386 Cheshire Rd

$399,900
Price
3
Beds
2,191 Sq. Ft.
$183 / Sq. Ft.
2,191
Sq. Ft.
$183
per Sq. Ft.

Description

Step into this beautifully renovated home, where natural sunlight fills spacious, oversized rooms, creating a warm and inviting atmosphere. Every detail has been thoughtfully updated, showcasing a fresh, modern aesthetic complemented by brand-new appliances. The expansive primary bedroom features two closets, with one large enough to serve as a nursery or home office, complete with two windows for abundant light. Perfectly positioned in a prime location—just minutes from Jiminy Peak Mountain Resort,...Step into this beautifully renovated home, where natural sunlight fills spacious, oversized rooms, creating a warm and inviting atmosphere. Every detail has been thoughtfully updated, showcasing a fresh, modern aesthetic complemented by brand-new appliances. The expansive primary bedroom features two closets, with one large enough to serve as a nursery or home office, complete with two windows for abundant light. Perfectly positioned in a prime location—just minutes from Jiminy Peak Mountain Resort, tranquil lakes, and convenient shopping—this home seamlessly blends comfort, style, and accessibility.
  1. Listed by Debra Goddeau • ASHMERE REALTY, INC. • 413-655-0003

Property Details for 386 Cheshire Road

Architectural Style
Colonial
Parking Spaces Type
Off Street
Zoning Description
Residential
LISTING UPDATED: 11/16/2025 11:34 AM

Property Details for 386 Cheshire Road

StatusActive
MLS #248155
Days on Market52
Taxes$3,780 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1932
Lot Size0.53 AC / 23,087 SF
CountyBerkshire County

Location

Listing Courtesy of ASHMERE REALTY, INC., Debra Goddeau
Add your commute

Building Information for 386 Cheshire Road

Stories-Year Built1932Building Size-Lot Size0.53 AC / 23,087 SF

Payment Calculator

$2,291 per month

30 year fixed, 6.28% Interest

Principal and Interest

$1,976

Property Taxes

$315

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 386 Cheshire Road

Summary
Location and General Information
  • Directions: Rt. 8 North, Cheshire Road. Look for sign.
  • MLS Area Major: Middle Registry
  • Latitude: 42.48
  • Longitude: -73.20
  • MLS Area Minor: Middle Registry
Taxes and HOA
  • Tax Book Number: 2995
  • Parcel Number: PITT M:L16 B:0002 L:003
  • Association Fee: $.00
  • Tax Amount: $3,780.00
  • Tax Year: 2025
  • Book: 2995
  • Page: 238
School Information
  • Middle Or Junior School: John T Reid
  • High School: Taconic
  • Elementary School: Allendale
  • Elementry School: Allendale
  • Middle School: John T Reid
Parking
  • Other Parking: Off Street
  • Attached Garage: No
  • Garage None: Yes
Virtual Tour
  • Virtual Tours Count: 0
Property
Lot Information
  • Lot Size Area: 0.53
  • Lot Size Units: Acres
  • Lot Size Acres: 0.53
  • Lot Size Dimensions: 22,895 sqft
  • Lot Size Square Feet: 23087.0
  • Square Feet Source: Assessor
  • Living Area: 2191.0
  • Building Area Total: 2191.0
  • Property Type: Residential
  • Restrict Covenants Unknown: Yes
Property and Assessments
  • Floor Plans Count: 0
  • Total Bathrooms Source: MLS
  • Photos Count: 45
  • Videos Count: 0
  • Documents Count: 2
  • Property Type: Residential
  • Betterment: No
  • Easement Unknown: Yes
  • Survey Unknown: Yes
  • Year Built: 1932
  • Year Built Source: Assessor
  • Flood Hazard Area No: Yes
  • Title V Not Applicable: Yes
Utilities
  • Sewer: Public
  • Water Yes: Yes
  • Water Access Public: Yes
  • Sewer Public: Yes
  • Electric Type 200 Amp: Yes
  • Internet Service Cable Available: Yes
Interior and Exterior Features
Exterior Features
  • Exterior Features: Trash Public, Curbside Recycling, Bus-Public, Fenced-Partially, Outbuilding, Patio
  • Exterior Amenities Bus Public: Yes
  • Exterior Amenities FencedPartially: Yes
  • Exterior Amenities Outbuilding: Yes
  • Exterior Amenities Patio: Yes
  • Exterior Amenities Trash Public: Yes
  • Exterior Amenities Curbside Recycling: Yes
  • Exterior Siding Wood: Yes
  • Right of Way Unknown: Yes
  • Post Beam Wood Frame: Yes
  • Style Colonial: Yes
Interior Features
  • Baths Total: 2.00
  • Baths Full: 2
  • Total Bathrooms: 2
  • Bathrooms Total Decimal: 2.00
  • Bathrooms Total Notational: 2.00
  • Total Rooms: 6.00
  • Heating: Nat Gas, Boiler, Hot Water
  • Kitchen Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer
  • Heating: Yes
  • Underground Oil Tank No: Yes
  • Building Information Exterior Color: Gray
  • Interior Features: Cable Available, Walk-In Closet(s)
  • Interior Amenities WalkIn Closet: Yes
  • Basement Concrete Floor: Yes
  • Basement Interior Access: Yes
  • Basement Unfinished: Yes
  • Basement Walkout: Yes
  • Fuel Nat Gas: Yes
  • Hot Water Nat Gas: Yes
  • Insulation Fiberglass: Yes
  • Appliances Included Dishwasher: Yes
  • Appliances Included Dryer: Yes
  • Appliances Included Refrigerator: Yes
  • Appliances Included Washer: Yes
  • Floor Laminate: Yes
  • Heat/Cool/Vent Hot Water: Yes
  • Heat/Cool/Vent Boiler: Yes
  • Lead Paint Unk: Yes
Room Information
Room Details
  • Rooms Total: 6
  • Room Type: Kitchen, Dining Room, Living Room, Mud Room, Full Bathroom, Bedroom 1, Bedroom 2, Bedroom 3
Room 1
  • Room Type: Kitchen
  • Room Level: First
Room 2
  • Room Type: Dining Room
  • Room Level: First
Room 3
  • Room Type: Living Room
  • Room Level: First
Room 4
  • Room Type: Mud Room
  • Room Level: First
Room 5
  • Room Type: Full Bathroom
  • Room Level: First
Room 6
  • Room Type: Bedroom 1
  • Room Level: Second
Room 7
  • Room Type: Bedroom 2
  • Room Level: Second
Room 8
  • Room Type: Bedroom 3
  • Room Level: Second
Room 9
  • Room Type: Full Bathroom
  • Room Level: Second
Rental
Rental Information
  • Certified Occupancy No: Yes

Property History for 386 Cheshire Road

DateEvent & SourcePriceAppreciation
Nov 2, 2025

Listed (Active)

Berkshire County Board of REALTORS #248155

$399,900
Mar 21, 2002

Sold (Public Record)

Public Record #100890108

$117,000
Mar 20, 2002

Sold

Berkshire County Board of REALTORS #156155

$117,000
Jan 2, 2002

Listed (Active)

Berkshire County Board of REALTORS #156155

$119,900
Jan 1, 2002

Expired

Berkshire County Board of REALTORS #155418

Oct 1, 2001

Listed (Active)

Berkshire County Board of REALTORS #155418

$139,900
DateEvent & SourcePrice
11/02/2025

Listed (Active)

Berkshire County Board of REALTORS #248155

$399,900
03/21/2002

Sold (Public Record)

Public Record #100890108

$117,000
03/20/2002

Sold

Berkshire County Board of REALTORS #156155

$117,000
01/02/2002

Listed (Active)

Berkshire County Board of REALTORS #156155

$119,900
01/01/2002

Expired

Berkshire County Board of REALTORS #155418

10/01/2001

Listed (Active)

Berkshire County Board of REALTORS #155418

$139,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 386 Cheshire Road

Taxable ValueLand$74,500Additions$136,200Total$210,700
Tax Record2025$3,780 ($315 / month)
Home Facts
Beds3Baths1.5Total Finished SqFt2,191 SqFtAbove Grade Finished SqFt2,191 SqFtStories2Lot Size22,895 SqFtStyleSingle Family ResidenceYear Built1932Year Renovated1984ZoningR12CountyBERKSHIREAPNPITT M:L16 B:0002 L:003

Schools near 386 Cheshire Road

This home is within Pittsfield School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - 1 to 12
Rating
School
Distance
Allendale Elementary School
PublicPK to 5

John T Reid Middle School
Public6 to 8

Pittsfield High School
Public9 to 12

Pittsfield Public Virtual Academy
Public1 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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386 Cheshire Road is a single family home for sale in Pittsfield, MA 01201. This property was listed for sale on November 2, 2025 by ASHMERE REALTY, INC., it's currently listed at $399,900. It has been on the market for a total of 52 days and was last sold on March 21, 2002. This listing's school district is Pittsfield School District. Nearby schools include Allendale Elementary School, John T Reid Middle School and Pittsfield High School. 386 Cheshire Road is a 3-bed, 2-bath, 2,191 sqft single family home built in 1932.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of ASHMERE REALTY, INC., Debra Goddeau

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.