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.
Pending
Price cut: $10K (1/2)
$389,900
386 Cheshire Rd, Pittsfield, MA 01201
3beds
2,191sqft
Est.:
Single Family Residence
Built in 1932
0.53 Acres Lot
$378,500 Zestimate®
$178/sqft
$-- HOA
What's special
Warm and inviting atmosphereExpansive primary bedroomBeautifully renovated home
- 121 days |
- 104 |
- 5 |
Zillow last checked: 8 hours ago
Listing updated: January 21, 2026 at 12:15pm
Listed by:
Debra A Goddeau 413-655-0003,
ASHMERE REALTY, INC.
Source: BCMLS,MLS#: 248155
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Bedroom 1
- Level: Second
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Full bathroom
- Level: First
Full bathroom
- Level: Second
Dining room
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Mud room
- Level: First
Heating
- Nat Gas, Boiler, Hot Water
Appliances
- Included: Dishwasher, Dryer, Range, Refrigerator, Washer
Features
- Walk-In Closet(s)
- Flooring: Ceramic Tile, Laminate
- Basement: Walk-Out Access,Unfinished,Interior Entry,Concrete
Interior area
- Total structure area: 2,191
- Total interior livable area: 2,191 sqft
Property
Parking
- Parking features: Off Street
- Details: Off Street
Features
- Patio & porch: Patio
- Exterior features: Curbside Recycling, Bus-Public
- Fencing: Partial
Lot
- Size: 0.53 Acres
Details
- Additional structures: Outbuilding
- Parcel number: PITT M:L16 B:0002 L:003
- Zoning description: Residential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Roof: Asphalt Shingles
Condition
- Year built: 1932
Utilities & green energy
- Electric: 200 Amp
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Trash Public, Cable Available
Community & HOA
Location
- Region: Pittsfield
Financial & listing details
- Price per square foot: $178/sqft
- Tax assessed value: $210,700
- Annual tax amount: $3,780
- Date on market: 11/3/2025
Estimated market value
$378,500
$360,000 - $397,000
$2,685/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/21/2026 | Pending sale | $389,900$178/sqft |
Source:  BCMLS #248155 Report a problem | ||
| 1/2/2026 | Price change | $389,900-2.5%$178/sqft |
Source: BCMLS #248155 Report a problem | ||
| 11/3/2025 | Listed for sale | $399,900+241.8%$183/sqft |
Source: BCMLS #248155 Report a problem | ||
| 3/21/2002 | Sold | $117,000$53/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $3,780 +7.6% | $210,700 +10.7% |
| 2024 | $3,513 +5% | $190,400 +4.2% |
| 2023 | $3,347 +8% | $182,700 +9.5% |
| 2022 | $3,098 +13.1% | $166,900 +17.3% |
| 2021 | $2,739 +5.5% | $142,300 +8% |
| 2020 | $2,596 +0.2% | $131,700 -1.3% |
| 2019 | $2,591 -1% | $133,400 +2% |
| 2018 | $2,617 +2.1% | $130,800 +0.2% |
| 2017 | $2,562 +4.6% | $130,500 -0.1% |
| 2016 | $2,450 +3.9% | $130,600 |
| 2015 | $2,359 +0% | $130,600 -3.5% |
| 2014 | $2,359 +4.3% | $135,400 |
| 2013 | $2,261 +3.7% | $135,400 |
| 2012 | $2,181 +2.5% | $135,400 -3.4% |
| 2011 | $2,128 +4.2% | $140,100 -2.6% |
| 2010 | $2,043 +1.2% | $143,900 -2.5% |
| 2009 | $2,018 +4% | $147,600 |
| 2008 | $1,941 -19.7% | $147,600 -13% |
| 2007 | $2,417 +1.2% | $169,600 +11.1% |
| 2006 | $2,388 +1.6% | $152,600 +1.6% |
| 2005 | $2,351 +6.3% | $150,200 +37.4% |
| 2004 | $2,212 +0.9% | $109,300 -0.3% |
| 2003 | $2,193 +4.2% | $109,600 +6.2% |
| 2001 | $2,104 +23.1% | $103,200 +1.8% |
| 1996 | $1,709 | $101,400 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,250/mo
Principal & interest
$1860
Property taxes
$390
Climate risks
Neighborhood: 01201
Nearby schools
GreatSchools rating
- 4/10Allendale Elementary SchoolGrades: PK-5Distance: 1.7 mi
- 3/10John T Reid Middle SchoolGrades: 6-8Distance: 2.3 mi
- 3/10Taconic High SchoolGrades: 9-12Distance: 3.9 mi
Schools provided by the listing agent
- Elementary: Allendale
- Middle: John T Reid
- High: Taconic
Source: BCMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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