Used Toyota Highlander for Sale in Middletown, CT
Shop for a versatile Toyota Highlander in the county seat for Middlesex County, Connecticut
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1,260 listings
- $14,995great price$3,026 below market
- 100,300 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- A Better Way Wholesale Autos (19 mi away)
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Located in Naugatuck, CT / 19 miles away from Middletown, CT
- Experience luxury with a sophisticated black exterior and plush gray leather interior. - Powered by a robust 3.5L V6 engine delivering 270hp with a...
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: 5TDJKRFH4FS161358
Stock: 161358N
Certified Pre-Owned: No - $40,833good price$3,199 below market
- 5,952 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Ingersoll Auto of Danbury (41 mi away)
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Located in Danbury, CT / 41 miles away from Middletown, CT
Priced below KBB Fair Purchase Price! Odometer is 10132 miles below market average! Clean CARFAX. 18' Painted Alloy Wheels, 3rd row seats: split-bench...
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: 5TDKDRBH3RS532762
Stock: A532762
Certified Pre-Owned: No
Listed since: 06-20-2025 - $13,995good price$2,703 below market
- 99,437 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (19 mi away)
Close
Located in Naugatuck, CT / 19 miles away from Middletown, CT
- Experience the perfect blend of power and efficiency with a robust 3.5L V6 engine delivering 270hp. - Luxurious leather interior ensures comfort an...
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: 5TDDK3EH0CS160389
Stock: 160389N
Certified Pre-Owned: No - $11,995good price$1,631 below market
- 118,333 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (19 mi away)
Close
Located in Naugatuck, CT / 19 miles away from Middletown, CT
- **Proven Reliability:** Award-winning dependability and quality from J.D. Power and Kelley Blue Book. - **Powerful Performance:** Robust 3.5L V6 en...
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 (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH1CS101004
Stock: 101004N
Certified Pre-Owned: No - $10,495good price$1,459 below market
- 133,554 miles
- No accidents, 3 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (19 mi away)
Close
Located in Naugatuck, CT / 19 miles away from Middletown, CT
- Experience the perfect blend of power and efficiency with a robust 3.5L V6 engine delivering 270 horsepower. - Enjoy peace of mind with top accolad...
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 (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH9CS100411
Stock: 100411N
Certified Pre-Owned: No - Price Drop$10,995good price$975 below market
- 113,382 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 17 City / 22 Hwy MPG
- A Better Way Wholesale Autos (19 mi away)
Close
Located in Naugatuck, CT / 19 miles away from Middletown, CT
- Reliable and powerful 3.5L V6 engine with 270 horsepower - Spacious interior with second-row rear vents and privacy glass - Award-winning family 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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDBK3EH8BS062068
Stock: 62068N
Certified Pre-Owned: No - $6,450fair price$1,081 below market
- 144,525 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 16 City / 22 Hwy MPG
- Choice Motor Car (13 mi away)
Close
Located in Plainville, CT / 13 miles away from Middletown, CT
Nice, clean, loaded up Highlander in great condition inside and out. Leather seats, power sliding sunroof, 4wd, power windows locks and seat, nice ne...
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 (16 City/22 Highway)
Listing Information:
VIN: JTEEP21A550080550
Stock: 080550
Certified Pre-Owned: No
Listed since: 09-10-2024 - Price Drop$37,995fair price$216 below market
- 35,277 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- McGee Toyota of Putnam (48 mi away)
Close
Located in Putnam, CT / 48 miles away from Middletown, CT
McGee Toyota of Putnam is proud to present you with this 2023 Toyota Highlander XLE! ---------- ONE (1) OWNER TRADE-IN, CLEAN CARFAX, AWD, 2.4L I...
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: 5TDKDRBH6PS042250
Stock: 25628TA
Certified Pre-Owned: No
Listed since: 06-13-2025 - New Listing$15,995good price$1,057 below market
- 131,332 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 18 City / 24 Hwy MPG
- A Better Way Wholesale Autos (19 mi away)
Close
Located in Naugatuck, CT / 19 miles away from Middletown, CT
- **Proven Reliability**: Award-winning 2016 Toyota Highlander XLE with a 3.5L V6 engine, recognized by Edmunds, J.D. Power, and Kelley Blue Book for ...
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: 5TDJKRFH0GS240351
Stock: 240351N
Certified Pre-Owned: No - Price Drop$41,851good price$1,482 below market
- 13,048 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Ingersoll Auto of Danbury (41 mi away)
Close
Located in Danbury, CT / 41 miles away from Middletown, CT
Priced below KBB Fair Purchase Price! Odometer is 11272 miles below market average! CARFAX One-Owner. Clean CARFAX. Back-Up Camera, 18' Painted Alloy ...
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: 5TDKDRBH8RS568057
Stock: A568057
Certified Pre-Owned: No
Listed since: 07-07-2025 - $21,995good price$1,344 below market
- 97,051 miles
- No accidents, 4 owners, corporate fleet vehicle
- 8 Seats, 20 City / 26 Hwy MPG
- A Better Way Wholesale Autos (19 mi away)
Close
Located in Naugatuck, CT / 19 miles away from Middletown, CT
- **Low Mileage & Powerful Performance**: With only 97,051 miles, this 2018 Toyota Highlander SE is equipped with a robust 3.5L V6 engine delivering 2...
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: 5TDJZRFH1JS822414
Stock: 822414N
Certified Pre-Owned: No - $5,900great price$1,723 below market
- 192,000 miles
- No accidents, 2 owners, personal use
- 7 Seats, 17 City / 23 Hwy MPG
- Brodster's Roadsters (43 mi away)
Close
Located in New Fairfield, CT / 43 miles away from Middletown, CT
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 (17 City/23 Highway)
Listing Information:
VIN: 5TDJK3EH0AS026952
Stock: 026952
Certified Pre-Owned: No - $25,199great price$3,693 below market
- 74,758 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Prestige Auto Cars (8 mi away)
- Home delivery*
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Located in New Britain, CT / 8 miles away from Middletown, CT
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: 5TDCZRBH5MS128926
Stock: 128926
Certified Pre-Owned: No - Price Drop$21,353good price$846 below market
- 98,403 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Bruce Bennett Nissan of Danbury (44 mi away)
Close
Located in Danbury, CT / 44 miles away from Middletown, CT
BLUETOOTH/HANDS FREE/CELL PHONE, BACK UP CAMERA, FORWARD COLLISION WARNING, BLIND SPOT WARNING ALERT, REAR CROSS TRAFFIC ALERT, CLEAN CARFAX/NO ACCIDE...
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: 5TDJZRFH8JS874302
Stock: SC115061A
Certified Pre-Owned: No
Listed since: 06-02-2025 - New Listing$18,995good price$1,316 below market
- 126,409 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Toyota of Colchester (17 mi away)
Close
Located in Colchester, CT / 17 miles away from Middletown, CT
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: 5TDJZRFH9JS863793
Stock: 20256A
Certified Pre-Owned: No
Listed since: 07-19-2025 - Price Drop$34,995fair price$297 above market
- 41,837 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Greentree Toyota (41 mi away)
Close
Located in Danbury, CT / 41 miles away from Middletown, CT
Certified. 2021 Toyota Highlander XLE AWDAWD.Highlander AWD XLE AWD Silver 3.5L V6 DOHC 8-Speed Automatic 4D Sport Utility Odometer is 12747 miles b...
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: 5TDGZRBH4MS069241
Stock: U22549
Certified Pre-Owned: Yes
Listed since: 06-12-2025 - Price Drop$24,206fair price$237 below market
- 88,640 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Lia Toyota of Wilbraham (43 mi away)
Close
Located in Wilbraham, MA / 43 miles away from Middletown, CT
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: 5TDJZRFH5JS559067
Stock: JS559067T
Certified Pre-Owned: No
Listed since: 06-30-2025 - $39,998good price$2,142 below market
- 40,740 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- McGee Toyota of Putnam (48 mi away)
Close
Located in Putnam, CT / 48 miles away from Middletown, CT
McGee Toyota of Putnam is proud to present you with this 2023 Toyota Highlander Platinum! ---------- ONE OWNER, CLEAN CARFAX, AWD, 2.4 I-4 TURBO...
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: 5TDKDRBH5PS031403
Stock: 25357A
Certified Pre-Owned: No
Listed since: 05-17-2025 - $40,499fair price$121 below market
- 32,107 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Lia Toyota of Wilbraham (43 mi away)
Close
Located in Wilbraham, MA / 43 miles away from Middletown, CT
Wind Chill Pearl 2022 Toyota Highlander Limited 3.5L V6 DOHC 8-Speed Automatic AWDOne Owner *, Clean Car-Fax *, Service Records Available *, Back Up 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: 5TDDZRBH1NS185839
Stock: NS185839T
Certified Pre-Owned: No
Listed since: 07-03-2025 - $42,990fair price$859 below market
- 21,508 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Middletown Toyota (2 mi away)
Close
Located in Middletown, CT / 2 miles away from Middletown, CT
Recent Arrival! Certified. CARFAX One-Owner. Clean CARFAX.2023 Toyota Highlander XSE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SU...
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: 5TDKDRBH6PS514155
Stock: BL07459U
Certified Pre-Owned: Yes
Listed since: 07-16-2025 - New Listing$36,499fair price$334 below market
- 36,699 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lia Toyota of Wilbraham (43 mi away)
Close
Located in Wilbraham, MA / 43 miles away from Middletown, CT
Recent Arrival! Magnetic Gray Metallic 2022 Toyota Highlander XLE 3.5L V6 DOHC 8-Speed Automatic AWDOne Owner *, Clean Car-Fax *, Service Records Avai...
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: 5TDGZRBH1NS226158
Stock: NS226158L
Certified Pre-Owned: No
Listed since: 07-21-2025
Showing 1 - 21 out of 1,260 listings
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.