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2,076 listings
- Price Drop$28,000good price$1,855 below market
- 43,704 miles
- 1 accident, 2 owners, personal use only
- 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: 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: 5TDJZRFH7KS732329
Stock: T2167AA
Certified Pre-Owned: No
Listed since: 04-29-2025 - $37,200fair price$446 above market
- 41,538 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lindsay Manassas Chrysler Dodge Jeep Ram (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
*WELL MAINTAINED*, POWER SUNROOF / SUNROOF / POWER TILT SLIDING ROOF, APPLE CARPLAY/ANDROID AUTO, BLUETOOTH, PUSH-BUTTON START, WIRELESS CHARGING, 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDLZRBH8MS074151
Stock: MP8945A
Certified Pre-Owned: No
Listed since: 05-15-2025 - $18,795fair price$362 below market
- 153,237 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Olympia Pre-Owned Auto (149 mi away)
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Located in Raleigh, 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH8MS044441
Stock: 044441
Certified Pre-Owned: No - New Listing$27,500fair price$528 below market
- 67,640 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Chevrolet of Rockville (168 mi away)
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Located in Rockville, MD / 168 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: GM5141A
Certified Pre-Owned: No
Listed since: 05-21-2025 - New Listing$30,998fair price$991 below market
- 60,378 miles
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax White Marsh (182 mi away)
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Located in White Marsh, MD / 182 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 Unavailable.
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH8KS923240
Stock: 26925119
Certified Pre-Owned: No - New Listing$37,998fair price$391 above market
- 40,361 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Frederick (173 mi away)
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Located in Gaithersburg, MD / 173 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: 5TDJZRBH2MS158988
Stock: 27191974
Certified Pre-Owned: No - Price Drop$31,251fair price$741 above market
- 65,600 miles
- No accidents, 3 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Honda (154 mi away)
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Located in Bowie, MD / 154 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Moon Dust 8-Speed AutomaticAWD, 3rd row seats: split-bench, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH1MS116306
Stock: 5P2390A
Certified Pre-Owned: No
Listed since: 05-13-2025 - New Listing$32,998fair price$629 above market
- 50,212 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Gaithersburg (194 mi away)
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Located in Frederick, MD / 194 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: 5TDGZRBH1MS531383
Stock: 26736588
Certified Pre-Owned: No - $35,995fair price$28 above market
- 69,961 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Fitzgerald Toyota Gaithersburg (176 mi away)
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Located in Gaithersburg, MD / 176 miles away from Chesapeake, VA
Check out this great low mileage vehicle! Roomy, comfortable, and practical! This model accommodates 7 passengers comfortably, and provides features 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH4MS142703
Stock: EB61729A
Certified Pre-Owned: No
Listed since: 05-06-2025 - 74,069 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Jerry's Toyota (183 mi away)
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Located in Baltimore, MD / 183 miles away from Chesapeake, VA
2021 Toyota Highlander XLE AWD. Only 74,058 miles. Toyota's top selling midsize SUV. Spacious leather trimmed heated seats with 7 pass seating. Huge c...
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: 5TDGZRBH2MS533451
Stock: 251047A
Certified Pre-Owned: No
Listed since: 04-22-2025- Price Drop$31,498fair price$538 above market
- 87,969 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Reidsville Nissan (194 mi away)
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Located in Reidsville, NC / 194 miles away from Chesapeake, VA
CARFAX One-Owner. Blue 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC Fully Detailed, AWD.20/27 City/Highway MPGAwards: * ALG Res...
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: 5TDHZRBH6MS064689
Stock: R13396
Certified Pre-Owned: No
Listed since: 05-13-2025 - 79,746 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- CMA's Honda of Lynchburg (172 mi away)
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Located in Lynchburg, VA / 172 miles away from Chesapeake, VA
Thank you for choosing CMA's Honda of Lynchburg, this Blizzard Pearl 2019 Toyota Highlander Limited is a great choice! Check out the following:No Acci...
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: 5TDYZRFH7KS328476
Stock: 16978A
Certified Pre-Owned: No
Listed since: 04-23-2025- New Listing$37,998fair price$859 above market
- 19,296 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 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: 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: 5TDGZRBH1MS558714
Stock: 27170703
Certified Pre-Owned: No - 16,620 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH4KS626534
Stock: 27431603
Certified Pre-Owned: No- New Listing$33,998fair price$1,230 above market
- 26,681 miles
- 7 Seats, 21 City / 27 Hwy MPG
- CarMax Wilmington (194 mi away)
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Located in Wilmington, NC / 194 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 Unavailable.
Features and Specs:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDYZRFH5KS293727
Stock: 27305058
Certified Pre-Owned: No - Price Drop$25,000fair price$70 above market
- 78,956 miles
- 2 accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Preston Ford of Denton (149 mi away)
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Located in Denton, MD / 149 miles away from Chesapeake, VA
AWD.Founded in 1975, Preston has been providing a friendly, no-hassle car buying experience for more than 45 years. We have been family owned and oper...
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: 5TDBZRFH2KS731612
Stock: H250116A
Certified Pre-Owned: No
Listed since: 03-24-2025 - New Listing$37,250fair price$610 above market
- 61,222 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Tysons Toyota (162 mi away)
- Five Star Dealer
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Located in Vienna, VA / 162 miles away from Chesapeake, VA
AWD.RECALL NOTICE: Some vehicles offered for sale may be subject to unrepaired manufacturer safety recalls. To determine the recall status of a vehi...
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: 5TDFZRBH5MS158490
Stock: 0KW50991
Certified Pre-Owned: No
Listed since: 05-27-2025 - New Listing
- 56,140 miles
- Frame damage reported, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- CarHub (138 mi away)
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Located in Stafford, VA / 138 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH0KS973942
Stock: 973942
Certified Pre-Owned: No - Price Drop$27,774fair price$482 above market
- 71,605 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 26 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
2019 Toyota Highlander XLE Midnight Black Metallic AWD AutomaticNavigation System, Sunroof/Moonroof, Heated Seats, Leather Seats, Blind Spot Monitor...
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: 5TDJZRFH2KS597213
Stock: 28244B
Certified Pre-Owned: No
Listed since: 05-06-2025 - $29,888fair price$735 above market
- 90,038 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Bumble Auto - Ellicott City (179 mi away)
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Located in Ellicott City, MD / 179 miles away from Chesapeake, VA
Delve into a world of exceptional pre-owned vehicles at Bumble Auto, where quality and affordability coalesce. Our varied inventory accommodates diffe...
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: 5TDHZRBH9MS110399
Stock: B3266
Certified Pre-Owned: No - New Listing$39,500fair price$690 above market
- 38,546 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- i.g. Burton Toyota of Dover (174 mi away)
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Located in Dover, DE / 174 miles away from Chesapeake, VA
TOYOTA CERTIFIED, ONE OWNER, CLEAN CARFAX, NAVIGATION, CAR PLAY, HEATED & COOLED LEATHER SEATS, POWER LIFTGATE, SUNROOF, JBL PREMIUM STEREO, BLIND SPO...
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: 5TDDZRBH6MS536503
Stock: TP25112
Certified Pre-Owned: Yes
Listed since: 05-27-2025
Showing 64 - 84 out of 2,076 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 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 | $25,339 | $28,134 | $30,618 |
| Clean | $24,567 | $27,269 | $29,669 |
| Average | $23,280 | $25,828 | $28,086 |
| Rough | $21,607 | $23,954 | $26,029 |
The average list price of a used 2019 Toyota Highlander in Chesapeake, Virginia is $31,584. The average mileage on a used Toyota Highlander 2019 for sale in Chesapeake, Virginia is 61,596. Based on the average mileage of 61,596 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 $23,280.
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