Google street view image for 99 Winesap Rd, Pittsfield, MA 01201

Off market aug 1985 for $125K

$473,412

Est. refi paymentEst. refi $824/mo

•

3 ba

•

2,128

sq ft

99 Winesap Rd, Pittsfield, MA 01201

About this home

99 Winesap Rd is a 2,128 square foot house on a 0.29 acre lot with 3 bedrooms and 3 bathrooms. - it last sold on August 01, 1985 for $125,000. Based on Redfin's Pittsfield data, we estimate the home's value is $473,412.

Single-familyProperty Type

1985Year Built

0.29 acresLot Size

$222Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$473,412

$348K since sold in August 1985$4,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.7% higher than the average sale price ($392K) of 6 comparable homes.

SOLD JUL 23, 2026
$400,000
A
3 beds2 baths1,898 sq ft
18 Greenings Ave, Pittsfield, MA 01201
SOLD MAR 10, 2026
$415,000
B
3 beds2.5 baths2,299 sq ft
86 Winesap Rd, Pittsfield, MA 01201
SOLD AUG 31, 2026
$371,000
C
3 beds2 baths1,728 sq ft
18 Elaine Ave, Dalton, MA 01226
SOLD OCT 17, 2025
$400,000
D
3 beds3 baths2,109 sq ft
2 Caratina Ave, Pittsfield, MA 01201
SOLD SEP 25, 2026
$375,000
E
3 beds2.5 baths2,200 sq ft
56 Saratoga Dr, Pittsfield, MA 01201
SOLD SEP 23, 2026
$392,000
F
3 beds2.5 baths2,100 sq ft
149 Longview Ter, Pittsfield, MA 01201

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Earn from this home

Refinance

Est. cash available

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Rent

$3,593/mo

Redfin rental estimate

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Market trends in 01201, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.8%

0.6% MoM

Median sale price

$317K

$6K MoM

Avg. days on market

37d

1 days MoM

Recently sold homes

143

11 MoM

New listings for sale

OPEN OCT 20, 4:30PM TO 6PM
$342,000
2 beds2 baths1,144 sq ft
33 Highlawn Dr, Pittsfield, MA 01201
NEW 4 HRS AGO
$372,900
3 beds1 bath1,144 sq ft
92 Noblehurst Ave, Pittsfield, MA 01201
NEW 14 HRS AGO
$287,000
5 beds2.5 baths2,618 sq ft
37 Adam St, Pittsfield, MA 01201
NEW 15 HRS AGO
$339,900
2 beds1 bath1,086 sq ft
34 Sampson Pkwy, Pittsfield, MA 01201
NEW 22 HRS AGO
$349,900
3 beds2 baths1,828 sq ft
90 Orlando Ave, Pittsfield, MA 01201
OPEN SUN, 10AM TO 11:30AM
$469,000
3 beds2 baths1,789 sq ft
44 Melbourne Rd, Pittsfield, MA 01201
NEW 28 HRS AGO
$130,000
6 beds2 baths2,192 sq ft
86 Madison Ave, Pittsfield, MA 01201
NEW 29 HRS AGO
$369,000
3 beds2.5 baths1,378 sq ft
44 Michael Dr, Pittsfield, MA 01201
$579,000
3 beds3 baths2,214 sq ft
852 Churchill St, Pittsfield, MA 01201
COMING SOON
$284,900
2 beds1.5 baths660 sq ft
189 Mohegan St, Pittsfield, MA 01201
See all

Provided by Redfin

Sale history for 99 Winesap Rd

Year

Property tax

Land + Additions

Assessment*

2023

$7,392 (+12.9%)

$90,900 + $312,600

$403,500

2022

$6,546 (−1.2%)

$80,900 + $271,800

$352,700

2021

$6,624 (+3.5%)

$80,900 + $263,200

$344,100

2020

$6,402 (+10.5%)

$70,900 + $253,900

$324,800

2019

$5,793 (+1.5%)

$70,900 + $227,400

$298,300

2018

$5,705 (+8.3%)

$65,900 + $219,200

$285,100

2017

$5,267 (+2.3%)

$57,400 + $210,900

$268,300

2016

$5,151 (+3.9%)

$57,400 + $217,200

$274,600

2015

$4,959

$57,400 + $217,200

$274,600

Tax history for 99 Winesap Rd

Year

Property tax

Land + Additions

Assessment*

2023

$7,392 (+12.9%)

$90,900 + $312,600

$403,500

2022

$6,546 (−1.2%)

$80,900 + $271,800

$352,700

2021

$6,624 (+3.5%)

$80,900 + $263,200

$344,100

2020

$6,402 (+10.5%)

$70,900 + $253,900

$324,800

2019

$5,793 (+1.5%)

$70,900 + $227,400

$298,300

2018

$5,705 (+8.3%)

$65,900 + $219,200

$285,100

2017

$5,267 (+2.3%)

$57,400 + $210,900

$268,300

2016

$5,151 (+3.9%)

$57,400 + $217,200

$274,600

2015

$4,959

$57,400 + $217,200

$274,600

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Basement Information
Basement Type: Full

Bathroom Information
# of Full Baths: 2
# of 1/2 Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Room Information
# of Rooms: 8

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Exterior Wall: Aluminum/Vinyl

Property Information
Subdivision Name: BERKSHIRE LAND DEV CO
Living Sq. Ft: 2,128
Gross Sq. Ft: 2,128
Ground Floor Sq. Ft: 1,064
# of Units: 1
# of Stories: 2

Parking & Garage Information
Parking Type: Attached Garage
Garage / Carport Type: Attached

Lot Information
# of Buildings: 1
Land Sq. Ft: 12,632
Municipality Name: PITTSFIELD
Acres: 0.29
Zoning Code: R12
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 2,128
Stories: 2.0
Lot Size: 0.29 acres
Style: Single Family Residential
Year Built: 1985
Year Renovated: —
County: Berkshire County
APN: 2728987

Home facts updated by county records on Jul 19, 2023

Around this home

Schools

Williams Elementary School

Public PreK-5 • Assigned • 1.0mi

6/10

Theodore Herberg Middle School

Public 6-8 • Assigned • 2.3mi

3/10

Pittsfield High School

Public 9-12 • Assigned • 2.4mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

3/10 Heat Factor

7 days above 90° expected this year, 17 days in 30 years

4/10 Wind Factor

10% 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

In this area, properties receive around 8.5 hours in June and 3.8 hours in December, placing it below the U.S. average for solar exposure.

8.5 hrs

3.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$450,000 – $545,000

Sell confidently with a local market expert in Pittsfield. 3 minutes to get started.

Nearby similar homes

OPEN OCT 20, 4:30PM TO 6PM

$342,000

2 beds2 baths1,144 sq ft

33 Highlawn Dr, Pittsfield, MA 01201

$385,000

4 beds1.5 baths2,203 sq ft

774 Main St, Dalton, MA 01226

$349,500

3 beds2 baths1,961 sq ft

5 Putnam Ave, Pittsfield, MA 01201

$439,000

4 beds3.5 baths1,800 sq ft

4 Caratina Dr, Pittsfield, MA 01201

$549,900

4 beds2.5 baths2,670 sq ft

48 Brookside Dr, Pittsfield, MA 01201

OPEN SUN, 12:30PM TO 2PM

$298,000

3 beds1.5 baths1,363 sq ft

232 Dalton Ave, Pittsfield, MA 01201

New listings for sale in 01201

OPEN OCT 20, 4:30PM TO 6PM

$342,000

2 beds2 baths1,144 sq ft

33 Highlawn Dr, Pittsfield, MA 01201

NEW 4 HRS AGO

$372,900

3 beds1 bath1,144 sq ft

92 Noblehurst Ave, Pittsfield, MA 01201

NEW 14 HRS AGO

$287,000

5 beds2.5 baths2,618 sq ft

37 Adam St, Pittsfield, MA 01201

NEW 15 HRS AGO

$339,900

2 beds1 bath1,086 sq ft

34 Sampson Pkwy, Pittsfield, MA 01201

NEW 22 HRS AGO

$349,900

3 beds2 baths1,828 sq ft

90 Orlando Ave, Pittsfield, MA 01201

OPEN SUN, 10AM TO 11:30AM

$469,000

3 beds2 baths1,789 sq ft

44 Melbourne Rd, Pittsfield, MA 01201

NEW 28 HRS AGO

$130,000

6 beds2 baths2,192 sq ft

86 Madison Ave, Pittsfield, MA 01201

NEW 29 HRS AGO

$369,000

3 beds2.5 baths1,378 sq ft

44 Michael Dr, Pittsfield, MA 01201

$579,000

3 beds3 baths2,214 sq ft

852 Churchill St, Pittsfield, MA 01201

Home values near 99 Winesap Rd

Data from public records.

Address	Redfin Estimate
85 Winesap Road, Pittsfield, MA 4 Beds \| 2.5 Baths \| 1792 Sq. Ft.	$420,957
103 Winesap Road, Pittsfield, MA 4 Beds \| 2.5 Baths \| 2200 Sq. Ft.	$520,052

Address	Redfin Estimate
105 Winesap Road, Pittsfield, MA 4 Beds \| 2.5 Baths \| 1998 Sq. Ft.	$485,025
107 Winesap Road, Pittsfield, MA 3 Beds \| 2 Baths \| 2128 Sq. Ft.	$495,367

Address	Redfin Estimate
95 Winesap Road, Pittsfield, MA 3 Beds \| 2 Baths \| 2004 Sq. Ft.	$435,603
109 Winesap Road, Pittsfield, MA 4 Beds \| 2.5 Baths \| 1904 Sq. Ft.	$476,295

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