A
Certified Pre-Owned: No - New Listing$33,827fair price$532 below market
- 26,062 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Passport Toyota (149 mi away)
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Located in Suitland, MD / 149 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$35,500good price$2,084 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 AutomaticABS brakes, Active Cruise...
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$30,000fair price$1,281 below market
- 49,540 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Ourisman Toyota 40 (186 mi away)
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Located in Edgewood, MD / 186 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$30,197good price$2,639 below market
- 35,825 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (156 mi away)
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Located in Cary, NC / 156 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$29,771great price$2,156 below market
- 63,156 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Chantilly Kia (164 mi away)
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Located in Chantilly, VA / 164 miles away from Chesapeake, VA
Warranty Available. 20/27 City/Highway MPG2021 White Toyota Highlander XLE 4D Sport Utility AWD 3.5L V6 DOHC 8-Speed AutomaticAt Ourisman Chantilly Ki...
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: 5TDGZRBHXMS138160
Stock: BK24669A
Certified Pre-Owned: No
Listed since: 05-31-2025 - Price Drop$27,871great price$2,650 below market
- 83,750 miles
- 1 accident, 4 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Billings, MT / 1,779 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
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: 5TDGZRBH8MS074409
Stock: 53105
Certified Pre-Owned: No - $25,575good price$2,298 below market
- 81,559 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- BMW of Catonsville (179 mi away)
- Five Star Dealer
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Located in Baltimore, MD / 179 miles away from Chesapeake, VA
AWD.Recent Arrival! CARFAX One-Owner. Clean CARFAX.*Your additional costs are sales tax, tag and title fees for the state in which the vehicle will be...
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFHXKS944641
Stock: 4P2659
Certified Pre-Owned: No
Listed since: 05-21-2025 - Price Drop$34,000fair price$303 below market
- 42,678 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (149 mi away)
Close
Located in Suitland, MD / 149 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$36,900fair price$546 below 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 - $22,000good price$1,691 below market
- 121,621 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Koons Tysons Chevy GMC (160 mi away)
Close
Located in Vienna, VA / 160 miles away from Chesapeake, VA
AWD, ABS brakes, Active Cruise Control, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seats, Heated fron...
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH5KS589820
Stock: 0250875B
Certified Pre-Owned: No
Listed since: 05-22-2025 - New Listing$33,998good price$1,459 below market
- 70,840 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Medford, OR / 2,479 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Navigatio...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH9MS061786
Stock: 61786A
Certified Pre-Owned: No - $40,594good price$1,996 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
Showing 169 - 189 out of 2,090 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Couldn’t be happier!
S Curry, 01/02/2021
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
I’ve been eyeing the Highlander since they redesigned it in 2020. I opted for the Limited AWD trim with the optional 12 inch screen and bench seats. I am completely blown away on how amazing it is to drive the Highlander. Visibility is great but with the bigger screen you also get birds eye view which will definitely help assess your surroundings. The safety features are awesome and the … little things like intuitive climate control are nice. I was worried about access into the third row and comfort but my 12 year old is happy with it. The middle row does slide up giving more leg room to the third row. I came from a minivan so I am used to a lot of cargo room and low entry. If you will be using the third row consistently I recommend getting the cross bars and on roof cargo storage to maximize what you can carry, and if you are transporting smaller kids/adults the step up may be just slightly too high for them but running boards can be installed.
Used 2019 Toyota Highlander in Chesapeake, VA Values
Estimated values
2019 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $25,042 | $27,708 | $30,078 |
| Clean | $24,279 | $26,856 | $29,145 |
| Average | $23,007 | $25,436 | $27,591 |
| Rough | $21,354 | $23,591 | $25,570 |
The average list price of a used 2019 Toyota Highlander in Chesapeake, Virginia is $30,288. The average mileage on a used Toyota Highlander 2019 for sale in Chesapeake, Virginia is 64,651. Based on the average mileage of 64,651 for used 2019 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 2019 in Chesapeake, Virginia to be $23,007.
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