Used Toyota Highlander for Sale in Annapolis, MD
Shop for a versatile Toyota Highlander in Sailing Capital of America
Skip to Filters
1,262 listings
- Price Drop$29,156great price$3,864 below market
- 80,046 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Bill Page Toyota (38 mi away)
Close
Located in Falls Church, VA / 38 miles away from Annapolis, MD
Certified. 2022 Toyota Highlander XLE Magnetic Gray FWD 8-Speed Automatic 3.5L V6 DOHCToyota Safety Sense 2.5+ Pre-Collision System with Pedestrian De...
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: 5TDGZRAH4NS112673
Stock: 84648A
Certified Pre-Owned: Yes
Listed since: 06-23-2025 - Price Drop$20,711great price$2,721 below market
- 104,892 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Koons Annapolis Toyota (2 mi away)
Close
Located in Annapolis, MD / 2 miles away from Annapolis, MD
**LEATHER SEATING**, **NAVIGATION**, **POWER MOONROOF**, **POWER LIFTGATE**, **BLUETOOTH**, **BACK-UP CAMERA**, **3RD ROW SEATING**, **BLIND SPOT MONI...
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: 5TDYZRFH3HS203578
Stock: KATS170112
Certified Pre-Owned: No
Listed since: 06-27-2025 - $42,000great price$4,230 below market
- 19,669 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Koons Westminster Toyota (48 mi away)
Close
Located in Westminster, MD / 48 miles away from Annapolis, MD
2024 Toyota Highlander XLE 8 Passenger **** Balance of Factory Warranty **** Apple Carplay/Android Auto, Bluetooth, Hands-Free, Sunroof, Keyless Entry...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH7RS532828
Stock: KTWP241107
Certified Pre-Owned: Yes
Listed since: 07-03-2025 - Price Drop$7,444great price$4,984 below market
- 156,568 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- Carplug of Alexandria (34 mi away)
Close
Located in Alexandria, VA / 34 miles away from Annapolis, MD
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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EH9DS200065
Stock: CP4287
Certified Pre-Owned: No - Price Drop$33,499great price$4,529 below market
- 41,693 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Hampstead Pre-Owned (47 mi away)
Close
Located in Hampstead, MD / 47 miles away from Annapolis, MD
Our 2024 Highlander is a one-owner vehicle and features all-wheel drive, back-up camera, lane keep assist, cruise control, and gray fabric seats! Tune...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH7RS529735
Stock: TGE529735
Certified Pre-Owned: No
Listed since: 06-11-2025 - Price Drop$36,981great price$3,906 below market
- 30,516 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Bill Page Toyota (38 mi away)
Close
Located in Falls Church, VA / 38 miles away from Annapolis, MD
Certified. 2024 Toyota Highlander LE Midnight Black AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpToyota Safety Sense 2.5+...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH3RS552056
Stock: P8512
Certified Pre-Owned: Yes
Listed since: 05-08-2025 - $20,800great price$3,294 below market
- 84,615 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 19 City / 25 Hwy MPG
- Len Stoler Chrysler Dodge Jeep Ram (47 mi away)
Close
Located in Westminster, MD / 47 miles away from Annapolis, MD
2016 Toyota Highlander Limited Gold 6-Speed Automatic Electronic with Overdrive FWD 3.5L V6 DOHC Dual VVT-i 24VCARFAX One-Owner. Clean CARFAX. Odomete...
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:
21 Combined MPG (19 City/25 Highway)
Listing Information:
VIN: 5TDYKRFH9GS128856
Stock: BJ1612
Certified Pre-Owned: No
Listed since: 05-29-2025 - $30,799great price$3,647 below market
- 35,136 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Hampstead Pre-Owned (47 mi away)
Close
Located in Hampstead, MD / 47 miles away from Annapolis, MD
OUr 2023 Highlander features all-wheel drive, back-up camera, lane keep assist, cruise control, and black fabric seats! Tune the radio between AM/FM t...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH1PS032855
Stock: TGE032855
Certified Pre-Owned: No
Listed since: 06-05-2025 - Price Drop$31,500great price$1,448 below market
- 20,088 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Westminster Toyota (48 mi away)
Close
Located in Westminster, MD / 48 miles away from Annapolis, MD
**** Balance of Factory Warranty ****, Bluetooth, Hands-Free, Keyless Entry, Keyless Start, Satellite Radio, AWD, Automatic temperature control.All ...
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: 5TDCZRBH2NS581709
Stock: KTWP220984
Certified Pre-Owned: No
Listed since: 06-23-2025 - Price Drop$26,000great price$3,048 below market
- 65,707 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Koons Tysons Toyota (41 mi away)
- Five Star Dealer
Close
Located in Vienna, VA / 41 miles away from Annapolis, MD
VEHICLE PROFESSIONALLY DETAILED, GOOD TIRES, GOOD BRAKES, RECENT TRADE, Highlander XLE, 4D Sport Utility, 3.5L V6, Automatic, AWD, Ooh La La Rouge Mic...
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: 5TDJZRFH4JS856797
Stock: KTTS180049
Certified Pre-Owned: Yes
Listed since: 07-03-2025 - Price Drop$37,900great price$3,172 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 (21 mi away)
Close
Located in Baltimore, MD / 21 miles away from Annapolis, MD
CARFAX One-Owner. This 2021 Magnetic Gray Toyota Highlander Platinum AWD is well equipped and includes these features and benefits:. Clean CARFAX. O...
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 - $7,995good price$2,589 below market
- 95,200 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 16 City / 22 Hwy MPG
- Ammoury Auto (38 mi away)
Close
Located in Falls Church, VA / 38 miles away from Annapolis, MD
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:
19 Combined MPG (16 City/22 Highway)
Listing Information:
VIN: JTEEP21A170223738
Stock: 2718
Certified Pre-Owned: No - New Listing$27,000great price$2,890 below market
- 69,570 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota 40 (32 mi away)
Close
Located in Edgewood, MD / 32 miles away from Annapolis, MD
CARFAX One-Owner. Clean CARFAX. 20/27 City/Highway MPG This 2022 Magnetic Gray Metallic Toyota Highlander LE AWD is well equipped and includes these 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: 5TDBZRBH5NS226612
Stock: T098902A
Certified Pre-Owned: No
Listed since: 08-01-2025 - Price Drop$37,399great price$2,990 below market
- 39,472 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Hampstead Pre-Owned (47 mi away)
Close
Located in Hampstead, MD / 47 miles away from Annapolis, MD
OUr 2023 Highlander is a one-owner vehicle and features all-wheel drive, power sunroof, heated seats, lane keep assist, dual-zone climate controls, an...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH2PS513343
Stock: TGY513343
Certified Pre-Owned: No
Listed since: 05-09-2025 - Price Drop$46,899good price$2,172 below market
- 15,074 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Hampstead Pre-Owned (47 mi away)
Close
Located in Hampstead, MD / 47 miles away from Annapolis, MD
OUr 2024 Highlander is a one-owner vehicle and features all-wheel drive, power sunroof, heated and cooled front seats, heated steering wheel, lane kee...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH1RS559765
Stock: TGE559765
Certified Pre-Owned: No
Listed since: 06-17-2025 - Price Drop$30,000great price$2,046 below market
- 30,591 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota 40 (32 mi away)
Close
Located in Edgewood, MD / 32 miles away from Annapolis, MD
**1-Owner**Apple Car Play**Back-Up Cam**3rd Row**AWD**CARFAX One-Owner. Clean CARFAX. 20/27 City/Highway MPG This 2022 Wind Chill Pearl Toyota Highl...
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: 5TDCZRBH6NS584998
Stock: A2844
Certified Pre-Owned: No
Listed since: 07-10-2025 - Price Drop$52,843fair price$86 below market
- 2,779 miles
- No accidents, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- DARCARS Toyota of Baltimore (21 mi away)
Close
Located in Baltimore, MD / 21 miles away from Annapolis, MD
2025 Toyota Highlander Platinum CARFAX One-Owner. Clean CARFAX.Highlander Platinum, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH7SS582800
Stock: 52E0146A
Certified Pre-Owned: No
Listed since: 06-24-2025 - $20,997good price$1,465 below market
- 75,997 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- Ourisman Lexus of Rockville (37 mi away)
Close
Located in Rockville, MD / 37 miles away from Annapolis, MD
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDJKRFH5FS205884
Stock: TS205884
Certified Pre-Owned: No
Listed since: 06-23-2025 - Price Drop$29,500great price$1,878 below market
- 37,012 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Toyota 40 (32 mi away)
Close
Located in Edgewood, MD / 32 miles away from Annapolis, MD
**1-Owner**Apple Car Play**Back-Up Cam**3rd Row**AWD**CARFAX One-Owner. Clean CARFAX. 20/27 City/Highway MPG This 2022 Moon Dust Toyota Highlander L...
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: 5TDCZRBHXNS216520
Stock: A2843
Certified Pre-Owned: No
Listed since: 07-10-2025 - Price Drop$20,230great price$1,451 below market
- 101,983 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 18 City / 24 Hwy MPG
- Koons Annapolis Toyota (2 mi away)
Close
Located in Annapolis, MD / 2 miles away from Annapolis, MD
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated front seats, Heated re...
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDDKRFHXGS340423
Stock: KAT250044B
Certified Pre-Owned: No
Listed since: 07-04-2025 - $20,500good price$1,429 below market
- 102,746 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 19 City / 26 Hwy MPG
- Len Stoler Chrysler Dodge Jeep Ram (47 mi away)
Close
Located in Westminster, MD / 47 miles away from Annapolis, MD
2019 Toyota Highlander LE Toasted Walnut Pearl 8-Speed Automatic Electronic with ECT-i AWD 3.5L V6Clean CARFAX.BLUETOOTH, BACK UP CAMERA, ALLOY WHEELS...
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 (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH2KS923063
Stock: BJ1607AC
Certified Pre-Owned: No
Listed since: 06-17-2025
Showing 1 - 21 out of 1,262 listings
Filters
Skip to Results