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2,071 listings
- New Listing$33,998fair price$745 below market
- 48,941 miles
- 1 accident, 2 owners, rental vehicle
- 7 Seats, 21 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: 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: 5TDYZRAH6MS517159
Stock: 26953050
Certified Pre-Owned: No - $29,500fair price$645 below market
- 90,576 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Bumble Auto (173 mi away)
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Located in Elkridge, MD / 173 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 - $32,995fair price$136 above market
- 78,352 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Global Auto Outlet (150 mi away)
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Located in Temple Hills, MD / 150 miles away from Chesapeake, VA
Estimated monthly payment and estimated total purchase price include the Maryland processing fee of $800 (not required by law). Taxes and additional f...
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: 5TDLZRBH8MS102885
Stock: 102885
Certified Pre-Owned: No
Listed since: 05-29-2025 - Price Drop$36,990fair price$802 above market
- 67,409 miles
- No accidents, 1 owner, 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: 5TDFZRBH9MS104416
Stock: 2003888170
Certified Pre-Owned: No
Listed since: 07-10-2025 - Price Drop$36,500fair price$345 above market
- 44,457 miles
- No accidents, 2 owners, personal use
- 7 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! 2021 Toyota Highlander Limited 2021 Toyota Highlander Limited in Opulent Amber, Please call 410-822-8000 with any equipment or availab...
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: 5TDDZRBH7MS121609
Stock: KETP210123
Certified Pre-Owned: No
Listed since: 07-11-2025 - $36,950fair price$449 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: 05-22-2025 - $31,998fair price$116 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
2021 Toyota Highlander XSE.. AWD.. 3.5L V6.. Midnight Black with Black Leather.. Apple Car Play Navigation.. Power Sunroof.. Heated Seats.. Rear Capta...
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 - 4,355 miles
- Frame damage reported, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Kargar Motors (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
BUYING A CAR HAS NEVER BEEN THIS EASY.We specialize in 100% GUARANTEED APPROVAL. BAD CREDIT, NO CREDIT, BANKRUPTCY, REPO, FORECLOSURE...NO PROBLEM. NO...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDFZRAH3MS067798
Stock: KMM13684
Certified Pre-Owned: No- $33,495fair price$203 below market
- 43,984 miles
- 2 accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Auction Direct USA (151 mi away)
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Located in Raleigh, NC / 151 miles away from Chesapeake, VA
The 2021 Toyota Highlander XLE is the family SUV that doesnt forget to flex. With a powerful V6, comfy tech-packed cabin, and room for the whole crew,...
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: 5TDGZRBH8MS548634
Stock: AD01052
Certified Pre-Owned: No
Listed since: 05-09-2025 - Price Drop$31,995fair price$341 below market
- 86,158 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Regnum Auto Motors (157 mi away)
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Located in Manassas, VA / 157 miles away from Chesapeake, VA
*2021 Toyota Highlander XSE for Sale in Manassas, VA | AWD Luxury SUV with Advanced Safety and Premium Features*The 2021 Toyota Highlander XSE is a st...
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: 5TDJZRBH2MS077182
Stock: 077182
Certified Pre-Owned: No
Listed since: 07-11-2025 - New Listing$28,997fair price$666 below market
- 41,285 miles
- 1 accident, 2 owners, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- Ourisman Lexus of Rockville (172 mi away)
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Located in Rockville, MD / 172 miles away from Chesapeake, VA
18 ALLOY WHEELS, BLUE TOOTH, BACK UP CAMERA, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, AM/FM radio: SiriusXM, Auto High-beam Head...
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: 5TDCZRAH1MS071979
Stock: TS071979
Certified Pre-Owned: No
Listed since: 07-24-2025 - $32,795fair price$124 below market
- 46,362 miles
- 2 accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Koons of Woodbridge (142 mi away)
Close
Located in Woodbridge, VA / 142 miles away from Chesapeake, VA
Visit Koons Automotive of Woodbridge online at www.koonsofwoodbridge.com to see more pictures of this vehicle or call us at 571-285-3277 today to sch...
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: 5TDGZRBH7MS543814
Stock: 35254
Certified Pre-Owned: No - $32,000fair price$168 below market
- 84,605 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Beyer Kia Falls Church (158 mi away)
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Located in Falls Church, VA / 158 miles away from Chesapeake, VA
AWD.Red 2021 Toyota Highlander LimitedAWD 8-Speed Automatic 3.5L V6 DOHC Recent Arrival! 20/27 City/Highway MPG
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: 5TDDZRBH1MS526607
Stock: E10748VK
Certified Pre-Owned: No
Listed since: 05-29-2025 - $35,998fair price$452 above market
- 19,296 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Jacksonville NC (149 mi away)
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Located in Jacksonville, NC / 149 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 - New Listing$36,900fair price$88 above market
- 48,201 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Hall Toyota Elizabeth City (31 mi away)
- Home delivery*
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Located in Elizabeth City, NC / 31 miles away from Chesapeake, VA
JUST ARRIVED. PENDING INSPECTION. We are currently offering Vehicle Purchase Home Delivery by appointment. Please contact for details., AWD. Blizzard ...
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: 5TDDZRBH9MS078746
Stock: 22255518A
Certified Pre-Owned: No
Listed since: 07-21-2025 - New Listing$35,738fair price$249 above market
- 27,733 miles
- No accidents, 2 owners, 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! 2021 Toyota Highlander XLE Moon Dust AWD AutomaticSunroof/Moonroof, Heated Seats, Blind Spot Monitor, Backup Camera, Bluetooth, USB ...
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: 5TDGZRBH0MS064554
Stock: B8899
Certified Pre-Owned: No
Listed since: 07-19-2025 - Price Drop$33,918fair price$441 above market
- 68,920 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Silver Spring (166 mi away)
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Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
2021 Toyota Highlander Limited Clean CARFAX.Celestial Silver AWD. AWD 3.5L V6 DOHC 8-Speed Automatic 20/27 City/Highway MPG
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: 5TDDZRBH4MS538833
Stock: P1A1435
Certified Pre-Owned: No
Listed since: 07-08-2025 - New Listing$36,998fair price$333 above market
- 25,683 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Laurel (169 mi away)
Close
Located in Laurel, MD / 169 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: 5TDGZRBH9MS559223
Stock: 27204095
Certified Pre-Owned: No - New Listing$34,998fair price$19 above market
- 47,970 miles
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Brandywine (139 mi away)
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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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDLZRBH9MS153330
Stock: 27472728
Certified Pre-Owned: No - 63,689 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
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Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keepi...
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: 5TDGZRBHXMS091910
Stock: MS091910VA
Certified Pre-Owned: No- New Listing
- 105,087 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- West Broad Hyundai (96 mi away)
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Located in Richmond, VA / 96 miles away from Chesapeake, VA
20/27 City/Highway MPG Awards: * ALG Residual Value Awards, Residual Value Awards See the rest of our inventory at: WESTBROADHYUNDAI.COM.
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: 5TDGZRBH8MS524382
Stock: 257432A
Certified Pre-Owned: No
Listed since: 05-31-2025
Showing 22 - 42 out of 2,071 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 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $30,325 | $32,529 | $34,739 |
| Clean | $29,680 | $31,820 | $33,964 |
| Average | $28,604 | $30,639 | $32,674 |
| Rough | $27,205 | $29,103 | $30,995 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $33,959. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 56,055. Based on the average mileage of 56,055 for used 2021 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 2021 in Chesapeake, Virginia to be $28,604.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.