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2,079 listings
- $28,695great price$2,368 below market
- 68,052 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Auto Diamond Sales (88 mi away)
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Located in Richmond, VA / 88 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: 5TDDZRBH7LS056355
Stock: 056355
Certified Pre-Owned: No - $37,000fair price$795 above market
- 39,972 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota of Woodbridge (144 mi away)
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Located in Woodbridge, VA / 144 miles away from Chesapeake, VA
POWER MOONROOF / SUNROOF / POWER TILT SLIDING ROOF, BLIS / BLIND SPOT MONITORING / BLIND SIDE ALERT, DYNAMIC RADAR CRUISE CONTROL / ADAPTIVE CRUISE 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: 5TDGZRBHXNS223243
Stock: A223243
Certified Pre-Owned: No
Listed since: 07-21-2025 - $37,995fair price$126 below market
- 35,570 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Battlefield Toyota (155 mi away)
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Located in Culpeper, VA / 155 miles away from Chesapeake, VA
++TOYOTA CERTIFIED EXTENDED WARRANTY INCLUDED++ ++1-OWNER++ 4 BRAND NEW TIRES++ XLE PACKAGE++ AWD++ 2022 Toyota Highlander XLE 3.5L V6 DOHC 20/27 City...
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: 5TDGZRBH9NS227719
Stock: P5543
Certified Pre-Owned: Yes
Listed since: 07-19-2025 - $33,900good price$834 below market
- 51,622 miles
- 1 accident, 1 owner, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Chrysler Dodge Jeep Ram Fiat of Baltimore (178 mi away)
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Located in Baltimore, MD / 178 miles away from Chesapeake, VA
CARFAX One-Owner. This 2022 Midnight Black Toyota Highlander XLE AWD is well equipped and includes these features and benefits:. *** Back Up Camera ...
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: 5TDGZRBH5NS224705
Stock: R4652
Certified Pre-Owned: No
Listed since: 06-05-2025 - New Listing$33,990fair price$630 above market
- 46,825 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Carvana - Washington DC (129 mi away)
- Home delivery*
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Located in Washington, DC / 129 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/29 Highway)
Listing Information:
VIN: 5TDGZRAH8NS116662
Stock: 2003834667
Certified Pre-Owned: No
Listed since: 06-26-2025 - $36,211fair price$536 above market
- 47,593 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Toyota of Bowie (156 mi away)
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Located in Bowie, MD / 156 miles away from Chesapeake, VA
Magnetic Gray Metallic exterior and BLACK interior. Heated Seats, Sunroof, 3rd Row Seat, Alloy Wheels, Quad Seats, All Wheel Drive, Power Liftgate. ...
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: 5TDGZRBH6NS593346
Stock: NS593346
Certified Pre-Owned: No
Listed since: 07-03-2025 - New Listing
- 69,915 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 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: 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: 5TDFZRBH7LS046482
Stock: 2003816534
Certified Pre-Owned: No
Listed since: 06-14-2025 - New Listing$34,998fair price$543 above market
- 48,543 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax Raleigh (151 mi away)
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Located in Raleigh, NC / 151 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/29 Highway)
Listing Information:
VIN: 5TDGZRAH5NS556578
Stock: 25830765
Certified Pre-Owned: No - Price Drop$35,481fair price$609 below market
- 43,302 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Nationwide Nissan (188 mi away)
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Located in Timonium, MD / 188 miles away from Chesapeake, VA
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: 5TDHZRBH1NS576720
Stock: 16394P
Certified Pre-Owned: No
Listed since: 04-28-2025 - New Listing$39,163fair price$375 above market
- 20,053 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
Recent Arrival! 2022 Toyota Highlander XLE Magnetic Gray Metallic AWD AutomaticSunroof/Moonroof, Heated Seats, Blind Spot Monitor, Backup Camera, Bl...
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: 5TDHZRBH0NS584811
Stock: T584811P
Certified Pre-Owned: No
Listed since: 07-23-2025 - New Listing$36,000good price$884 below market
- 26,514 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Tysons Chrysler Dodge Jeep Ram (161 mi away)
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Located in Vienna, VA / 161 miles away from Chesapeake, VA
Recent Arrival! 2022 Toyota Highlander XLE AWD RedAWD.Odometer is 16821 miles below market average! Priced below KBB Fair Purchase Price!Vehicl...
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: 5TDGZRBH2NS221101
Stock: KTJS220028A
Certified Pre-Owned: No
Listed since: 07-29-2025 - $23,999fair price$376 above market
- 131,150 miles
- 2 accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Paragon Automotive (9 mi away)
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Located in Virginia Beach, VA / 9 miles away from Chesapeake, VA
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: 5TDGZRAH2LS501664
Stock: 1761
Certified Pre-Owned: No - New Listing$31,990fair price$86 below market
- 69,044 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Baltimore (185 mi away)
- Home delivery*
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Located in Baltimore, MD / 185 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: 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: 5TDGZRBH8NS200351
Stock: 2003743479
Certified Pre-Owned: No
Listed since: 05-29-2025 - Price Drop$35,949fair price$123 above market
- 39,916 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Annapolis Toyota (156 mi away)
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Located in Annapolis, MD / 156 miles away from Chesapeake, VA
**ONE OWNER CARFAX**, **LEATHER SEATING**, **POWER MOONROOF**, **AWD**, **POWER LIFTGATE**, **BLUETOOTH**, **BACK-UP CAMERA**, **3RD ROW SEATING**, **...
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: 5TDGZRBH3NS238571
Stock: KATP220247
Certified Pre-Owned: No
Listed since: 07-24-2025 - New Listing$25,750fair price$48 above market
- 82,881 miles
- No accidents, 2 owners, corporate fleet vehicle
- 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
Recent Arrival! 2020 Toyota Highlander LE 2020 Toyota Highlander LE in Blizzard Pearl, Please call 410-822-8000 with any equipment or availability que...
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: 5TDBZRBH1LS501843
Stock: KETP200155
Certified Pre-Owned: No
Listed since: 07-26-2025 - Price Drop$30,999great price$5,579 below market
- 53,756 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Southern Chrysler Dodge Jeep RAM Chesapeake (14 mi away)
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Located in Chesapeake, VA / 14 miles away from Chesapeake, VA
Certified. Celestial Silver Metallic 2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic FWD SUNROOF/MOO...
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: 5TDKDRAH8PS504793
Stock: YP10777
Certified Pre-Owned: No
Listed since: 06-16-2025 - Price Drop$37,207fair price$16 above market
- 28,292 miles
- 2 accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Annapolis Toyota (156 mi away)
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Located in Annapolis, MD / 156 miles away from Chesapeake, VA
**ONE OWNER CARFAX**, **POWER MOONROOF**, **AWD**, **POWER LIFTGATE**, **BLUETOOTH**, **BACK-UP CAMERA**, **3RD ROW SEATING**, **BLIND SPOT MONITORING...
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: 5TDGZRBH2NS572395
Stock: KATP220209
Certified Pre-Owned: No
Listed since: 07-14-2025 - Price Drop
- 90,262 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Autova (167 mi away)
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Located in Madison Heights, VA / 167 miles away from Chesapeake, VA
Experience the Perfect Blend of Power and Comfort with the 2022 Toyota Highlander LEDiscover the 2022 Toyota Highlander LE, a used gem designed for...
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: 5TDBZRBH5NS587578
Stock: 16022
Certified Pre-Owned: No
Listed since: 06-19-2025 - New Listing$29,900fair price$798 below market
- 65,622 miles
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (151 mi away)
- Home delivery*
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Located in Springfield, VA / 151 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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH2LS513526
Stock: LS513526P
Certified Pre-Owned: No - 43,400 miles
- Frame damage reported, 3 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Alpha Motor Sports (127 mi away)
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Located in Fredericksburg, VA / 127 miles away from Chesapeake, VA
** OVER 30,000 VEHICLES SOLD, TWO LOCATION TO SERVE YOU, 400+ VEHICLES IN STOCK, visit www.AlphaMS.com to view our inventory, BEST PRICES IN TOWN **NA...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBHXNS240737
Stock: S240737
Certified Pre-Owned: No- Price Drop
- 15,582 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Arlington Toyota (157 mi away)
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Located in Arlington, VA / 157 miles away from Chesapeake, VA
2022 Toyota Highlander XLE 3rd row seats: split-bench, ABS brakes, Apple CarPlay/Android Auto, Automatic temperature control, Exterior Parking Camera ...
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: 5TDGZRBH2NS214438
Stock: KTWP220870
Certified Pre-Owned: No
Listed since: 07-14-2025
Showing 106 - 126 out of 2,079 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 2020 Toyota Highlander in Chesapeake, VA Values
Estimated values
2020 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $29,917 | $32,414 | $34,819 |
| Clean | $29,142 | $31,565 | $33,896 |
| Average | $27,852 | $30,149 | $32,356 |
| Rough | $26,173 | $28,309 | $30,355 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $33,528. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 53,232. Based on the average mileage of 53,232 for used 2020 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 2020 in Chesapeake, Virginia to be $27,852.
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