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$389,900

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,191 Sq. Ft.
  • 0.53 Acres
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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 with 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.

Full Property Details for 386 Cheshire Rd

General

  • Price: $389,900
  • Taxes: $3,780 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 1109
  • MLS ID: 248155
  • Updated: 1/2/2026
  • Added to Site: 75 day(s) ago

Interior

  • Number of Rooms: 6
  • Interior Features: Cable Available, Walk-In Closet(s)
  • Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer
  • Flooring: Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Exterior

  • Exterior Features: Trash Public, Curbside Recycling, Bus-Public, Fenced-Partially, Outbuilding, Patio

Parking

  • Parking Features: Off Street
  • Other Parking Type: Off Street

Location

  • Area: Middle Registry

Heating & Cooling

  • Heating Type: Nat Gas, Boiler, Hot Water

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Colonial
  • Roof: Asphalt Shingles
  • Square Feet: 2,191
  • Year Built: 1932
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 0.53
  • Lot Size (Sq. Ft.): 23,087
  • Lot Dimensions: 22, 895 sqft
  • Zoning: Residential

Financial Considerations

  • Tax Amount: $3,780
  • Tax Year: 2025

Disclosures and Reports

  • Property ID: PITT M:L16 B:0002 L:003

Listed by Ashmere Realty, Inc., Debra A Goddeau

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Listing agent

— 386 Cheshire Rd —

  • Debra A Goddeau

    Ashmere Realty, Inc.

413-655-0003

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 386 Cheshire Rd

School District:Pittsfield School District, Pittsfield, MA
NameGradesDistance
Allendale Elementary School
180 Connecticut Avenue, Pittsfield, MA 01201
K-51.7 mi
John T Reid Middle School
950 North Street, Pittsfield, MA 01201
6-82.3 mi
Pittsfield High School, Pittsfield, MA
300 East Street, Pittsfield, MA 01201
9-123.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 386 Cheshire Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/02/2026
Price Reduced
$389,900
-2.5%
MLS
11/02/2025
Listed
$399,900
241.79%
MLS
3/21/2002
Sold
$117,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 386 Cheshire Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,780
8%
$210,700
11%
2024
$3,513
5%
$190,400
4%
2023
$3,347
8%
$182,700
9%
2022
$3,098
13%
$166,900
17%
2021
$2,739
6%
$142,300
8%
2020
$2,596
—
$131,700
-1%
2019
$2,591
-1%
$133,400
2%
2018
$2,617
2%
$130,800
—
2017
$2,562
5%
$130,500
—
2016
$2,450
4%
$130,600
—
2015
$2,359
2%
$130,600
-4%
2014
$2,322
—
$135,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 386 Cheshire Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Ashmere Realty, Inc., Debra A Goddeau

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386 Cheshire Rd, Pittsfield, MA 01201 (MLS# 248155) is a Single Family property with 3 bedrooms and 2 full bathrooms. 386 Cheshire Rd is currently listed for $389,900 and was received on November 02, 2025. Want to learn more about 386 Cheshire Rd? Do you have questions about finding other Single Family real estate for sale in Pittsfield? You can browse all Pittsfield real estate or contact a Coldwell Banker agent to request more information.

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