Used Toyota Sienna for Sale in Pittsfield, MA
Buy a spacious Toyota Sienna in the county seat of Berkshire County, Massachusetts
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627 listings
- $7,990fair price$381 below market
- 130,000 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 15 City / 21 Hwy MPG
- Bruce Bennett Nissan of Danbury (75 mi away)
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Located in Danbury, CT / 75 miles away from Pittsfield, MA
AWD, 2 115V Outlets, 2nd & 3rd Row Side Sunshades, 4-Corner Parking Assistance, 8-Way Power Driver Seat w/Memory, ABS brakes, Active Cruise Control, A...
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:
17 Combined MPG (15 City/21 Highway)
Listing Information:
VIN: 5TDBA22C26S060148
Stock: SW157677A
Certified Pre-Owned: No
Listed since: 02-28-2025 - Price Drop$36,041fair price$165 below market
- 49,343 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 36 City / 36 Hwy MPG
- McGee Toyota of Claremont (77 mi away)
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Located in Claremont, NH / 77 miles away from Pittsfield, MA
Recent Arrival!Alloy wheels, Apple CarPlay/Android Auto, Auto High-beam Headlights, Electronic Stability Control, Exterior Parking Camera Rear, Heated...
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:
36 Combined MPG (36 City/36 Highway)
Listing Information:
VIN: 5TDYRKEC3MS035948
Stock: 251371A
Certified Pre-Owned: No
Listed since: 07-24-2025 - $54,977fair price$213 above market
- 24,231 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 35 City / 36 Hwy MPG
- Middletown Toyota (68 mi away)
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Located in Middletown, CT / 68 miles away from Pittsfield, MA
New Price! Certified. CARFAX One-Owner. Clean CARFAX.2023 Toyota Sienna Platinum 7 Passenger AWD CVT 2.5L I4Fresh oil change, 160 point Toyota Cer...
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:
35 Combined MPG (35 City/36 Highway)
Listing Information:
VIN: 5TDESKFC3PS098042
Stock: A06435U
Certified Pre-Owned: Yes
Listed since: 06-27-2025 - New Listing$35,499good price$1,662 below market
- 32,875 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 8 Seats, 36 City / 36 Hwy MPG
- Toyota of Nashua (94 mi away)
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Located in Nashua, NH / 94 miles away from Pittsfield, MA
Recent Arrival! Toyota of Nashua is proud to present this Toyota Gold Certified... Super White 2021 Toyota Sienna LE FWD 2.5L I4 CVT CARFAX One-Owner....
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:
36 Combined MPG (36 City/36 Highway)
Listing Information:
VIN: 5TDKRKEC3MS069894
Stock: C4045
Certified Pre-Owned: Yes
Listed since: 06-13-2025 - $19,339fair price$608 below market
- 52,045 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 18 City / 25 Hwy MPG
- Romeo Toyota (62 mi away)
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Located in Glens Falls, NY / 62 miles away from Pittsfield, MA
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 (18 City/25 Highway)
Listing Information:
VIN: 5TDKK3DC0ES509597
Stock: TR2535B
Certified Pre-Owned: No
Listed since: 07-21-2025 - $53,800fair price$1,379 above market
- 19,702 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 35 City / 36 Hwy MPG
- McGovern Hyundai of Milford (92 mi away)
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Located in Milford, MA / 92 miles away from Pittsfield, MA
Recent Arrival! McGovern Hyundai Of Milford is proud to present this... Black 2023 Toyota Sienna Platinum 7 Passenger 2.5L I4 CVT AWD CARFAX One-Owner...
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:
35 Combined MPG (35 City/36 Highway)
Listing Information:
VIN: 5TDESKFCXPS097003
Stock: HN2855A
Certified Pre-Owned: No
Listed since: 05-18-2025 - $36,899good price$1,811 below market
- 52,100 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 18 City / 24 Hwy MPG
- Toyota of Nashua (94 mi away)
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Located in Nashua, NH / 94 miles away from Pittsfield, MA
Recent Arrival! Toyota of Nashua is proud to present this Toyota Gold Certified... Blizzard Pearl White 2020 Toyota Sienna Limited AWD 3.5L V6 SMPI DO...
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: 5TDDZ3DC6LS228101
Stock: C4089
Certified Pre-Owned: Yes
Listed since: 07-08-2025 - $48,299fair price$62 above market
- 28,664 miles
- No accidents, 1 owner, personal use
- 7 Seats, 35 City / 36 Hwy MPG
- Toyota of Nashua (94 mi away)
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Located in Nashua, NH / 94 miles away from Pittsfield, MA
Recent Arrival! Toyota of Nashua is proud to present this Toyota Gold Certified... Celestial Silver Metallic 2023 Toyota Sienna XLE AWD 2.5L I4 CVT CA...
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:
35 Combined MPG (35 City/36 Highway)
Listing Information:
VIN: 5TDYSKFCXPS077380
Stock: N24520C
Certified Pre-Owned: Yes
Listed since: 06-10-2025 - New Listing$11,995good price$2,433 below market
- 100,670 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 18 City / 25 Hwy MPG
- United Auto Wholesale (52 mi away)
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Located in East Windsor, CT / 52 miles away from Pittsfield, MA
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 (18 City/25 Highway)
Listing Information:
VIN: 5TDKK3DC2CS187106
Stock: C25021
Certified Pre-Owned: No - $24,998fair price$1,495 above market
- 81,977 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Faith's Toyota (62 mi away)
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Located in Westminster, VT / 62 miles away from Pittsfield, MA
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: 5TDJZ3DC2KS211927
Stock: T15682A
Certified Pre-Owned: No
Listed since: 06-11-2025 - $50,645fair price$132 above market
- 41,779 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 35 City / 36 Hwy MPG
- McGee Toyota of Claremont (77 mi away)
Close
Located in Claremont, NH / 77 miles away from Pittsfield, MA
Recent Arrival!AWD, 1500W Inverter Output, Alloy wheels, Apple CarPlay/Android Auto, Auto High-beam Headlights, Electronic Stability Control, Front du...
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:
35 Combined MPG (35 City/36 Highway)
Listing Information:
VIN: 5TDESKFC5PS096258
Stock: 251373A
Certified Pre-Owned: No
Listed since: 07-25-2025 - $23,500fair price$285 below market
- 100,928 miles
- 2 accidents, 1 owner, personal use only
- 8 Seats, 19 City / 27 Hwy MPG
- Toyota of Colchester (77 mi away)
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Located in Colchester, CT / 77 miles away from Pittsfield, MA
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 (19 City/27 Highway)
Listing Information:
VIN: 5TDYZ3DC6JS937044
Stock: 20238
Certified Pre-Owned: No
Listed since: 04-16-2025 - New Listing$40,999fair price$527 above market
- 55,469 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 36 City / 36 Hwy MPG
- Enterprise Car Sales East Hartford (57 mi away)
- Home delivery*
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Located in East Hartford, CT / 57 miles away from Pittsfield, MA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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:
36 Combined MPG (36 City/36 Highway)
Listing Information:
VIN: 5TDYRKEC9PS169058
Stock: 7WLL4H
Certified Pre-Owned: No
Listed since: 07-16-2025 - New Listing
- 10 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 35 City / 36 Hwy MPG
- McGee Toyota of Claremont (77 mi away)
Close
Located in Claremont, NH / 77 miles away from Pittsfield, MA
Good to go from day 1!AWD, 1500W Inverter Output, Alloy wheels, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, Front dual zone A/C, Heated ...
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:
35 Combined MPG (35 City/36 Highway)
Listing Information:
VIN: 5TDJSKFC8SS190707
Stock: 251012
Certified Pre-Owned: Yes
Listed since: 06-09-2025 - 181,645 miles
- No accidents, 3 owners, corporate fleet vehicle
- 7 Seats, 18 City / 24 Hwy MPG
- Westboro Toyota (83 mi away)
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Located in Westborough, MA / 83 miles away from Pittsfield, MA
AWD, 18" x 7" 10-Spoke Machine Finish Alloy Wheels, ABS brakes, Alloy wheels, Bumpers: body-color, Compass, Electronic Stability Control, Front dual z...
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDDZ3DC6HS164083
Stock: T77659A
Certified Pre-Owned: No
Listed since: 07-16-2025- $24,995good price$3,115 below market
- 79,079 miles
- 2 accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 19 City / 27 Hwy MPG
- Prestige Auto Cars (61 mi away)
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Located in New Britain, CT / 61 miles away from Pittsfield, MA
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:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 5TDYZ3DCXKS995417
Stock: 995417
Certified Pre-Owned: No - 222,499 miles
- No accidents, 2 owners, personal use
- 7 Seats, 16 City / 23 Hwy MPG
- Driveway (68 mi away)
- Home delivery*
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Located in Wappingers Falls, NY / 68 miles away from Pittsfield, MA
CarFax No Accidents Reported,Rare Find,3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Entertainment System,Heated Seats,Keyless...
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/23 Highway)
Listing Information:
VIN: 5TDDK3DC9GS129847
Stock: 620327A
Certified Pre-Owned: No- New Listing$13,873fair price$993 below market
- 110,057 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 18 City / 25 Hwy MPG
- Smart Buy Auto Sales (69 mi away)
Close
Located in Meriden, CT / 69 miles away from Pittsfield, MA
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 (18 City/25 Highway)
Listing Information:
VIN: 5TDKK3DC0ES430009
Stock: 4639
Certified Pre-Owned: No - 25,409 miles
- No accidents, 5 owners, personal use only
- 8 Seats, 19 City / 27 Hwy MPG
- CarMax East Haven (83 mi away)
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Located in East Haven, CT / 83 miles away from Pittsfield, MA
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:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 5TDXZ3DC8HS847898
Stock: 26665571
Certified Pre-Owned: No- $11,950good price$1,101 below market
- 137,105 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 18 City / 25 Hwy MPG
- All County Auto Sales (89 mi away)
Close
Located in Bridgeport, CT / 89 miles away from Pittsfield, MA
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:
21 Combined MPG (18 City/25 Highway)
Listing Information:
VIN: 5TDZK3DC4FS664086
Stock: 1009
Certified Pre-Owned: No - $13,995fair price$103 below market
- 134,900 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 18 City / 25 Hwy MPG
- Y & H Auto Planet (26 mi away)
Close
Located in Rensselaer, NY / 26 miles away from Pittsfield, MA
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 (18 City/25 Highway)
Listing Information:
VIN: 5TDYK3DC3DS373636
Stock: 373636
Certified Pre-Owned: No
Showing 22 - 42 out of 627 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.