For sale

$385,000

Est. $2,731/mo —

•

2,170

sq ft

118 Winesap Rd, Pittsfield, MA 01201

About this home

Opportunity awaits in this spacious 4-bedroom, 3-bath Colonial located in the highly sought-after Orchard neighborhood. Offering generous room sizes throughout, this home features a welcoming family room with a fireplace and skylights that fill the space with natural light. The convenient first-floor laundry enhances everyday living. The partially finished basement provides additional flexible space for recreation, a home office, or storage. Recent updates include newer carpeting and a newer roof, offering a solid foundation for future improvements. Outside, enjoy a fenced backyard with a deck. While the home could benefit from some TLC and cosmetic updates, it presents an excellent opportunity to build equity and customize to your taste in a prime location.

Single-familyProperty Type

1986Year Built

0.4 acresLot Size

$177Price/Sq.Ft.

Listed by Robin Moore • 413 REAL ESTATE

Listing updated: Aug 15, 2026 at 09:30pm

Redfin checked: a minute ago

•Source:BCMLS #249774

Payment calculator

$2,731 per month

Principal and interest$2,023

Property taxes

$654

HOA dues

Home insurance

$55

Utilities

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Nearby open houses (3)

Around this home

Schools

K - 12
Preschool & daycare

Williams Elementary School

Public PreK-5 • Assigned • 0.9mi

6/10

Theodore Herberg Middle School

Public 6-8 • Assigned • 2.2mi

3/10

Pittsfield High School

Public 9-12 • Assigned • 2.4mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

118 Winesap Rd · $385,000

Strong offer

$385K and above

75% chance or better to win

Why $385K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 41 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Dishwasher
Refrigerator
Carpet, linoleum, and wood flooring

Bedrooms
8 total rooms (bedroom count not specified separately)

Bathrooms
3 full bathrooms

Kitchen
Includes dishwasher and refrigerator

Laundry & utility
100 Amp electric service

Flooring
Carpet
Linoleum
Wood

Heating & cooling
Natural gas heating

Sale and tax history for 118 Winesap Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$6,839 (+12.8%)

$92,700 + $280,600

$373,300

2022

$6,064 (−1.2%)

$82,700 + $244,000

$326,700

2021

$6,135 (+3.6%)

$82,700 + $236,000

$318,700

2020

$5,923 (+7.0%)

$72,700 + $227,800

$300,500

2019

$5,535 (+1.6%)

$72,700 + $212,300

$285,000

2018

$5,447 (+8.4%)

$67,700 + $204,500

$272,200

2017

$5,023 (+2.2%)

$59,200 + $196,700

$255,900

2016

$4,915 (+3.9%)

$59,200 + $202,800

$262,000

2015

$4,732

$59,200 + $202,800

$262,000

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.4 Acres

Year renovated

—

Finished Sq. Ft.

2,170

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,170

Year built

1986

Style

Single Family Residential

County

Berkshire County

APN

2729014

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

2/10 Heat Factor

7 days above 90° expected this year, 16 days in 30 years

4/10 Wind Factor

9% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Pittsfield, MA • 01201

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

93/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.3 hrs

5.9 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 118 Winesap Rd

$371,229

$14K under list price of $385K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $350K to $455K.

SOLD MAY 28, 2026
$349,999 Last sold price
3 beds1.5 baths1,940 sq ft
1842 East St, Pittsfield, MA 01201
$3/sq ft
smaller lot
29 years older
SOLD JUN 15, 2026
$405,000 Last sold price
4 beds3 baths2,870 sq ft
40 Baldwin Ave, Pittsfield, MA 01201
$36/sq ft
smaller lot
8 years older
SOLD JUN 15, 2026
$455,000 Last sold price
4 beds3 baths2,530 sq ft
43 Baldwin Ave, Pittsfield, MA 01201
$3/sq ft
smaller lot
18 years older
SOLD JAN 7, 2026
$400,000 Last sold price
4 beds2 baths1,876 sq ft
26 Leona Dr, Pittsfield, MA 01201
$36/sq ft
smaller lot
14 years older
SOLD AUG 5, 2026
$359,000 Last sold price
3 beds1.5 baths1,560 sq ft
15 Lillian St, Pittsfield, MA 01201
$53/sq ft
smaller lot
31 years older
SOLD FEB 27, 2026
$392,500 Last sold price
4 beds2 baths1,470 sq ft
100 Elaine Dr, Pittsfield, MA 01201
$90/sq ft
smaller lot
24 years older

Rental earnings

Est. $3,871 per month, based on comparable rentals

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