Skip to FiltersReport abuse
1,877 listings
- $43,000fair price$331 above market
- 35,932 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Ourisman Toyota of Woodbridge (144 mi away)
Close
Located in Woodbridge, VA / 144 miles away from Chesapeake, VA
PANORAMIC ROOF / DUAL SUNROOFS / TWIN PANEL MOONROOF, POWER MOONROOF / SUNROOF / POWER TILT SLIDING ROOF, NAVIGATION / GPS / NAV, BLIS / BLIND SPOT MO...
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: 5TDFZRAH0NS118689
Stock: A118689
Certified Pre-Owned: No
Listed since: 04-28-2025 - $35,998fair price$621 above market
- 28,502 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from OR to VA*
Close
Located in Salem, OR / 2,473 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: 5TDHZRBH0LS516764
Stock: 27271592
Certified Pre-Owned: No - $32,000fair price$57 below market
- 40,808 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Silver Spring (166 mi away)
Close
Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
2022 Toyota Highlander LE Recent Arrival! CARFAX One-Owner.Blue AWD. AWD 3.5L V6 DOHC 8-Speed Automatic Priced below KBB Fair Purchase Price! 20/27 ...
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: 5TDBZRBH0NS249974
Stock: E1A0516
Certified Pre-Owned: No
Listed since: 05-22-2025 - $36,704fair price$256 above market
- 44,399 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 27 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,Brake Assist,Heated Seats,Lane Keeping Assist...
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: 5TDGZRBH0NS231660
Stock: NS231660P
Certified Pre-Owned: No - $44,000fair price$143 above market
- 30,217 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota of Woodbridge (144 mi away)
Close
Located in Woodbridge, VA / 144 miles away from Chesapeake, VA
PANORAMIC ROOF / DUAL SUNROOFS / TWIN PANEL MOONROOF, POWER MOONROOF / SUNROOF / POWER TILT SLIDING ROOF, NAVIGATION / GPS / NAV, BLIS / BLIND SPOT MO...
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: 5TDFZRBH0NS227507
Stock: A227507
Certified Pre-Owned: No
Listed since: 05-16-2025 - Price Drop$22,400fair price$430 below market
- 94,334 miles
- 2 accidents, 2 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Marine Chevrolet (149 mi away)
Close
Located in Jacksonville, NC / 149 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH2JS835981
Stock: ST1291AT
Certified Pre-Owned: No
Listed since: 05-16-2025 - New Listing$31,997fair price$607 below market
- 79,006 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Hanna Imports (148 mi away)
Close
Located in Raleigh, NC / 148 miles away from Chesapeake, VA
*Carfax Accident Free*, Leather Seats, Bluetooth, *Multi Point Inspection*, Highlander XLE, Apple CarPlay/Android Auto, Heated Front Bucket Seats, Pow...
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: 5TDGZRAH3NS539472
Stock: 3021617A
Certified Pre-Owned: No
Listed since: 05-28-2025 - $32,987fair price$263 above market
- 50,214 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Gloucester Toyota (48 mi away)
Close
Located in Gloucester, VA / 48 miles away from Chesapeake, VA
Come see this 2020 Toyota Highlander XLE while we still have it in stock! This Toyota Highlander Is Competitively Priced with These Options Window Gri...
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: 5TDHZRBH4LS010001
Stock: P3811A
Certified Pre-Owned: No
Listed since: 05-25-2025 - $34,500good price$1,176 below market
- 43,014 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota of Woodbridge (144 mi away)
Close
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: 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: 5TDGZRBH6NS248365
Stock: A248365
Certified Pre-Owned: No
Listed since: 04-30-2025 - $27,303fair price$524 below market
- 83,810 miles
- No accidents, 3 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Ourisman Fairfax Toyota (158 mi away)
Close
Located in Fairfax, VA / 158 miles away from Chesapeake, VA
Silver 2020 Toyota Highlander XLE FWD 8-Speed Automatic 3.5L V6 DOHC CERTIFIED 7 YEAR/ 100,000 MILE WARRANTY.Our best available bank and credit un...
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: 5TDGZRAH5LS028133
Stock: 13140PP
Certified Pre-Owned: No
Listed since: 05-23-2025 - $43,895fair price$683 below market
- 29,240 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Fitzgerald Toyota Gaithersburg (176 mi away)
Close
Located in Gaithersburg, MD / 176 miles away from Chesapeake, VA
This vehicle won't be on the lot long! Pure practicality in a stylish package. It includes power seats, leather upholstery, heated and ventilated seat...
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: 5TDFZRBH9NS230244
Stock: 086809A
Certified Pre-Owned: Yes
Listed since: 05-03-2025 - $28,500fair price$159 below market
- 71,220 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- i.g. Burton Toyota of Dover (174 mi away)
Close
Located in Dover, DE / 174 miles away from Chesapeake, VA
TOYOTA CERTIFIED, ONE OWNER, CLEAN CARFAX, NAVIGATION, SUNROOF, HEATED & COOLED LEATHER SEATS, JBL PREMIUM AUDIO, POWER LIFTGATE, BACKUP CAMERA, AWD!!...
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: 5TDDZRFH4JS815955
Stock: T251403A
Certified Pre-Owned: Yes
Listed since: 05-21-2025 - Price Drop$31,388fair price$535 below market
- 65,935 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Anderson Honda (190 mi away)
Close
Located in Cockeysville, MD / 190 miles away from Chesapeake, VA
Ruby Flare Pearl exterior and Harvest Beige interior. Heated Leather Seats, 3rd Row Seat, Navigation, Sunroof, Alloy Wheels, Captains Chairs, All Whee...
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: 5TDDZRBH1LS004669
Stock: D7574A
Certified Pre-Owned: No
Listed since: 03-18-2025 - Price Drop$36,595good price$1,219 below market
- 37,855 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Reynolds Subaru (147 mi away)
Close
Located in Orange, VA / 147 miles away from Chesapeake, VA
CARFAX One-Owner. Silver 2022 Toyota Highlander XSE AWD 8-Speed Automatic 3.5L V6 DOHC **SUNROOF/MOONROOF**, **LEATHER**, **ONE OWNER**, **STILL UNDER...
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: 5TDLZRBH5NS208406
Stock: 38892P
Certified Pre-Owned: No
Listed since: 05-03-2025 - $34,597fair price$10 above market
- 55,186 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Radley Acura (154 mi away)
Close
Located in Falls Church, VA / 154 miles away from Chesapeake, VA
CARFAX One-Owner. Recent Arrival! 20/27 City/Highway MPG Priced below KBB Fair Purchase Price!3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel D...
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: 5TDGZRBH4NS583480
Stock: CP2229
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$30,142fair price$285 above market
- 115,520 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Greenville Nissan (104 mi away)
Close
Located in Greenville, NC / 104 miles away from Chesapeake, VA
11 Speakers, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, App...
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: 5TDYZRAH7NS101042
Stock: U18725
Certified Pre-Owned: No
Listed since: 03-05-2025 - New Listing$36,998fair price$508 above market
- 38,661 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Brandywine (139 mi away)
Close
Located in Brandywine, MD / 139 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH8NS248383
Stock: 26652157
Certified Pre-Owned: No - $25,989good price$813 below market
- 69,057 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Eatontown, NJ / 273 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping ...
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: 5TDBZRBH1LS514642
Stock: LS514642P
Certified Pre-Owned: No - $30,120fair price$587 above market
- 85,286 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Bayside Toyota (128 mi away)
Close
Located in Prince Frederick, MD / 128 miles away from Chesapeake, VA
Need an SUV that can haul your kids, your gear, and your dignity all without breaking a sweat? The 2020 Toyota Highlander XLE AWD is like your favorit...
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: 5TDHZRBH1LS504042
Stock: LS504042
Certified Pre-Owned: No
Listed since: 04-19-2025 - $29,209fair price
- 89,029 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 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,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
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: 5TDGZRBH5LS013310
Stock: LS013310P
Certified Pre-Owned: No - $34,500fair price$701 above market
- 38,459 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lexus of Silver Spring (166 mi away)
Close
Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
2020 Toyota Highlander XLECelestial Silver AWD, 18 Machined Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speaker...
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: 5TDGZRBH5LS512916
Stock: P1D1566
Certified Pre-Owned: No
Listed since: 04-19-2025
Showing 190 - 210 out of 1,877 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
"Some Adjustment Needed"
Bill, 01/11/2020
2020 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 8A)
Test drove the 2020 Limited. V-6 engine was responsive and ride was very quiet. Very good standard technology and driving safety packages. Interior had quality materials and good fit and finish. Second row captains chair seats are comfortable with plenty of room behind first row, third row seats useless except for small children which you would want in second row. Big disappointment … was drivers seat height adjustment; you better be 5'4" or above to have clear visibility over steering wheel and dash. Also, passenger seat has NO height adjustment; passengers 6'3" or above will be at or close to the ceiling. Except for the lack of adequate front seat height adjustments, I loved the car.
Used 2022 Toyota Highlander in Chesapeake, VA Values
Estimated values
2022 Toyota Highlander Platinum 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $31,416 | $33,890 | $36,474 |
| Clean | $30,888 | $33,295 | $35,806 |
| Average | $30,009 | $32,303 | $34,691 |
| Rough | $28,866 | $31,013 | $33,243 |
The average list price of a used 2022 Toyota Highlander in Chesapeake, Virginia is $33,468. The average mileage on a used Toyota Highlander 2022 for sale in Chesapeake, Virginia is 58,366. Based on the average mileage of 58,366 for used 2022 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 2022 in Chesapeake, Virginia to be $30,009.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.