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2,118 listings
- $25,786great price$5,279 below market
- 73,546 miles
- No accidents, 3 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Royal Auto Club (169 mi away)
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Located in Sterling, VA / 169 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH2MS072476
Stock: SAI2840
Certified Pre-Owned: No - $24,999great price$3,057 below market
- 110,221 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 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: 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: 5TDHZRBH8MS116355
Stock: 116355
Certified Pre-Owned: No - Price Drop$29,500great price$2,961 below market
- 80,764 miles
- No accidents, 1 owner, personal use only
- 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! 2021 Toyota Highlander XLE 2021 Toyota Highlander XLE in Blueprint, Please call 410-822-8000 with any equipment or availability questi...
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: 5TDHZRBH9MS144178
Stock: KETP210131
Certified Pre-Owned: Yes
Listed since: 07-16-2025 - Price Drop$38,500great price$2,662 below market
- 26,746 miles
- No accidents, 1 owner, personal use
- 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. Recent Arrival! This 2021 Magnetic Gray Toyota Highlander Platinum AWD is well equipped and includes these features and benefits:....
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: 5TDFZRBH3MS123995
Stock: B4708
Certified Pre-Owned: No
Listed since: 07-12-2025 - Price Drop$34,709great price$2,269 below market
- 65,122 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 21 City / 29 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**, **NAVIGATION**, **POWER MOONROOF**, **POWER LIFTGATE**, **BLUETOOTH**, **BACK-UP CAMERA**, **3RD ROW SEATIN...
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: 5TDFZRAHXMS050979
Stock: KATP230100B
Certified Pre-Owned: No
Listed since: 06-20-2025 - Price Drop$25,000great price$2,658 below market
- 67,648 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
This 2021 Black Toyota Highlander LE AWD is well equipped and includes these features and benefits:.20/27 City/Highway MPG Bluetooth, APPLE CARPLAY/AN...
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: 5141EA
Certified Pre-Owned: No
Listed since: 05-30-2025 - Price Drop$30,474great price$2,166 below market
- 75,268 miles
- 1 accident, 1 owner, personal use only
- 8 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
++1-OWNER++ LIMITED PACKAGE++AWD++ 2021 Toyota Highlander Limited 3.5L V6 DOHC 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: 5TDDZRBH5MS526657
Stock: T18858A
Certified Pre-Owned: No
Listed since: 05-30-2025 - $30,777good price$1,930 below market
- 32,532 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Lease Return Center (140 mi away)
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Located in Triangle, VA / 140 miles away from Chesapeake, VA
--GORGEOUS PEARL WHITE ON BLACK LEATHER--SUPER CLEAN AND CARFAX CERTIFIED!!!--ONLY 32K MILES!!!--FULLY LOADED WITH EVERY OPTIONS!!!--LOOKS AND RUNS AM...
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: 5TDGZRAH4MS520816
Stock: 20816
Certified Pre-Owned: No - New Listing$29,000fair price$568 below market
- 79,101 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 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
2021 Toyota Highlander XLE ABS brakes, Automatic temperature control, Heated front seats, Power driver seat, Power Liftgate. Arlington Toyota is a One...
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: 5TDGZRBH3MS530803
Stock: 10860
Certified Pre-Owned: No
Listed since: 06-11-2025 - Price Drop$34,500good price$2,010 below market
- 20,443 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Auto Giants Mitsubishi (157 mi away)
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Located in Manassas, VA / 157 miles away from Chesapeake, VA
Summer is Heating Up!2021 Toyota Highlander XLE Ruby Flare PearlKEY FEATURES INCLUDE:, AWD, APPLE CARPLAY, ANDROID AUTO, TOUCHSCREEN/ INFOTAINMENT, LE...
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: 5TDGZRBH8MS557849
Stock: U2746
Certified Pre-Owned: No
Listed since: 07-03-2025 - Price Drop$38,384fair price$144 above market
- 49,665 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Leith Toyota (142 mi away)
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Located in Raleigh, NC / 142 miles away from Chesapeake, VA
Clean CARFAX. CARFAX One-Owner. Ruby Flare Pearl 2021 Toyota Highlander Platinum AWD 8-Speed Automatic 3.5L V6 DOHC Clean Carfax 1 Owner/No Accident V...
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: 5TDFZRBH7MS120985
Stock: T120985AA
Certified Pre-Owned: No
Listed since: 06-14-2025 - $33,500fair price$721 below market
- 42,131 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Len Stoler Lexus (190 mi away)
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Located in Owings Mills, MD / 190 miles away from Chesapeake, VA
CARFAX One-Owner.Magnetic Gray Metallic 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHCAWD.Odometer is 13407 miles below market average!...
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: 5TDGZRBH1MS138936
Stock: BL1501
Certified Pre-Owned: No
Listed since: 06-02-2025 - Price Drop$33,500good price$1,604 below market
- 42,903 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota 40 (187 mi away)
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Located in Edgewood, MD / 187 miles away from Chesapeake, VA
**1-Owner**Apple Car Play**Back-Up Cam**3rd Row**AWD**CARFAX One-Owner. Clean CARFAX. 20/27 City/Highway MPG This 2021 Midnight Black Metallic Toyot...
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: 5TDHZRBH8MS540702
Stock: A2841
Certified Pre-Owned: No
Listed since: 07-10-2025 - Price Drop$28,051good price$994 below market
- 93,581 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Capital Subaru of Greenville (104 mi away)
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Located in Winterville, NC / 104 miles away from Chesapeake, VA
Capital Subaru of Greenville is pleased to offer this gorgeous 2021 Toyota Highlander Celestial Silver Metallic XLE with the following features:Leat...
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: 5TDGZRBH1MS087339
Stock: SAT4160A
Certified Pre-Owned: No
Listed since: 05-20-2025 - Price Drop$35,998good price$998 below market
- 40,361 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Laurel (169 mi away)
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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: 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH2MS158988
Stock: 27191974
Certified Pre-Owned: No - $32,995fair price$144 below 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$34,000good price$1,830 below market
- 25,677 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Hanna Imports (148 mi away)
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Located in Raleigh, NC / 148 miles away from Chesapeake, VA
CARFAX One-Owner. Leather Seats, Bluetooth, *Multi Point Inspection*, Highlander XLE, AWD, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, P...
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: 5TDGZRBH1MS094422
Stock: 3021587
Certified Pre-Owned: No
Listed since: 04-27-2025 - $33,551fair price$145 below market
- 51,867 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Beyer Volvo Cars Dulles (171 mi away)
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Located in Sterling, VA / 171 miles away from Chesapeake, VA
AWD.CARFAX One-Owner. Clean CARFAX.Odometer is 5143 miles below market average!No Haggle Easy Pricing.Awards:* ALG Residual Value Awards, Residual Val...
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: 5TDHZRBH0MS124191
Stock: T17641K
Certified Pre-Owned: No
Listed since: 07-07-2025 - $34,911good price$1,587 below market
- 44,155 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Heritage Toyota Catonsville (179 mi away)
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Located in Catonsville, MD / 179 miles away from Chesapeake, VA
JUST ARRIVED. PENDING INSPECTION. *APPLE CARPLAY/ANDROID AUTO*, *HANDS FREE BLUETOOTH*, *CARFAX ONE OWNER VEHICLE*, *POWER SUNROOF*, *BLIND SPOT SENSO...
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: 5TDDZRBH7MS543072
Stock: 3U543072
Certified Pre-Owned: No
Listed since: 07-15-2025 - New Listing$33,998good price$1,273 below market
- 48,941 miles
- 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 Unavailable.
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDYZRAH6MS517159
Stock: 26953050
Certified Pre-Owned: No - Price Drop$33,550fair price$239 above market
- 51,546 miles
- No accidents, 2 owners, rental 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,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
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: 5TDGZRBH2MS525558
Stock: MS525558P
Certified Pre-Owned: No
Showing 1 - 21 out of 2,118 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 XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $28,989 | $31,142 | $33,301 |
| Clean | $28,372 | $30,463 | $32,559 |
| Average | $27,343 | $29,332 | $31,322 |
| Rough | $26,006 | $27,862 | $29,713 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $32,175. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 57,170. Based on the average mileage of 57,170 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 $27,343.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.